Journal articles: 'Indomethacin derivatives'

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Deng, Kui Lin, Chun Xiu Li, Ting Gao, et al. "Preparation and Drug Release Behavior from a Temperature-Sensitive Poly(aspartic Acid) Derivatives Hydrogel." Advanced Materials Research 711 (June 2013): 18–21. http://dx.doi.org/10.4028/www.scientific.net/amr.711.18.

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In this paper, a new pH/temperature-sensitive beads with semi-interpenetrating polymeric network based on sodium alginate(SA) and poly(aspartic acid) derivatives(M-E-PSI) were prepared using as drug delivery carrier. With indomethacin as a drug model，we investigated the release behaviors of indomethacin in different pH value, temperature and ratio of SA/ M-E-PSI. It turned out that the release amount of indomethacin in pH=2.1 phosphate buffer solution(PBS) was evidently higher than that in pH=7.4 PBS. And also, the release amount of indomethacin was also increased with increasing temperature and poly(aspartic acid) derivatives content in the beads.

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Abualhasan, Murad, Nidal Jaradat, Raghad Maslamani, Dana Nofal, and Linda Omar. "Synthesis of enhanced lipid solubility of indomethacin derivatives for topical formulations." Heterocyclic Communications 28, no. 1 (2022): 124–29. http://dx.doi.org/10.1515/hc-2022-0013.

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Abstract Indomethacin is a nonselective nonsteroidal anti-inflammatory drug with serious side effects such as depression, hallucination, and gastrointestinal irritation. This study aims to enhance indomethacin lipid solubility of indomethacin derivative to use it for the topical formulation since topical formulation may lower the unwanted side effects. The lipid solubility was achieved by adding various alkyl groups (methyl, ethyl, propyl, and isopropyl) to the drug via an ester linkage. The measured log p of these compounds was higher compared to the underivatized indomethacin. Furthermore, an ointment of each ester was formulated and was tested on mice skin using Franz diffusion. The best absorption was observed for methyl indomethacin with threefold increase in permeability compared to indomethacin. This study approves using derivatized indomethacin as a topical formulation with improved efficacy compared to the present gel formulation in the market.

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Lauro, Figueroa-Valverde, Díaz-Cedillo Francisco, García-Cervera Elodia, et al. "Activity Exerted by a Testosterone Derivative on Myocardial Injury Using an Ischemia/Reperfusion Model." BioMed Research International 2014 (2014): 1–11. http://dx.doi.org/10.1155/2014/217865.

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Some reports indicate that several steroid derivatives have activity at cardiovascular level; nevertheless, there is scarce information about the activity exerted by the testosterone derivatives on cardiac injury caused by ischemia/reperfusion (I/R). Analyzing these data, in this study, a new testosterone derivative was synthetized with the objective of evaluating its effect on myocardial injury using an ischemia/reperfusion model. In addition, perfusion pressure and coronary resistance were evaluated in isolated rat hearts using the Langendorff technique. Additionally, molecular mechanism involved in the activity exerted by the testosterone derivative on perfusion pressure and coronary resistance was evaluated by measuring left ventricular pressure in the absence or presence of the following compounds: flutamide, prazosin, metoprolol, nifedipine, indomethacin, and PINANE TXA2. The results showed that the testosterone derivative significantly increasesP=0.05the perfusion pressure and coronary resistance in isolated heart. Other data indicate that the testosterone derivative increases left ventricular pressure in a dose-dependent manner (0.001–100 nM); however, this phenomenon was significantly inhibitedP=0.06by indomethacin and PINANE-TXA2 P=0.05at a dose of 1 nM. In conclusion, these data suggest that testosterone derivative induces changes in the left ventricular pressure levels through thromboxane receptor activation.

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El-Gazzar, Abdel-Rahman, Hoda Hussein, and Hend Hafez. "Synthesis and biological evaluation of thieno[2,3-d]pyrimidine derivatives for anti-inflammatory, analgesic and ulcerogenic activity." Acta Pharmaceutica 57, no. 4 (2007): 395–411. http://dx.doi.org/10.2478/v10007-007-0032-6.

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Synthesis and biological evaluation of thieno[2,3-d]pyrimidine derivatives for anti-inflammatory, analgesic and ulcerogenic activity5-Methyl-6-phenyl-2-thioxothieno[2,3-d]pyrimidone derivative (2) reacted with hydrazonoyl chloride derivatives to afford triazolothienopyrimidones4a-f.Also, acetone-1-(2-amino-5-isopropyl-thiophene-3-carbonitrile) (3) reacted with functional and bifunctional groups to yield the corresponding compounds5-11. The new products showed anti-inflammatory, analgesic, and ulcerogenic activities comparable to that of indomethacin and acetylsalicylic acid, respectively.

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Kuźmycz, Olga, Aleksandra Kowalczyk, and Paweł Stączek. "Biological Activity of fac-[Re(CO)3(phen)(aspirin)], fac-[Re(CO)3(phen)(indomethacin)] and Their Original Counterparts against Ishikawa and HEC-1A Endometrial Cancer Cells." International Journal of Molecular Sciences 23, no. 19 (2022): 11568. http://dx.doi.org/10.3390/ijms231911568.

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Nonsteroidal anti-inflammatory drugs (NSAIDs) are inhibitors of cyclooxygenase enzyme (COX) and were found to have positive effects in reducing the risk of developing gynecological cancers. However, long-term administration of NSAIDs carries the risk of various side effects, including those in the digestive and circulatory systems. Therefore, there is a constant need to develop new NSAID derivatives. In this work, we investigated rhenium NSAIDs, comparing their effects on endometrial cancer cells with original NSAIDs, demonstrating the high activity of aspirin and indomethacin derivatives. The cytotoxic activity of rhenium derivatives against the Ishikawa and HEC-1A cancer cell lines was higher than that of the original NSAIDs. The IC50 after 24-h incubation of Ishikawa and HEC-1A were 188.06 µM and 394.06 µM for rhenium aspirin and 228.6 µM and 1459.3 µM for rhenium indomethacin, respectively. At the same time, IC50 of aspirin and indomethacin were 10,024.42 µM and 3295.3 µM for Ishikawa, and 27,255.8 µM and 5489.3 µM for HEC-1A, respectively. Moreover, these derivatives were found to inhibit the proliferation of both cell lines in a time- and state-dependent manner. The Ishikawa cell proliferation was strongly inhibited by rhenium aspirin and rhenium indomethacin after 72-h incubation (*** = p < 0.001), while the HEC-1A proliferation was inhibited by the same agents already after 24-h incubation (*** = p < 0.001). Furthermore, the ROS level in the mitochondria of the tested cells generated in the presence of rhenium derivatives was higher than the original NSAIDs. That was associated with rhenium indomethacin exclusively, which had a significant effect (*** = p < 0.001) on both Ishikawa and HEC-1A cancer cells. Rhenium aspirin had a significant effect (*** = p < 0.001) on the mitochondrial ROS level of Ishikawa cells only. Overall, the research revealed a high potential of the rhenium derivatives of aspirin and indomethacin against endometrial cancer cells compared with the original NSAIDs.

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Serra Moreno, Judith, Dimitrios Agas, Maria Giovanna Sabbieti, Matteo Di Magno, Antonella Migliorini, and M. Antonietta Loreto. "Synthesis of novel pyrrolyl-indomethacin derivatives." European Journal of Medicinal Chemistry 57 (November 2012): 391–97. http://dx.doi.org/10.1016/j.ejmech.2012.09.008.

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Mahdi, Monther Faisal, Ashour H. Dawood, and Ahmed Kareem Hussein. "Design, Synthesis and Preliminary Pharmacological Evaluation of Mutual Prodrug of Non-Steroidal Anti-Inflammatory Drugs Coupling With Natural Anti-Oxidants Via Glycine." Al Mustansiriyah Journal of Pharmaceutical Sciences 13, no. 1 (2013): 155–69. http://dx.doi.org/10.32947/ajps.v13i1.211.

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Non-steroidal anti-inflammatory drugs (NSAIDs); naproxen and indomethacin have been conjugated with different antioxidants (thymol, menthol & guaiacol) having antiulcerogenic activity via glycine amino acid as spacer with the objective of obtaining NSAIDs-glycine- antioxidant prodrugs as gastrosparing NSAIDs devoid of ulcerogenic side effects and synergistically with anti-inflammatory action of glycine. Four mutual prodrugs (IIV) were synthesized using glycine as spacer and their structures were confirmed and characterized using elemental microanalysis (CHNO), IR, and some physiochemical properties.Invivo acute anti-inflammatory activity of the compounds (I & II) (naproxen derivatives) and the compounds (III & IV) (indomethacin derivatives) was evaluated in rat using an egg-white induced edema model of inflammation in a dose equivalent to 2.5 mg/Kg of naproxen, and 2 mg/Kg of indomethacin respectively.All tested compounds produced significant reduction of paw edema with respect to the effect of propylene glycol 50% v/v (control group). Moreover, the activity of compound III was significantly higher than that of indomethacin (at 2 mg/Kg), while compound IV expressed a comparable effect to that of indomethacin in the (120–300) minute time of the experiment, while compounds I&II was showed a comparable effect to that of naproxen at (180-300) minute time interval of the experiment. The result of this study indicates that these mutual prodrugs of naproxen & indomethacin maintained or may enhanced their antiinflammatory activity.

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Benedek, G., P. Tóth-Daru, J. Janáky, A. Hortobágyi, F. Obál, and K. Colner-Sasi. "Indomethacin is Effective Against Neurogenic Hyperthermia Following Cranial Trauma or Brain Surgery." Canadian Journal of Neurological Sciences / Journal Canadien des Sciences Neurologiques 14, no. 2 (1987): 145–48. http://dx.doi.org/10.1017/s0317167100026275.

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Abstract:The effectiveness of indomethacin treatment (1 mg/kg) as an antipyretic was tested in patients after cranial trauma or brain surgery involving the centromedial forebrain. Indomethacin was effective in reducing temperature in 10 of 11 cases which showed a dipyrone-resistant hyperthermia developing in the first 24 hours after brain damage, while no significant antipyretic effect was seen in hyperthermic cases developing more than 72 hours after cranial trauma or brain surgery. Biochemical tests estimating the effect of indomethacin, and pyrazolone derivatives on the arachidonic acid metabolism showed significant effects of indomethacin only in influencing cyclooxygenase activity and no effect of any drugs on lipoxy — genase actions. In view of these observations, the use of indomethacin is recommended as a treatment for neurogenic hyperthermia.

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El-Kashef, Hussein, Talaat El-Emary, Pierre Verhaeghe, Patrice Vanelle, and Maha Samy. "Anticancer and Anti-Inflammatory Activities of Some New Pyrazolo[3,4-b]pyrazines." Molecules 23, no. 10 (2018): 2657. http://dx.doi.org/10.3390/molecules23102657.

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New derivatives of pyrazolo[3,4-b]pyrazines and related heterocycles were synthesized using 5-amino-3-methyl-4-nitroso-1-phenyl-pyrazole (1) as a starting material. The 5-acetyl derivative 15 was shown to be a useful key intermediate for the synthesis of several derivatives of pyrazolopyrazines. Some of the prepared compounds were evaluated for their anti-inflammatory and anti-breast cancer MCF-7 cell line activities. SAR study showed that compounds 15 and 29 exhibited remarkable anti-inflammatory activity, where 15 showed the same activity as that of the reference drug indomethacin. On the other hand, compounds 25i, 25j showed very significant inhibitory activity (p < 0.001) against MCF-7 breast cancer cell line.

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Haskologlu, Ismail Celil, Emine Erdag, Ahmet Ozer Sehirli, Orhan Uludag, and Nurettin Abacioglu. "Exploring the Therapeutic Potential of Benzoxazolone Derivatives on the Circadian Clock: An In Silico and Hypothetical Approach." Chronobiology in Medicine 6, no. 2 (2024): 87–99. http://dx.doi.org/10.33069/cim.2024.0012.

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Objective: Pain conditions exhibit variations linked to circadian rhythms. Circadian rhythms, regulated by clock proteins, impact melatonin levels and immune functions. Melatonin, structurally similar to indomethacin, a non-steroidal anti-inflammatory drug, serves as an alternative in pain-related conditions. Literature suggests a correlation between melatonin-dependent regulation of circadian rhythm and reductions in pain complaints. 2(3H)-Benzoxazolone, known for its anti-inflammatory and analgesic properties, is a promising scaffold for drug design. In this study, pharmacophore analysis focused on benzoxazolone derivatives, evaluating their impact on clock proteins, and providing insights into potential chronotherapeutic implications. Methods: Molecular docking and dynamics simulations were conducted on CLOCK:BMAL1, PER1, PER2, CRY1, and CRY2 clock proteins using benzoxazolone and its 5-substituted derivatives. Molecular mechanics/Poisson–Boltzmann surface area (MM/PBSA) calculations were employed to analyze binding free energies. Benzoxazolone derivatives, especially 5-nitro-2-benzoxazolone and 5-fluoro-2-benzoxazolone, exhibited elevated binding affinities on clock proteins compared to melatonin and indomethacin, the reference molecules. The interaction profiles and stability of complexes were maintained throughout the simulations. Results: The results suggest a regulatory impact on CRY proteins, emphasizing their role in circadian rhythm and pain modulation. In addition, the benzoxazolone ring and its derivatives, structurally resembling the core structure of melatonin and indomethacin, demonstrate promising affinities on clock proteins. Conclusion: These findings provide preliminary data and hypothetically propose benzoxazolone derivatives as potential candidates for dual functionality in analgesic activity and circadian rhythm regulation, warranting further in vitro and clinical investigations.

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Gibson, P. R., and D. P. Jewell. "Sulphasalazine and Derivatives, Natural Killer Activity and Ulcerative Colitis." Clinical Science 69, no. 2 (1985): 177–84. http://dx.doi.org/10.1042/cs0690177.

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1. The effects of sulphasalazine, 5-aminosalicylic acid (5-ASA), sulphapyridine and azodisalicylic acid (ADS) in vitro on the natural killer (NK) activity of peripheral blood mononuclear cells (MNC) have been examined and compared with those of the lipoxygenase inhibitor, nordihydroguaiaretic acid (NDGA) and the cyclooxygenase inhibitor, indomethacin. 2. Sulphasalazine, sulphapyridine and ADS inhibited NK activity with 50% inhibitory concentrations (IC50) of 0.7, 2.5 and 4.0 mmol/l respectively. The effect was rapidly reversible. In contrast, 5-ASA minimally inhibited NK activity at 50 mmol/l only. 3. NDGA potently inhibited NK activity (IC50 27 μmol/l) but this was only partly reversible in short term incubations. Indomethacin had no effect at concentrations less than those inhibiting cyclo-oxygenase activity (1-10 μmol/l) but potently and reversibly inhibited NK activity at or above 25 μmol/l. 4. The inhibitory effects observed were unlikely to be due to direct toxicity of effector cells as 5-ASA, sulphapyridine and ADS had no effect on the viability of peripheral blood MNC, whereas NDGA and indomethacin lysed MNC only at maximal concentrations tested. Though sulphasalazine produced MNC lysis at and above 1 mmol/l, the rapid reversibility of the inhibition of NK activity at 1 mmol/l suggested that lysis of NK cells contributed little to the suppressive effect at this concentration. 5. The disparity of the therapeutic efficacy and effects on NK activity of sulphasalazine and its derivatives in vitro may suggest that NK activity is not a major pathogenic mechanism in ulcerative colitis. Any inhibitory effect on cellular immune function of indomethacin does not necessarily reflect an effect of cyclo-oxygenase inhibition.

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Garg, Ajay Kumar, Ranjan Kumar Singh, Vaibhav Saxena, Saurabh Kr Sinha, and Sanjay Rao. "Synthesis, Characterization, and Anti-inflammatory activity of Some Novel Oxazole Derivatives." Journal of Drug Delivery and Therapeutics 13, no. 1 (2023): 26–28. http://dx.doi.org/10.22270/jddt.v13i1.5719.

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A series of novel oxazole derivatives (A, A1, A2) were synthesized starting from acetone and urea. The compound (A) was obtained by heating it with acetophenone and urea in iodine. Compound (A) on treatment with 4-amino benzaldehyde (Z)-N-(4-amino benzylidine)-4-((E)-Penta-2, 4-diene-2) oxazole-2-amine afforded (A1). Acylation of compound (A) with 4-amino benzoyl chloride to obtain the corresponding N-(4 phenyl oxazole-2- yl)- benzamide (A2). The structures of compounds have been established employing FTIR and 1H-NMR spectral analysis. All oxazole derivatives were evaluated for anti-inflammatory activity by the carrageenan-induced Rat hind paw method. Derivative A1 shows maximum anti-inflammatory activity. Keywords: Oxazoles, anti-inflammatory, Benzamide, acetophenone, indomethacin.

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Dvořáková, Kristýna, Petr Štěpánek, Jiřina Kroupová, and Jarmila Zbytovská. "N-Alkylmorpholines: Potent Dermal and Transdermal Skin Permeation Enhancers." Pharmaceutics 14, no. 1 (2021): 64. http://dx.doi.org/10.3390/pharmaceutics14010064.

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Transdermal drug delivery is an attractive non-invasive method offering numerous advantages over the conventional routes of administration. The main obstacle to drug transport is, however, the powerful skin barrier that needs to be modulated, for example, by transdermal permeation enhancers. Unfortunately, there are still only a few enhancers showing optimum properties including low toxicity and reversibility of enhancing effects. For this reason, we investigated a series of new N-alkylmorpholines with various side chains as potential enhancers in an in vitro permeation study, using three model permeants (theophylline, indomethacin, diclofenac). Moreover, electrical impedance, transepidermal water loss, cellular toxicity and infrared spectroscopy measurements were applied to assess the effect of enhancers on skin integrity, reversibility, toxicity and enhancers’ mode of action, respectively. Our results showed a bell-shaped relationship between the enhancing activity and the hydrocarbon chain length of the N-alkylmorpholines, with the most efficient derivatives having 10–14 carbons for both transdermal and dermal delivery. These structures were even more potent than the unsaturated oleyl derivative. The best results were obtained for indomethacin, where particularly the C10-14 derivatives showed significantly stronger effects than the traditional enhancer Azone. Further experiments revealed reversibility in the enhancing effect, acceptable toxicity and a mode of action based predominantly on interactions with stratum corneum lipids.

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Mustafa Taha Abdull, Monther F. Mahdi, and Ayad k. Khan. "Molecular docking, Synthesis and Characterization of New Indomethacin and Mefenamic Acid Analogues as Potential Anti-inflammatory Agents." Al Mustansiriyah Journal of Pharmaceutical Sciences 23, no. 3 (2023): 336–44. http://dx.doi.org/10.32947/ajps.v23i3.1052.

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In this work the pharmacological study and synthesis of new thiadiazine bearing on triazole which obtained from hippuric acid , indomethacin and mefenamic acid that have carboxylic acid moiety, Drugs with carboxylic groups and thiocarbohydrazide interacted to produce the 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol (1a-c). and the starting products 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol) were treated with chloroacetyl chloride to produce final products (2a-c). To confirm the structure of the generated compounds, FT-IR, 1H-NMR, and mass spectroscopy were used to characterize all derivatives (intermediate and final products). The in vivo anti-inflammatory efficacy of some derivatives and thier toxicity to animals (in vivo) were evaluated. And then derivatives were subjected to molecular docking to create safe and efficient molecules. To test each derivative's ability to bind to the enzyme's active site, it was docked into the active sites. To determine the synthetic compound's topological polar surface area, bioavailability, and drug-likeness, An investigation of absorption, distribution, metabolism and elimination was performed. According to the findings, the tested derivatives adhered to the Lipinski rule and were ingested

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Nora, Amer Hussien, Y. Hussien Hyffaa, and H. Abdulrahman Shaymaa. "Predictive biological activity of newly synthesized hydrazone compounds derived from indomethacin." Journal of Wildlife and Biodiversity 7, Special Issue (2023): 391–402. https://doi.org/10.5281/zenodo.10246323.

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New derivatives of hydrazone have been successfully created, specifically 2-(1-(Aryl)-5-methoxy-2-methyl-1H-indol-3-yl)-N'-(2-chlorobenzylidene) acetohydrazide. The transformation of Indomethacin ester into hydrazide was achieved through a reaction with hydrazine hydrate in absolute ethanol, followed by the reaction of the resulting hydrazide with aromatic aldehydes. The structures of these newly synthesized hydrazones were validated through IR, 1HNMR, and 13CNMR analyses. Each compound's energies were optimized by utilizing density functional theory (DFT) for theoretical calculations. By employing a quantitative structure-activity relationship (QSAR) mathematical model, this optimization enables the prediction of the biological activity of the compounds. Therefore, this research centers on the synthesis and characterization of hydrazone derivatives of Indomethacin, emphasizing the use of QSAR modeling to connect biological activity and molecular structure. The study sheds light on the methods employed for compound synthesis and characterization, contributing valuable insights into the properties and potential applications of these innovative derivatives through the application of computational chemistry.

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Al-Masoudi, Najim A., Nadhir N. A. Jafar, Layla J. Abbas, Sadiq J. Baqir, and Christophe Pannecouque. "Synthesis and anti-HIV Activity of New Benzimidazole, Benzothiazole and Carbohyrazide Derivatives of the anti-Inflammatory Drug Indomethacin." Zeitschrift für Naturforschung B 66, no. 9 (2011): 953–60. http://dx.doi.org/10.1515/znb-2011-0914.

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There is an urgent need for the design and development of new and safer drugs for the treatment of HIV infection, active against the currently resistant viral strains. New derivatives of the non-steroidal anti-inflammatory drug indomethacin bearing benzimidazoles, benzothiazole, purine and pyridine residues 8 - 13 were synthesized with the aim of developing new non-nucleoside reverse transcriptase inhibitors (NNRTIs).Alternatively, new imine analogs 16 - 20 were synthesized from condensation of indomethacinyl hydrazide 15, prepared from the ester 14, with various ketone precursors. Treatment of 15 with phenyl isothiocyanate or triethyl orthoformate afforded the phenylcarbonothioyl and the oxadiazole derivatives 21 and 22, respectively. The new compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 9 and 10 were the most active in inhibiting HIV-2 and HIV-1, respectively, with EC50 ≥ 17.60 μgmL−1 and > 1.15 μgmL−1 (therapeutic indexes (SI) of ≥ 3 and < 1, respectively), and are leading candidates for further development.

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Mohamed, Mosaad S., Aymn E. Rashad, Mostafa Adbel-Monem, and Samar S. Fatahalla. "New Anti-Inflammatory Agents." Zeitschrift für Naturforschung C 62, no. 1-2 (2007): 27–31. http://dx.doi.org/10.1515/znc-2007-1-205.

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The pyrrole derivatives 1a, b and 2a, b were used as precursors for the preparation of N-substituted pyrrole derivatives 3a, b-9a, b and pyrrolo[2,3-d]pyrimidines 13-16. Also, all the newly prepared products were tested for anti-inflammatory activity as analogues to fenamates, and some of them revealed moderate anti-inflammatory activity compared to the standard drug indomethacin.

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Brousseau, Danica, Jean-François Desjardins, Gaëtan Jasmin, and Louis Dumont. "Altered coronary and cardiac adrenergic response in the failing hamster heart: role of cyclooxygenase derivatives." Canadian Journal of Physiology and Pharmacology 80, no. 3 (2002): 218–25. http://dx.doi.org/10.1139/y02-042.

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Although the influence of the adrenergic system has been studied in the presence of heart failure, controversies still exist. Since cyclooxygenase derivatives appear to modulate coronary and cardiac adaptation in the failing heart, we hypothesized that cyclooxygenase derivatives may participate in the altered adrenergic responses in this situation. Isolated hearts from cardiomyopathic (UM-X7.1 subline) and normal hamsters, aged >240 days, were utilized. Coronary and cardiac response to α1-, β1-, and β2-adrenergic stimulations was observed before and after pretreatment with indomethacin, a cyclooxygenase inhibitor. Reduction of coronary flow elicited by α1-adrenergic stimulation was unchanged in the presence of heart failure, while β1- and β2-induced vasodilatations were reduced. Inotropic response to α1 and β1 stimulations were also reduced in failing hearts, while β2-adrenergic action was unchanged. Pretreatment with indomethacin exacerbated coronary flow reduction observed with α1 stimulation in failing hearts only. β2-induced coronary vasodilatation and inotropic response to α1 and β2 stimulations were impaired similarly in the presence of indomethacin in normal and failing hearts. The results suggest a complex interaction between adrenergic and cyclooxygenase activation.Key words: adrenergic, cyclooxygenase, heart failure, coronary flow, cardiac dynamics.

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Andreani, Aldo, Alberto Leoni, Alessandra Locatelli, et al. "Ring-Opened Analogs of Indomethacin Affecting Human Neutrophil Functions." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 299–312. http://dx.doi.org/10.1135/cccc19990299.

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A series of ring-opened analogs of indomethacin was synthesized and tested in vitro (at concentrations ranging from 10-9 to 10-5 mol/l) on human neutrophil functions. Two compounds lacking the carboxylic group were subjected to the same tests and one of these showed unexpected activity. Among the acidic derivatives, compound 12 bearing the same substituents as indomethacin 10 (methoxy and 4-chlorobenzoyl groups) was the most active: it significantly lowered neutrophil responses in all five bioassays and at the three concentrations considered.

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Kassab, Asmaa E., and Ehab M. Gedawy. "Repurposing of Indomethacin and Naproxen as anticancer agents: progress from 2017 to present." RSC Advances 14, no. 54 (2024): 40031–57. https://doi.org/10.1039/d4ra07581a.

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To aid in potential future repositioning of NSAIDs for cancer treatment, we summarize work from 2017–2024 on the antiproliferative activity of derivatives of indomethacin and naproxen, their mechanism of action and structure–activity relationships.

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Pop, Raluca, and Dušanka Janežič. "Interactions of Indomethacin with Functionalized Rhombellanes – a Molecular Docking Study." Croatica chemica acta 92, no. 4 (2020): 503–9. http://dx.doi.org/10.5562/cca3591.

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The specific properties of carbon-based nanomaterials like fullerenes and graphenes have attracted a continuous interest for their possible use as drug carriers. The functionalization of these nanomaterials can lead to the variation or improvement of the required properties, in order to lead to the design of the most suitable compounds within a specific field. In this regard, the possible use of a new class of nanostructures -the rhombellanes- as nanocarriers is investigated. The aim of the paper is to study the interactions of indomethacin and four analogues with anti-inflammatory activity on 13 rhombellanes (three of them with a hyper-adamantane motif, Ada-rbl, three cube-rhombellane homeomorphs, C-rbl, and seven cube-rhombellane-ether/amine structures). Five compounds with anti-inflammatory activity have been docked to the surface of the rhombellanes; comparisons with the results obtained for fullerene C60 have been performed. The best binding affinities for the indomethacin and its derivatives have been obtained for two types of rhombellanes, Ada-rbl and C-rbl. The indomethacin analogue I4 shows an increased binding affinity for C-rbl.420, similar to the value obtained for C60. Best results have been obtained for rhombellane derivatives characterized by smaller HOMO-LUMO gaps.

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OBATA, TOHRU, SARA SHIRATANI, TOMOMI NADA, et al. "Structure-activity Relationship of Indomethacin Derivatives as IDO1 Inhibitors." Anticancer Research 41, no. 5 (2021): 2287–96. http://dx.doi.org/10.21873/anticanres.15004.

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23

Moth, Christopher W., Jeffrey J. Prusakiewicz, Larry J. Marnett, and Terry P. Lybrand. "Stereoselective Binding of Indomethacin Ethanolamide Derivatives to Cyclooxygenase-1." Journal of Medicinal Chemistry 48, no. 10 (2005): 3613–20. http://dx.doi.org/10.1021/jm0494164.

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Tok, Fatih, and Bedia Koçyiğit-Kaymakçıoğlu. "Design, Synthesis and Biological Screening of Novel 1,5-Diphenyl-3-(4-(trifluoromethyl)phenyl)-2-pyrazoline Derivatives." Acta Chimica Slovenica 67, no. 4 (2020): 1139–47. http://dx.doi.org/10.17344/acsi.2020.6028.

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1-Phenyl-5-substituted-3-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazole derivatives were synthesized from chalcone derivatives. The structures of compounds were characterized by IR, 1H NMR spectroscopic methods and elemental analysis. All compounds were evaluated for their in vitro antioxidant activity using DPPH and ABTS methods, anti-inflammatory activity using lipoxygenase inhibitory method and antidiabetic activity using the α-glucosidase inhibitory method. Especially, pyrazoline derivatives exhibited stronger anti-inflammatory activity than the reference drug indomethacin (IC50: 50.45 μM) and their IC50 values were in the range of 0.68 and 4.45 μM. In addition, the ADME properties of all chalcone and pyrazoline derivatives were calculated by Lipinski’s and Veber’s rules.

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Hall, Iris H., Bruce S. Burnham, Shang Y. Chen, Anup Sood, Bernard F. Spielvogel, and Karen W. Morse. "The Anti-Inflammatory Activity of Boron Derivatives in Rodents." Metal-Based Drugs 2, no. 1 (1995): 1–12. http://dx.doi.org/10.1155/mbd.1995.1.

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Acyclic amine-carboxyboranes were effective anti-inflammatory agents in mice at 8 mg/kg x 2. These amine-carboxyboranes were more effective than the standard indomethacin at 8 mg/kg x 2, pentoxifylline at 50 mg/kg x 2, and phenylbutazone at 50 mg/kg x 2. The heterocyclic amine derivatives as well as amine-carbamoylboranes, carboalkoxyboranes, and cyanoboranes were generally less active. However, selected aminomethyl-phosphonate-N-cyanoboranes demonstrated greater than 60% reduction of induced inflammation. The boron compounds were also active in the rat induced edema, chronic arthritis, and pleurisy screens, demonstrating activity similar to the standard indomethacin. The compounds were effecive in reducing local pain and decreased the tail flick reflex to pain. The derivatives which demonstrated good anti-inflammatory activity were effective inhibitors of hydrolytic lysosomal, and proteolytic enzyme activities with IC50 values equal to 10-6M in mouse macrophages, human leukocytes, and Be Sal osteofibrolytic cells. In these same cell lines, the agents blocked prostaglandin cyclooxygenase activity with IC50 values of 10-6M. In mouse macrophage and human leukocytes, 5′ lipoxygenase activity was also inhibited by the boron derivatives with IC50 values of 10-6M. These IC50 values for inhibition of these enzyme activities are consistent with published values of known anti-inflammatory agents which target these enzymes.

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Mazzoni, MR, and A. Lucacchini. "Evidence for the Existence of A Specific Binding Site for Indomethacin on Bovine Vesicular Gland Microsomes." Biotechnology and Applied Biochemistry 9, no. 4 (1987): 339–45. http://dx.doi.org/10.1111/j.1470-8744.1987.tb00482.x.

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Using bovine vesicular gland microsomes and [14C]indomethacin we demonstrated the presence of a specific binding site for nonsteroidal anti‐inflammatory drugs. Specific binding of [14C]indomethacin to microsomes was rapid, with most of the ligand bound by 2 min at 4 degrees C. In routine binding assays the incubation temperature was maintained at 4 degrees C, because the maximal specific binding was obtained. Specific [14C]indomethacin binding appeared to increase linearly with increasing protein concentration over the range of 0.1‐1.0 mg of microsomal protein. Specific binding was saturable and Scatchard analysis of binding data showed a single class of binding sites with a dissociation constant (Kd) of 3.8 microM and a maximal number of binding sites (Bmax) of about 1272 pmol/mg of protein. When these binding data were plotted according to the Hill equation, a straight line was obtained with a Hill coefficient of 1.0. Structural specificity of the nonsteroidal anti‐inflammatory drug site was studied with diclofenac, arylpropionic acids (ketoprofen and indoprofen), and aspirin. Diclofenac and arylpropionic derivatives were able to compete with [14C]indomethacin for binding to microsomes, while aspirin was a weak inhibitor.

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El-Ossaily, Yasser A., Nuha M. M. Alanazi, Ibrahim O. Althobaiti, et al. "Multicomponent approach to the synthesis and spectral characterization of some 3,5-pyrazolididione derivatives and evaluation as anti-inflammatory agents." Current Chemistry Letters 13, no. 1 (2024): 127–40. http://dx.doi.org/10.5267/j.ccl.2023.8.003.

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Pyrazolones are a class of heterocyclic compounds that contain a pyrazole ring fused to a ketone group. Recent scientific research has focused extensively on the potential anti-inflammatory properties of pyrazolone compounds due to their diverse pharmacological effects in alleviating inflammation and reducing fever. This motivated us to focus on the preparation of these derivatives in a simple and eco-friendly manner. A convenient new green methodology was modified for the preparation of 1-phenyl-3,5-pyrazolidinedione by the sonicated MCR of diethyl malonate, phenylhydrazine, and a catalytic amount imidazole as homogenous organic catalyst in water green solvent in a good yield. On the other hand, some of 4-arylidinepyrazolidinedione derivatives are prepared in the same manner via the treatment of a mixture of diethyl malonate, phenylhydrazine, aromatic aldehydes, and a catalytic amount of imidazole in an aqueous medium. Our target synthesized pyrazolidinediones were elucidated via elemental and several spectral analyses. Due to the importance of pyrazolidinediones in the field of treating inflammation and relieving pain, a number of prepared compounds were chosen to test their efficacy as anti-inflammatory agents using carrageenan-induced foot edema in rats and compare the results with indomethacin, the standard drug. We found that the majority of derivatives yield promising results spanning from good to wonderful, so derivatives (15k, 15b, 15h, 15a, and 15j) yield the best results while derivative (15i) yields an average result. As for the derivative (15f), it yields the lowest results compared to the standard drug. This is due to the difference in the structural composition of these derivatives, which increases the likelihood of their use as anti-inflammatory derivatives.

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Wells, Isabelle, and Lawrence J. Marnett. "Inactivation of prostaglandin endoperoxide synthase by acylating derivatives of indomethacin." Biochemistry 32, no. 10 (1993): 2710–16. http://dx.doi.org/10.1021/bi00061a032.

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Chennamaneni, Snigdha, Chunfang Gan, Rati Lama, Bo Zhong, and Bin Su. "Indomethacin derivatives as tubulin stabilizers to inhibit cancer cell proliferation." Bioorganic & Medicinal Chemistry 24, no. 2 (2016): 277–85. http://dx.doi.org/10.1016/j.bmc.2015.12.016.

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Zhou, Yuxiang, Chenglong Li, Xiaoyan Yuan, Feiyan Zhang, Xiaozu Liu та Peijun Liu. "Cobalt-catalyzed C2α-acyloxylation of 2-substituted indoles with tert-butyl peresters". Organic & Biomolecular Chemistry 17, № 13 (2019): 3343–47. http://dx.doi.org/10.1039/c9ob00159j.

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An efficient cobalt-catalyzed C2α selective C(sp3)–H acyloxylation of 2-substituted indoles with tert-butyl peresters to synthesize diverse 2α-acyloxylated indole derivatives is described. This developed method exhibits mild conditions, low-cost catalyst, and high functional group compatibility. The effectiveness of this chemistry is illuminated by a late-stage modification of methylated indomethacin.

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Amrita, Dwivedi, and K. Srivastava A. "Modeling of inhibitory activity of indomethacin derivatives as COX-2 inhibitors through QSAR analysis." Journal of Indian Chemical Society 93, Jul 2016 (2016): 795–98. https://doi.org/10.5281/zenodo.5638006.

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QSAR Laboratory, Department of Chemistry, University of Allahabad, Allahabad-211 002, Uttar Pradesh, India E-mail : srivastavaak50@gmail.com Quantitative structure-activity relationships (QSAR) study has been performed on a series of indomethacin derivatives using topological and physicochemical parameters. Several QSAR equations were formulated through regression analysis by grouping these descriptors. It has been demonstrated that empirical parameters such as D, St, IOR along with indicator parameter have considerable effect on the inhibitory activity of these derivatives towards COX-2 enzyme. The best equation suggest is the tri-parametric model containing the parameters D, I1, I2 for modeling the activity of the compounds under present study and which was able to explain 81.3% of the variance in the data. The predictive ability of these equations was cross validated by evaluating the residual activity, cross validated R2 values (R2 CV) by leave one out (LOO) technique.

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Ermekova, Dinara, and Isabek Ismailov. "CONTENT-ANALYSIS OF THE PHARMACEUTICAL MARKET OF NONSTEROIDAL ANTI-INFLAMMATORY DRUGS IN GROUPS OF ACETIC ACID DERIVATIVES IN THE KYRGYZ REPUBLIC." Avicenna Bulletin 22, no. 1 (2020): 74–81. http://dx.doi.org/10.25005/2074-0581-2020-22-1-74-81.

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Objective: To segment the pharmaceutical market of non-steroidal anti-inflammatory drugs (NSAIDs) of the derivatives groups of acetic acid in the Kyrgyz Republic. Methods: The database of the State Registry of Medicines registered and approved for Medical use in Kyrgyzstan, the Department of Drugs Security and Medical Engineering of the Ministry of Health of the Kyrgyz Republic is used for analysis. Results: Analysis showed that the leaders of the pharmaceutical market in Kyrgyzstan the number of registered medicines (M) under the trade names are Medical Drugs (MD) with international generic name: diclofenac, ketorolac, indomethacin. It has been established that there are 99 trade names of NSAIDs of the groups of acetic acid derivatives in the Kyrgyz pharmaceutical market. The largest part of the range consists of diclofenac (M01AB05), represented by 62 trade names MD (62.6%), and ketorolac (M01AB15), represented by 20 trade names MD (20.2%). In the pharmaceutical market of Kyrgyzstan are NSAIDs from the groups of acetic acid derivatives from 15 countries, of which 21.1% of MDs are produced by neighboring countries, and 73.3% – in far countries. Conducted studies have revealed that the structure of the range of NSAIDs groups of acetic acid derivatives is dominated by soft medicinal forms, which making up 37.4%. A comparative analysis of the composition of MD by the number of active substances revealed that 92.9% of NSAIDs of the groups of acetic acid derivatives are monodrugs. Based on the analysis of the price segmentation of NSAIDs of the groups of acetic acid derivatives, most of the drugs are in the low-price segment. Conclusions: A sufficient assortment saturation of the pharmaceutical market of Kyrgyzstan NSAIDs groups of acetic acid derivatives has been revealed. The pharmaceutical market of the Kyrgyz Republic is dominated by monocomponent NSAIDs in the form of soft medicinal forms produced in foreign countries. Only 7 MDs from this group are in the high-price range, making the remaining drugs financially available to consumers. Keywords: NSAIDs, indomethacin, diclofenac, etodolac, ketorolac, aceclophenac.

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Xavier, Fabiano E., Javier Blanco-Rivero, Esther Sastre, Lina Badimón, and Gloria Balfagón. "Simultaneous inhibition of TXA2 and PGI2 synthesis increases NO release in mesenteric resistance arteries from cirrhotic rats." Clinical Science 119, no. 7 (2010): 283–92. http://dx.doi.org/10.1042/cs20090536.

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Our present study examines, in mesenteric resistance arteries, possible vasodilation alterations, and the role of NO and COX (cyclo-oxygenase) derivatives, in cirrhosis. The vasodilator response to acetylcholine was analysed in segments from control and cirrhotic rats. The effects of the non-specific COX inhibitor indomethacin, the specific COX-1 inhibitor SC-560 and the specific COX-2 inhibitor NS-398 were analysed in segments from both groups of rats. NO release was measured, and eNOS [endothelial NOS (NO synthase)], phospho-eNOS, iNOS (inducible NOS), COX-1 and COX-2 protein expression was also analysed. The effects of the TP receptor [TXA2 (thromboxane A2) receptor] antagonist SQ 29548, the TXA2 synthesis inhibitor furegrelate, the PGI2 (prostaglandin I2) synthesis inhibitor TCP (tranylcypromine) or TCP+furegrelate were only determined in segments from cirrhotic rats. The vasodilator response to acetylcholine was higher in segments from cirrhotic rats. Indomethacin, SC-560 and NS-398 did not modify the vasodilator response in control rats; however, indomethacin, NS-398 and TCP+furegrelate increased, whereas SC-560 did not modify and SQ 29548, furegrelate or TCP decreased, the vasodilator response to acetylcholine in cirrhotic rats. NO release was higher in cirrhotic rats. Furegrelate decreased, whereas TCP+furegrelate increased, the NO release in segments from cirrhotic rats. eNOS and COX-1 protein expression was not modified, whereas phosho-eNOS, iNOS and COX-2 protein expression was higher in cirrhotic rats. Therefore the increase in iNOS expression and eNOS activity may mediate increases in endothelial NO release. The COX-2 derivatives TXA2 and PGI2 may act simultaneously, producing a compensatory effect that reduces NO release and may limit the hyperdynamic circulation.

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Kant, Geeta, Anupama Parate, and SC Chaturvedi. "2D-QSAR study of indomethacin ester derivatives as cyclooxygenase-2- inhibitors." Indian Journal of Pharmaceutical Sciences 68, no. 6 (2006): 826. http://dx.doi.org/10.4103/0250-474x.31029.

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Amin, Mohamed M., Mohamed R. Shaaban, Nadia T. Al-Qurashi, Huda K. Mahmoud, and Thoraya A. Farghaly. "Indomethacin Analogs: Synthesis, Anti-inflammatory and Analgesic Activities of Indoline Derivatives." Mini-Reviews in Medicinal Chemistry 18, no. 16 (2018): 1409–21. http://dx.doi.org/10.2174/1389557518666180330101447.

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Zhang, Jiquan, Jianta Wang, Haoshu Wu, et al. "Design, synthesis and insulin-sensitizing activity of indomethacin and diclofenac derivatives." Bioorganic & Medicinal Chemistry Letters 19, no. 12 (2009): 3324–27. http://dx.doi.org/10.1016/j.bmcl.2009.04.050.

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Scholz, Matthias, Anna L. Blobaum, Lawrence J. Marnett, and Evamarie Hey-Hawkins. "Synthesis and evaluation of carbaborane derivatives of indomethacin as cyclooxygenase inhibitors." Bioorganic & Medicinal Chemistry 19, no. 10 (2011): 3242–48. http://dx.doi.org/10.1016/j.bmc.2011.03.054.

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Scholz, Matthias, Anna L. Blobaum, Lawrence J. Marnett, and Evamarie Hey-Hawkins. "ortho-Carbaborane derivatives of indomethacin as cyclooxygenase (COX)-2 selective inhibitors." Bioorganic & Medicinal Chemistry 20, no. 15 (2012): 4830–37. http://dx.doi.org/10.1016/j.bmc.2012.05.063.

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Amir, Mohd, and Shikha Kumar. "Anti-inflammatory and Gastro Sparing Activity of Some New Indomethacin Derivatives." Archiv der Pharmazie 338, no. 1 (2005): 24–31. http://dx.doi.org/10.1002/ardp.200400891.

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Camacho-Camacho, Carlos, Irma Rojas-Oviedo, M. Angeles Paz-Sandoval, et al. "Synthesis, structural characterization and cytotoxic activity of organotin derivatives of indomethacin." Applied Organometallic Chemistry 22, no. 3 (2008): 171–76. http://dx.doi.org/10.1002/aoc.1366.

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Bafail, Rawan S. M., and Waad A. Samman. "Anti-parkinsonian, anti-inflammatory, anti-microbial, analgesic, anti-hyperglycemic and anticancer activities of poly-fused ring pyrimidine derivatives." Tropical Journal of Pharmaceutical Research 23, no. 1 (2024): 67–75. http://dx.doi.org/10.4314/tjpr.v23i1.9.

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Purpose: To investigate the anti-inflammatory, anti-cancer, anti-parkinsonian, anti-microbial, analgesic, and anti-hyperglycemic properties of a variety of poly-fused pyrimidine derivatives. Methods: A novel series of fused pyrimidine derivatives 1-6 were synthesized by reacting amino pyrazole derivatives with active methylene derivatives to give the corresponding compounds 1-6. Anti-parkinsonian activity was investigated with benzotropene as a reference drug, anti-inflammatory effect in mice was evaluated using carrageenan in paw edema with indomethacin as reference drug, anti-microbial activity was assessed using nutritional agar with ciprofloxacin and ketoconazole as reference drugs, analgesic activity was evaluated using valdecoxib as reference drug, anti-hyperglycemic activity was investigated using alloxan and sucrose models (SLM) with pioglitazone as reference drug and anticancer activity was investigated using the MTT micro-cultured tetrazolium assay method with doxorubicin as reference drug. Results: Pyrimidine derivatives 1-6 possess significant active anti-parkinsonian, anti-inflammatory, anti-microbial, analgesic, anti-hyperglycemic and anticancer activities in comparison to the reference drugs used for each model. Compared to Benzotropene®, compounds 1 and 3 showed a significantly stronger anti-parkinsonian activity (p < 0.03). Compound 3 showed a significantly stronger anti-inflammatory effect than Indomethacin® (p < 0.05). Compounds 5 and 6 exhibited significant anti- microbial activity compared to ciprofloxacin® (p < 0.05). Compounds 4 and 6 exhibited significantly improved analgesic activity as compared to Valdecoxib® (p < 0.01). Compounds 1 and 3 exhibited significantly higher anti-hyperglycemic effects in SLM model when compared to pioglitazone® (p < 0.02). Compound 5 demonstrated the highest activity against human colon cancer cell line (HT-29) and human prostate cancer cell line (DU145), and also, significantly improved level of efficacy against human lung cancer cell line (A549) compared to Doxorubicin® (p < 0.02).  Conclusion: Using the six pyrimidine derivatives 1 - 6 as a lead molecule, a novel class of clinically beneficial anti-cancer, anti-inflammatory, anti-microbial, analgesic, and anti-hyperglycemic drugs may be produced.

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Lee, Bong-Seop, Xiangpeng Yuan, Qijin Xu, et al. "Nanoprodrugs of NSAIDs Inhibit the Growth of U87-MG Glioma Cells." Journal of Nanomaterials 2010 (2010): 1–10. http://dx.doi.org/10.1155/2010/583970.

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Several recent reports have demonstrated that nonsteroidal anti-inflammatory drugs (NSAIDs) inhibit the growth of various malignant cells suggesting their application as anticancer agents. In this study, we prepared six nanometer-sized prodrugs (nanoprodrugs) of NSAIDs, ibuprofen, indomethacin, and naproxen through the spontaneous emulsification mechanism using monomeric and dimeric derivatives of the NSAIDs. We evaluated their effect on the proliferation of U87-MG glioma cells by cell counting, WST-1 cell proliferation reagent, and propidium iodide incorporation. The two ibuprofen nanoprodrugs inhibited the cell growth more potently than the indomethacin nanoprodrugs, whereas the naproxen nanoprodrugs did not show any significant effect. Remarkably, ibuprofen did not show any effect at an equimolar concentration. Approximately, 4.4% of the ibuprofen nanoprodrugs was found in the cell, whereas no ibuprofen could be detected suggesting that the superior effect of the nanoprodrugs can be attributed to the efficient cellular uptake of the nanoprodrugs.

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Menshawy, A. Mohamed* Adnan A. Beckeit Adel S. El-Azab Ghada F. Mohamed Sami G. Abdel-Hamid and Maged S. Abdel-Kader. "SYNTHESIS AND EVALUATION OF SOME UMBELLIFERONE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS." INDO AMERICAN JOURNAL OF PHARMACEUTICAL SCIENCES 05, no. 12 (2018): 16165–77. https://doi.org/10.5281/zenodo.2268635.

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Seventeen 7-hydroxy coumarin (umbelliferone) derivatives were synthesized in an almost quantitative yield via reaction with the corresponding ethylchloroacetate, p-substituted benzyl chloride, 2-bromoacetophenone or 2-chloroacetanilide in the presence of anhydrous potassium carbonate in dry acetone.  The compounds were tested for their anti-inflammatory activity using cotton pellet implantation test and carrageenan-induced rat paw edema. The ulcerogenic effect of the compounds was also studied comparing with the NSAID indomethacin. Keywords : 7-Hydroxy coumarin (umbelliferone); synthesis; anti-inflammatory; ulcerogenic effects.

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Stadlbauer, Sven, René Frank, Matthias Scholz, et al. "Imitation and modification of bioactive lead structures via integration of boron clusters." Pure and Applied Chemistry 84, no. 11 (2012): 2289–98. http://dx.doi.org/10.1351/pac-con-11-11-02.

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In medicinal chemistry, carbaboranes can be employed either as boron carriers for boron neutron capture therapy (BNCT) or as scaffolds for radiodiagnostic or therapeutic agents. We have developed a suitable synthesis employing the phosphoramidite method to connect meta-carbaboranyl bis-phosphonites with the 6'-OH group of isopropylidene-protected galactose, followed by oxidation or sulfurization to give the corresponding bis-phosphonates. Deprotection yielded water-soluble compounds. The corresponding disodium salts exhibit especially low cytotoxicity. Preliminary results on the in vivo toxicity and biodistribution of two compounds in mice indicated a lack of selectivity for the cotton rat lung (CRL) tumor chosen for the experiment. For the incorporation of carbaboranes into breast tumor-selective modified neuropeptide Y, [F7, P34]-NPY, a synthesis of a carbaborane-modified lysine derivative was developed. Linkage of the lysine to the boron cluster was achieved by using a propionic acid spacer. Incorporation of the amino acid derivatives into NPY and [F7, P34]-NPY by solid-phase peptide synthesis was successful. Preliminary studies showed that the receptor binding affinity and signal transduction of the boron-modified peptides were very well retained. Asborin, the carbaborane analogue of aspirin, is a rather weak inhibitor of cyclooxygenase-1 (COX-1) and COX-2, but a highly potent aldo/keto reductase 1A1 (AKR1A1) inhibitor. Modification either at the carboxyl group or at the chlorophenyl ring in indomethacin with ortho- and meta-carbaboranyl derivatives gave active derivatives only for the ortho-carbaborane directly attached to the carboxyl group, while the corresponding adamantyl and meta-carbaboranyl derivatives were inactive.

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Felts, Andrew S., Chuan Ji, Jennifer B. Stafford, et al. "Desmethyl Derivatives of Indomethacin and Sulindac as Probes for Cyclooxygenase-Dependent Biology." ACS Chemical Biology 2, no. 7 (2007): 479–83. http://dx.doi.org/10.1021/cb700077z.

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De Caprariis, Paolo, Francesco Palagiano, Franco Bonina, Lucia Montenegro, Michele D'Amico, and Francesco Rossi. "Synthesis and Pharmacological Evaluation of Oligoethylene Ester Derivatives as Indomethacin Oral Prodrugs." Journal of Pharmaceutical Sciences 83, no. 11 (1994): 1578–81. http://dx.doi.org/10.1002/jps.2600831112.

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Hegab, Mohamed, Nabil Yousef, Hany Nour, Mohey Ellithey, and Mahmoud Arbid. "Synthesis and pharmacological activities of some condensed 4-chloro-2,2-dialkyl chromene-3-carbaldehyde derivatives." Acta Pharmaceutica 58, no. 1 (2008): 15–27. http://dx.doi.org/10.2478/v10007-007-0042-4.

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Synthesis and pharmacological activities of some condensed 4-chloro-2,2-dialkyl chromene-3-carbaldehyde derivativesSome new hydrazono5a,b, thiosemicarbazono6a-c, and oximo chromenes7a-cwere preparedviathe reaction of the corresponding β-chlorocarbaldehyde3with hydrazine, aromatic hydrazine, thiosemicarbazide and hydroxylamine hydrochloride, respectively. In addition, ether derivatives8a-hwere prepared from the corresponding aldoximes7a-c. The new products were tested for anti-inflammatory and ulcerogenic score activities compared to indomethacin.

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Knight, John, Andrew F. Rowley, Mizue Yamazaki, and Anthony S. Clare. "Eicosanoids are modulators of larval settlement in the barnacle, Balanus amphitrite." Journal of the Marine Biological Association of the United Kingdom 80, no. 1 (1999): 113–17. http://dx.doi.org/10.1017/s0025315499001629.

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Eicosanoids are oxygenated derivatives of C20 polyunsaturated fatty acids known to play key roles in many physiological events in both invertebrates and vertebrates. The eicosanoid generating capacity of cypris larvae of the barnacle, Balanus amphitrite, was examined using enzyme immunoassay and high-performance liquid chromatography. These larvae generated the lipoxygenase products, 12-hydroxyeicosapentaenoic acid (HEPE), 8-HEPE and 8,15-diHEPE, together with the cyclooxygenase products, prostaglandin (PG) E, PGF and thromboxane (TX) B. Indomethacin, a selective cyclooxygenase inhibitor, caused a dose-dependent inhibition of PGE generation by B. amphitrite larvae, while esculetin and nordihydroguaiaretic acid (lipoxygenase inhibitors) also strongly inhibited the generation of 8-HEPE, 12-HEPE and 8,15-diHEPE. PGE2, PGE3 and 16,16-dimethyl PGE2 caused a dose-dependent inhibition of settlement of B. amphitrite larvae while indomethacin (25–100 μM) stimulated this process. Lipoxygenase products (8-HEPE, 12-HEPE and 8,15-diHEPE) as well as esculetin and nordihydroguaiaretic acid (10–100 μM) had no effect on the attachment of larvae.

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Venugopala, Katharigatta N., Sandeep Chandrashekharappa, Christophe Tratrat, et al. "Crystallography, Molecular Modeling, and COX-2 Inhibition Studies on Indolizine Derivatives." Molecules 26, no. 12 (2021): 3550. http://dx.doi.org/10.3390/molecules26123550.

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The cyclooxygenase-2 (COX-2) enzyme is an important target for drug discovery and development of novel anti-inflammatory agents. Selective COX-2 inhibitors have the advantage of reduced side-effects, which result from COX-1 inhibition that is usually observed with nonselective COX inhibitors. In this study, the design and synthesis of a new series of 7-methoxy indolizines as bioisostere indomethacin analogues (5a–e) were carried out and evaluated for COX-2 enzyme inhibition. All the compounds showed activity in micromolar ranges, and the compound diethyl 3-(4-cyanobenzoyl)-7-methoxyindolizine-1,2-dicarboxylate (5a) emerged as a promising COX-2 inhibitor with an IC50 of 5.84 µM, as compared to indomethacin (IC50 = 6.84 µM). The molecular modeling study of indolizines indicated that hydrophobic interactions were the major contribution to COX-2 inhibition. The title compound diethyl 3-(4-bromobenzoyl)-7-methoxyindolizine-1,2-dicarboxylate (5c) was subjected for single-crystal X-ray studies, Hirshfeld surface analysis, and energy framework calculations. The X-ray diffraction analysis showed that the molecule (5c) crystallizes in the monoclinic crystal system with space group P 21/n with a = 12.0497(6)Å, b = 17.8324(10)Å, c = 19.6052(11)Å, α = 90.000°, β = 100.372(1)°, γ = 90.000°, and V = 4143.8(4)Å3. In addition, with the help of Crystal Explorer software program using the B3LYP/6-31G(d, p) basis set, the theoretical calculation of the interaction and graphical representation of energy value was measured in the form of the energy framework in terms of coulombic, dispersion, and total energy.

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Narożna, Maria, Violetta Krajka-Kuźniak, Robert Kleszcz, and Wanda Baer-Dubowska. "Indomethacin and Diclofenac Hybrids with Oleanolic Acid Oximes Modulate Key Signaling Pathways in Pancreatic Cancer Cells." International Journal of Molecular Sciences 23, no. 3 (2022): 1230. http://dx.doi.org/10.3390/ijms23031230.

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Our earlier studies showed that coupling nonsteroidal anti-inflammatory drugs (NSAIDs) with oleanolic acid derivatives increased their anti-inflammatory activity in human hepatoma cells. The aim of this study was to evaluate their effect on the signaling pathways involved in inflammation processes in human pancreatic cancer (PC) cells. Cultured PSN-1 cells were exposed for 24 h (30 µM) to OA oxime (OAO) derivatives substituted with benzyl or morpholide groups and their conjugates with indomethacin (IND) or diclofenac (DCL). The activation of NF-κB and Nrf2 was assessed by the evaluation of the translocation of their active forms into the nucleus and their binding to specific DNA sequences via the ELISA assay. The expression of NF-κB and Nrf2 target genes was evaluated by R-T PCR and Western blot analysis. The conjugation of IND or DCL with OAO derivatives increased cytotoxicity and their effect on the tested signaling pathways. The most effective compound was the DCL hybrid with OAO morpholide (4d). This compound significantly reduced the activation and expression of NF-κB and enhanced the activation and expression of Nrf2. Increased expression of Nrf2 target genes led to reduced ROS production. Moreover, MAPKs and the related pathways were also affected. Therefore, conjugate 4d deserves more comprehensive studies as a potential PC therapeutic agent.

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Journal articles on the topic 'Indomethacin derivatives'

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