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Journal articles on the topic 'Amide derivatives of N-benzyl-3-aminotropane'
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Jílek, Jiří, Miroslav Rajšner, Vladimír Valenta, Miloš Borovička, Jiří Holubek, Miroslav Ryska, Emil Svátek, Jan Metyš, and Miroslav Protiva. "Synthesis of piperidine derivatives as potential analgetic agents." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1828–53. http://dx.doi.org/10.1135/cccc19901828.
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Reaction of N-(1-(2-phenylethyl)-4-piperidinyl)propionanilide (I) with phosphorus pentasulfide gave the thioamide VI. Acylation of N-(1-(2-phenylethyl)-4-piperidinyl)aniline with 2-(methoxy)acetic and 2-(methylthio)acetic anhydrides afforded the amides II and III. Treatment of 4-anilino-1-benzylpiperidine-4-methanol with thionyl chloride gave the spirocyclic sulfurous acid ester amide XIV. Reduction of the hydrochloride of ethyl 3-(1-ethoxycarbonyl-4-phenylimino-3-piperidinyl)propionate (XXII) with sodium cyanoborohydride gave the perhydro-1,6-naphthyridine derivative XIX, a model compound in the synthesis of the cyclic analogue of fentanyl (I). Ethyl 4-anilino-1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-3-carboxylate (XXIX) hydrochloride, obtained by reaction of ethyl 4-oxo-1-(2-phenylethyl)piperidine-3-carboxylate hydrochloride with aniline, was reduced with lithium aluminium hydride to 4-anilino-1-(2-phenylethyl)piperidine-3-methanol (XXXI). 1-Methyl- and 1-benzyl-4-piperidone were reacted with 4-cyclopropylphenylmagnesium bromide and the tertiary alcohols XXXVII and XXXVIII obtained were acylated with propionyl chloride to give the esters XXXIX and XL. The piperidine derivatives XLI, XLVI and XLVIII were prepared as potential neurotropic agents. Alkylation of 8-hydroxy-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (XLIX) with 2-(2-chloroethyl)-1,3-dioxane and -1,3-dioxolane resulted in the 6,7-benzomorphan derivatives L and LI. Out of the compounds prepared, only the closest fentanyl analogues II, III, and VI showed very strong analgetic activity.
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Valenta, Vladimír, Zdeněk Vejdělek, Karel Šindelář, and Miroslav Protiva. "Potential anticonvulsants: Some derivatives and analogues of 2-propylpentanoic acid." Collection of Czechoslovak Chemical Communications 55, no. 4 (1990): 1067–76. http://dx.doi.org/10.1135/cccc19901067.
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Reaction of 2-(ethoxycarbonylamino)ethanol with 2-propylpentanoyl chloride gave the ester III. N-(4-Piperidinyl)-2-propylpentanamide (V) was prepared via the 1-benzyl-4-piperidinyl derivative IV and was acylated with ethanesulfonyl chloride and 2-propylpentanoyl chloride to give the amides VI and VII. Malonic ester syntheses afforded diethyl 2-ethyl- and 2-propyl-2-(2-(methylthio)ethyl)malonate VIII and XIII which were hydrolyzed and decarboxylated to the acids X and XV which, in turn, were transformed to the amides XII and XVII. 3-Thiapentanenitrile was alkylated with propyl bromide to the nitrile XIX which was hydrolyzed to the acid XX and the amide XXI. The acids X, XV, and XX, and the amides XII, XVII, and XXI are analogues of the anticonvulsant agents valproic acid (I) and valpromide (II). Compounds XX (V⁄FB-14 721) and XXI (V⁄FB-14 722) potentiate, in doses in which they ìper seî are ineffective as anticonvulsants in mice, significantly the anticonvulsant effect of diazepam.
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Ravikumar, Krishnan, Balasubramanian Sridhar, Jagadeesh Babu Nanubolu, Tamilselvan Rajasekaran, and Basi Venkata Subba Reddy. "Four oxoindole-linked α-alkoxy-β-amino acid derivatives." Acta Crystallographica Section C Structural Chemistry 71, no. 4 (March 21, 2015): 322–29. http://dx.doi.org/10.1107/s2053229615005604.
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Four structures of oxoindolyl α-hydroxy-β-amino acid derivatives, namely, methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-methoxy-2-phenylacetate, C24H28N2O6, (I), methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-ethoxy-2-phenylacetate, C25H30N2O6, (II), methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-[(4-methoxybenzyl)oxy]-2-phenylacetate, C31H34N2O7, (III), and methyl 2-[(anthracen-9-yl)methoxy]-2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-phenylacetate, C38H36N2O6, (IV), have been determined. The diastereoselectivity of the chemical reaction involving α-diazoesters and isatin imines in the presence of benzyl alcohol is confirmed through the relative configuration of the two stereogenic centres. In esters (I) and (III), the amide group adopts ananticonformation, whereas the conformation issynin esters (II) and (IV). Nevertheless, the amide group forms intramolecular N—H...O hydrogen bonds with the ester and ether O atoms in all four structures. The ether-linked substituents are in the extended conformation in all four structures. Ester (II) is dominated by intermolecular N—H...O hydrogen-bond interactions. In contrast, the remaining three structures are sustained by C—H...O hydrogen-bond interactions.
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Gomes, Ligia R., John Nicolson Low, Catarina Oliveira, Fernando Cagide, and Fernanda Borges. "Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives." Acta Crystallographica Section E Crystallographic Communications 72, no. 5 (April 15, 2016): 675–82. http://dx.doi.org/10.1107/s2056989016005958.
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The crystal structures of three benzamide derivatives,viz. N-(6-hydroxyhexyl)-3,4,5-trimethoxybenzamide, C16H25NO5, (1),N-(6-anilinohexyl)-3,4,5-trimethoxybenzamide, C22H30N2O4, (2), andN-(6,6-diethoxyhexyl)-3,4,5-trimethoxybenzamide, C20H33NO6, (3), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the molecules. In each molecule, them-methoxy substituents are virtually coplanar with the benzyl ring, while thep-methoxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer istransrelated with the amidic H atom. In each structure, the benzamide N—H donor group and O acceptor atoms link the molecules intoC(4) chains. In1, a terminal –OH group links the molecules into aC(3) chain and the combined effect of theC(4) andC(3) chains is a ribbon made up of screw relatedR22(17) rings in which the ...O—H... chain lies in the centre of the ribbon and the trimethoxybenzyl groups forms the edges. In2, the combination of the benzamideC(4) chain and the hydrogen bond formed by the terminal N—H group to an O atom of the 4-methoxy group link the molecules into a chain ofR22(17) rings. In3, the molecules are linked only byC(4) chains.
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Romanenko, M. I., D. G. Ivanchenko, T. A. Sharapova, I. M. Bilay, and K. V. Aleksandrova. "Synthesis and hypoglycemic activity of 7-n-butyl-3-methyl-8-thioxanthine derivatives." Farmatsevtychnyi zhurnal, no. 6 (August 14, 2018): 95–104. http://dx.doi.org/10.32352/0367-3057.6.16.07.
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According to the International Diabetes Federation in 2015 were registered 59.8 million patients with diabetes in Europe. Synthetic drugs are widely applied in addition to a variety of insulins to normalize blood glucose level. It should be noted that the oral anti-diabetic drugs are the common therapeutic agents for the treatment of diabetes mellitus type II, and therefore the search for new non-toxic hypoglycemic agents is one of the most urgent problems of modern pharmaceutical science. It is known that 7,8-disubstituted xanthine derivatives exhibit hypoglycemic activity.
The aim of this work lies in developing unique method to synthesize undocumented in other scientific papers 7-n-butyl-3-methyl-8-thioxanthine derivatives and also studying of their hypoglycemic activity.
Acute toxicity of synthesized compounds has been studied with the application of Prozorovsky’s method. The glucose homeostasis characteristic has been performed on carbohydrate tolerance that has been determined by the glucose load test on the control group and on the intact rats.
The reactions of 7-n-butyl-3-methyl-8-thioxanthine with benzylchlorides, bromoketones, esters and an amide of chloroacetic acid have been studied. Reactions of mentioned syntons proceed smoothly in aqueous propanol-2 environment and lead to the formation of the corresponding 8-benzyl-, benzoylmethylthioxanthines and xanthinyl-8-thioacetic acid derivatives.
Accessible laboratory method has been elaborated to synthesize unspecified in scientific papers earlier 8-thiosubstituted 7-n-butyl-3-methylxanthine by reacting 7-n-butyl-3-methyl-8-thioxanthine with benzylchlorides, bromoketones, esters and an amide of chloroacetic acid, their structure having been proved by NMR-spectroscopy data. The acute toxicity of synthesized compounds has been studied. It has been established that LD50 is in the range 820–2477 mg/kg, i. e. obtained substances are low-toxic and practically non-toxic according to Sidorov’s classification. Also the study of hypoglycemic activity of synthesized compounds has been carried out. A significant perspective for further research to find the original antidiabetic agents has been shown by bioassay results. It has been found that 7-n-butyl-3-methylxanthinyl-8-thioacetamide is more active than reference substances.
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Prabu, D. Sam Daniel, Sivalingam Lakshmanan, K. Thirumurugan, N. Ramalakshmi, and S. Arul Antony. "Synthesis, Molecular Docking, DFT Study of Novel N-Benzyl-2-(3-cyano-4-isobutoxyphenyl)- 4-methylthiazole-5-carboxamide Derivatives and their Antibacterial Activity." Asian Journal of Chemistry 32, no. 3 (January 31, 2020): 619–26. http://dx.doi.org/10.14233/ajchem.2020.22390.
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A series of febuxostat based new chemical entities was synthesized using microwave method and characterized by NMR, mass and FT-IR spectral studies. Molecular docking of febuxostat amide nucleus substitution compounds 8c (-7.91kcal/mol), 8g (-7.94 kcal/mol) exhibiting high binding energy against ALK receptors. Theoretical investigation of MEPs, HOMO, LUMO and energy gap of HOMO-LUMO were calculated by B3LYP/6-31G method. Among the tested compounds, methoxy substituted compound 8g showed highest antibacterial activity against S. aereus and B. subtilis.
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Jones, R., A. G. M. Rattray, S. J. Rettig, J. R. Scheffer, and J. Trotter. "Structures and photochemistry of dibenzobarrelene monoamides." Acta Crystallographica Section B Structural Science 52, no. 6 (December 1, 1996): 1007–13. http://dx.doi.org/10.1107/s0108768196009056.
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The photochemistry of 9,10-ethenoanthracene-11-monoamides has been studied and correlated with the crystal structures determined for two derivatives; photoproduct structures have been established from a crystal structure analysis of one of the products and from NMR correlations. Crystal data are: (1)-Et, N, N-diethyl-9,10-dihydro-9,10-ethenoanthracene-11-carboxamide, C21H21NO, Pbca; (1)-Pr, 9,10-dihydro-N,N-di(isopropyl)-9,10-ethenoanthracene-11-carboxamide, C23H25NO, P21/c; (2 L)-Bz, 9,10-dihydro-9,10-ethenoanthracene-11-spiro-3′-(1-benzyl-4-phenylazetidine)-2′-one, C31H25NO (+ solvent), P21/a (Z = 8). The two dibenzobarrelene molecules have geometries and dimensions similar to those of related materials; the amide group in each molecule is only partially conjugated with the C 11=C 12 double bond. Mechanisms are derived for the formation of three types of photoproduct: (i) the well known di-π-methane reaction [(2M)-type photoproduct]; (ii) a hydrogen abstraction process (2H); (iii) β-lactam formation (2 L).
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Culletta, Giulia, Maria Zappalà, Roberta Ettari, Anna Maria Almerico, and Marco Tutone. "Immunoproteasome and Non-Covalent Inhibition: Exploration by Advanced Molecular Dynamics and Docking Methods." Molecules 26, no. 13 (July 2, 2021): 4046. http://dx.doi.org/10.3390/molecules26134046.
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The selective inhibition of immunoproteasome is a valuable strategy to treat autoimmune, inflammatory diseases, and hematologic malignancies. Recently, a new series of amide derivatives as non-covalent inhibitors of the β1i subunit with Ki values in the low/submicromolar ranges have been identified. Here, we investigated the binding mechanism of the most potent and selective inhibitor, N-benzyl-2-(2-oxopyridin-1(2H)-yl)propanamide (1), to elucidate the steps from the ligand entrance into the binding pocket to the ligand-induced conformational changes. We carried out a total of 400 ns of MD-binding analyses, followed by 200 ns of plain MD. The trajectories clustering allowed identifying three representative poses evidencing new key interactions with Phe31 and Lys33 together in a flipped orientation of a representative pose. Further, Binding Pose MetaDynamics (BPMD) studies were performed to evaluate the binding stability, comparing 1 with four other inhibitors of the β1i subunit: N-benzyl-2-(2-oxopyridin-1(2H)-yl)acetamide (2), N-cyclohexyl-3-(2-oxopyridin-1(2H)-yl)propenamide (3), N-butyl-3-(2-oxopyridin-1(2H)-yl)propanamide (4), and (S)-2-(2-oxopyridin-1(2H)-yl)-N,4-diphenylbutanamide (5). The obtained results in terms of free binding energy were consistent with the experimental values of inhibition, confirming 1 as a lead compound of this series. The adopted methods provided a full dynamic description of the binding events, and the information obtained could be exploited for the rational design of new and more active inhibitors.
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El Kayal, Wassim, Hanna Severina, Vadim Tsyvunin, Sergiy Zalevskyi, Sergiy Shtrygol’, Sergiy Vlasov, Olga Golovchenko, Sergiy Kovalenko, and Victoriya Georgiyants. "Synthesis and anticonvulsant activity evaluation of n-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1h-quinazolin-3-yl)acetamide novel 1-benzylsubstituted derivatives." ScienceRise: Pharmaceutical Science, no. 1(35) (February 28, 2022): 58–69. http://dx.doi.org/10.15587/2519-4852.2022.253554.
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The aim. Synthesis of 1-benzylsubstituted derivatives of N-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1h-quinazolin-3-yl)acetamide, and determination of affinity to GABAergic biotargets with the following anticonvulsant activity estimation using PTZ-induced seizures model in mice.
Materials and methods. Standard organic synthesis methods were used; the structure of the synthesized compounds was proved by elemental analysis, 1H and 13C NMR spectroscopy, and LC/MS method; composition of the synthesized compounds – by elemental analysis, their individuality – by TLC and LC/MS methods. AutoDockTools-1.5.6, as well as AutoDock Vina software, was used to perform molecular docking. Anticonvulsant activity was studied using pentylenetetrazole-induced seizures in mice.
Results. A targeted N-[(2,4-dichlorophenyl)methyl]-2-(1-(R-benzyl)-2,4-dioxo-quinazolin-3-yl)acetamides were obtained by alkylation of N-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1H-quinazolin-3-yl)acetamide by corresponding 1-chloromethylbenzene in dimethylformamide environment with excess of potassium carbonate at a temperature 70-80 ˚С. Prediction of activity of 1-benzyl derivatives in the pentylenetetrazole-induced seizures in an in vivo experiment was carried out according to the obtained results of docking studies – affinity calculation for GABA receptor and GABA enzyme active sites, as well as analysis of conformational placement in them. In relation to the binding energy, the studied ligands were inferior to the reference drugs: GABA receptor positive allosteric modulators – benzamidine and diazepam, and GABA inhibitor – vigabatrin. The synthesized substances did not show anticonvulsant activity: only 2 compounds have shown a tendency to their activity manifestation according to the criterion of integral protective indicator – reduction of mortality by 17 % compared to control, as well as prolonging the time death of the animals. Comparison with the preliminary obtained results of the activity of the promising anticonvulsant N-[(2,4-dichlorophenyl)methyl] -2-(2,4-dioxo-1H-quinazolin-3-yl) acetamide N-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1H-quinazolin-3-yl)acetamide made possible to prove the pharmacophore role of the cyclic amide fragment in anticonvulsant activity manifestation.
Conclusion. The synthesis of N-[(2,4-dichlorophenyl)methyl]-2-(1-(R-benzyl)-2,4-dioxo-quinazolin-3-yl)acetamides, which have not still described in the literature, was carried out, as well as the structure of the mentioned compounds was proved. Unfortunately, the substances did not show anticonvulsant activity on the model of pentylenetetrazole-induced seizures. However, the obtained results allowed establishing the key role of the NHCO cyclic fragment on anticonvulsant activity. A positive correlation between the results of in vivo studies and in silico calculations was found – the model of pentylenetetrazole-induced seizures and docking into the active sites of PAMs GABAА receptor and enzyme inhibitor GABAАТ, which allows to recommend the given docking methodology as a tool to streamline and optimize the screening on the mentioned model
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Li, Wen, Shu-Yi Chen, Wei-Nan Hu, Mei Zhu, Jia-Min Liu, Yi-Hong Fu, Zhen-Chao Wang, and Gui-Ping OuYang. "Design, synthesis, and biological evaluation of quinazoline derivatives containing piperazine moieties as antitumor agents." Journal of Chemical Research 44, no. 9-10 (March 17, 2020): 536–42. http://dx.doi.org/10.1177/1747519820910384.
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A series of novel quinazoline derivatives containing piperazine analogs are synthesized via substitution reactions with 6,7-disubstituted 4-chloroquinazoline and benzyl piperazine (amido piperazine). Potent antiproliferative activities are observed against A549, HepG2, K562, and PC-3 with N-(3-chlorophenyl)-2-(4-(7-methoxy-6-(3-morpholino-propoxy)quinazoline-4-yl)piperazine-1-yl)acetamidename C9 showing excellent activity. This active derivative was screened for cell migration ability, proliferation effects, and apoptosis against A549 and PC-3 cells, with the result showing biological activity almost equal to that of the control gefitinib.
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Mahjub, Reza, Farzane K. Najafabadi, Narges Dehkhodaei, Nejat Kheiripour, Amir N. Ahmadabadi, Sara S. Asl, Masomeh Taheri-Azandariani, and Akram Ranjbar. "Eudragit L-100 Capsules Aromatize and Quaternerize Chitosan for Insulin Nanoparticle Oral Delivery During Toxic Oxidative Stress in Rat Liver and Kidney." Pharmaceutical Nanotechnology 8, no. 3 (September 30, 2020): 239–54. http://dx.doi.org/10.2174/2211738508666200628033442.
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Background: Insulin, like most peptides, is classified as a hydrophilic and macromolecular drug that is considered as a low permeable and unstable compound in the gastrointestinal (GI) tract. The acidic condition of the stomach can degrade insulin molecules. Moreover, the presence of proteolytic activities of some enzymes such as trypsin and chymotrypsin can hydrolyze amide-bonds between various amino-acids in the structures of peptides and proteins. However, due to its simplicity and high patient compliance, oral administration is the most preferred route of systemic drug delivery, and for the development of an oral delivery system, some obstacles in oral administration of peptides and proteins including low permeability and low stability of the proteins in GI should be overcome. Objective: In this study, the effects of orally insulin nanoparticles (INPs) prepared from quaternerized N-aryl derivatives of chitosan on the biochemical factors of the liver in diabetic rats were studied. Methods: INPs composed of methylated (amino benzyl) chitosan were prepared by the PEC method. Lyophilized INPs were filled in pre-clinical capsules, and the capsules were enteric-coated with Eudragit L100. Twenty Male Wistar rats were randomly divided into four groups: group1: normal control rats, group 2: diabetic rats, group 3: diabetic rats received capsules INPs(30 U/kg/day, orally), group 4: the diabetic rats received regular insulin (5 U/kg/day, subcutaneously). At the end of the treatment, serum, liver and kidney tissues were collected. Biochemical parameters in serum were measured using spectrophotometric methods. Also, oxidative stress was measured in plasma, liver and kidney. Histological studies were performed using H and E staining . Results: Biochemical parameters, and liver and kidney injury markers in serum of the diabetic rats that received INPs improved significantly compared with the diabetic group. INPs reduced oxidative toxic stress biomarkers in serum, liver and kidney of the diabetic treated group. Furthermore, a histopathological change was developed in the treated groups. Conclusion: Capsulated INPs can prevent diabetic liver and oxidative kidney damages (similar regular insulin). Therefore oral administration of INPs appears to be safe. Lay Summary: Although oral route is the most preferred route of administration, but oral delivery of peptides and proteins is still a challenging issue. Diabetes Mellitus may lead to severe complications, which most of them are life-threatening. In this study, we are testing the toxicity of oral insulin nanoparticles in kidney and liver of rats. For this investigation, we will prepare insulin nanoparticles composed of a quaternized derivative of chitosan. The nanoparticles will be administered orally to rats and the level of oxidative stress in their liver and kidney will be determined. The data will be compared to the subcutaneous injection of insulin.
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Pincekova, Lucia, and Dusan Berkes. "Synthesis of (2S,3S)-3-Aroyl Pyroglutamic Acid Amides." Cells 3, no. 1 (November 14, 2020): 86. http://dx.doi.org/10.3390/ecsoc-24-08377.
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A new methodology for the asymmetric synthesis of enantiomerically enriched 3-aroyl pyroglutamic acid derivatives has been developed through effective 5-exo-tet cyclization of N-chloroacetyl aroylalanines. The three-step sequence starts with the synthesis of N-substituted (S,S)-2-amino-4-aryl-4-oxobutanoic acids via highly diastereoselective tandem aza-Michael addition and crystallization-induced diastereomer transformation (CIDT). Their N-chloroacetylation followed by base-catalyzed cyclization and ultimate acid-catalyzed removal of chiral auxiliary without loss of stereochemical integrity furnishes the target substituted pyroglutamic acids. Finally, several series of their benzyl amides were prepared as 3-aroyl analogs of known P2X7 antagonists.
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El-Sawy, Eslam, Adel Mandour, Khaled Mahmoud, Inas Islam, and Heba Abo-Salem. "Synthesis, antimicrobial and anti-cancer activities of some new N-ethyl, N-benzyl and N-benzoyl-3-indolyl heterocycles." Acta Pharmaceutica 62, no. 2 (June 1, 2012): 157–79. http://dx.doi.org/10.2478/v10007-012-0020-3.
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Synthesis, antimicrobial and anti-cancer activities of some newN-ethyl,N-benzyl andN-benzoyl-3-indolyl heterocyclesA series of 1-(N-substituted-1H-indol-3-yl)-3-arylprop-2-ene-1-ones (2a, b-4a, b) were prepared and allowed to react with urea, thiourea or guanidine to give pyrimidine derivatives5a, b-13a, b. Reaction of2a, b-4a, bwith ethyl acetoacetate in the presence of a base gave cyclohexanone derivatives14a, b-16a, b. Reaction of the latter compounds with hydrazine hydrate afforded indazole derivatives17a, b-19a, b. On the other hand, reaction of2a, b-4a, bwith some hydrazine derivatives, namely hydrazine hydrate, acetyl hydrazine, phenylhydrazine and benzylhydrazine hydrochloride, led to the formation of pyrazole derivatives20a, b-31a, b. Moreover, reaction of2a, b-4a, bwith hydroxylamine hydrochloride gave isoxazole derivatives32a, b-34a, b. The newly synthesized compounds were tested for their antimicrobial activity and showed that 4-(N-ethyl-1H-indol-3-yl)-6-(p-chlorophenyl)-pyrimidine-2-amine (11b) was the most active of all the test compounds towardsCandida albicanscompared to the reference drug cycloheximide. Eighteen new compounds, namely pyrimidin-2(1H)-ones5a, b-7a, b, pyrimidin-2(1H)-thiones8a, b-10a, band pyrimidin-2-amines11a, b-13a, bderivatives, were tested for theirin vitroantiproliferative activity against HEPG2, MCF7 and HCT-116 cancer cell lines. 4-(N-ethyl-1H-indol-3-yl)-6-(p-methoxyphenyl)-pyrimidin-2-amine (11a)was found to be highly active withIC50of 0.7 μmol L-1.
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Alagarsamy, Veerachamy, Viswas Solomon, G. Krishnamoorthy, M. T. Sulthana, and B. Narendar. "Synthesis and antimicrobial activities of 1-(3-benzyl-4-oxo-3H-quinazolin-2-yl)-4-(substituted)thiosemicarbazide derivatives." Journal of the Serbian Chemical Society 80, no. 12 (2015): 1471–79. http://dx.doi.org/10.2298/jsc150103053a.
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A series of 1-(3-benzyl-4-oxo-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides (AS1-AS10) were obtained by the reaction of 2-hydrazino- 3-benzyl quinazolin-4(3H)-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate 3-benzyl-2-thioxo-2,3-dihydro-1Hquinazolin-4-one (4) was obtained by reacting benzyl amine (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulfate to yield the dithiocarbamic acid methyl ester (2) and condensed with methyl anthranilate (3) in ethanol yielded the desired compound (4) via the thiourea intermediate. The SH group of compound (4) was methylated for the favorable nucleophilic displacement reaction with hydrazine hydrate, which afford 2-hydrazino-3- benzyl-3H-quinazolin-4-one (6). The IR, 1H, and 13C NMR spectrum of these compounds showed the presence of peaks due to thiosemicarbazides, carbonyl (C=O), NH and aryl groups. The quinazolin-4-one moiety molecular ion peaks (m/z 144) were observed all the mass spectrum of compounds (AS1-AS10). Elemental (C, H, N) analysis satisfactorily confirmed purity of the synthesized compounds and elemental composition. All synthesized compounds were also screened for their antimicrobial activity against selective gram positive and gram negative by agar dilution method. In the present study compounds AS8 and AS9 were emerged as the most active compounds of the series.
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Giongo, Viveca, Annarita Falanga, Camilly P. Pires De Melo, Gustavo B. da Silva, Rosa Bellavita, Salvatore G. De-Simone, Izabel C. Paixão, and Stefania Galdiero. "Antiviral Potential of Naphthoquinones Derivatives Encapsulated within Liposomes." Molecules 26, no. 21 (October 25, 2021): 6440. http://dx.doi.org/10.3390/molecules26216440.
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HSV infections, both type 1 and type 2, are among the most widespread viral diseases affecting people of all ages. Their symptoms could be mild, with cold sores up to 10 days of infection, blindness and encephalitis caused by HSV-1 affecting immunocompetent and immunosuppressed individuals. The severe effects derive from co-evolution with the host, resulting in immune evasion mechanisms, including latency and growing resistance to acyclovir and derivatives. An efficient alternative to controlling the spreading of HSV mutations is the exploitation of new drugs, and the possibility of enhancing their delivery through the encapsulation of drugs into nanoparticles, such as liposomes. In this work, liposomes were loaded with a series of 2-aminomethyl- 3-hydroxy-1,4-naphthoquinones derivatives with n-butyl (compound 1), benzyl (compound 2) and nitrobenzene (compound 3) substituents in the primary amine of naphthoquinone. They were previously identified to have significant inhibitory activity against HSV-1. All of the aminomethylnaphthoquinones derivatives encapsulated in the phosphatidylcholine liposomes were able to control the early and late phases of HSV-1 replication, especially those substituted with the benzyl (compound 2) and nitrobenzene (compound 3), which yields selective index values that are almost nine times more efficient than acyclovir. The growing interest of the industry in topical administration against HSV supports our choice of liposome as a drug carrier of aminomethylnaphthoquinones derivatives for formulations of in vivo pre-clinical assays.
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Solomyannyi, Roman, Sergii Slivchuk, Donald Smee, Jung-ae Choi, Eduard Rusanov, Victor Zhirnov, and Volodymyr Brovarets. "In vitro Activity of the Novel Pyrimidines and Their Condensed Derivatives Against Poliovirus." Current Bioactive Compounds 15, no. 5 (January 3, 2019): 582–91. http://dx.doi.org/10.2174/1573407214666180720120509.
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Background: Substituted pyrimidine derivatives (non-nucleoside) are found to be associated with various biological activities. The various substituted pyrimidines are also having significant in vitro activity against different DNA and RNA viruses. The present study focuses on the anti-PV activity of new pyrimidines and their condensed derivatives. Methods: A series of novel pyrimidines and their condensed derivatives were synthesized and their structures were confirmed by spectral data. Their antiviral activities against poliovirus type 3 (PV-3) were evaluated in vitro. In cell culture, morphological changes observed in cells infected with polioviruses, including cell rounding and detachment from the substrate, are generally termed cytopathic effects (CPE). The effects of synthetic pyrimidines on PV amplification in a culture of the heteroploid cell line, Vero 76 (African green monkey kidney cells) were investigated. Results: Bioassays in vitro showed that one of seven synthesized compounds, 7-(Benzenesulfonyl)-5- benzyl-N-(prop-2-en-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine, has potent antiviral activity against PV-3 (EC50 = 0.75 μM). The selectivity index of this compound is similar to that of pirodavir. Conclusion: The need for antiviral agents to treat PV-associated diseases remains great, but few options currently exist. Here we show that substituted pyrimidine derivatives are a promising structure class of chemical compounds for the development of antiviral drugs against PV infections.
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Szakonyi, Zsolt, Reijo Sillanpää, and Ferenc Fülöp. "Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides." Beilstein Journal of Organic Chemistry 10 (November 21, 2014): 2738–42. http://dx.doi.org/10.3762/bjoc.10.289.
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The Michael addition of dibenzylamine to (+)-tert-butyl perillate (3) and to (+)-tert-butyl phellandrate (6), derived from (S)-(−)-perillaldehyde (1), resulted in diastereomeric β-amino esters 7A–D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A–D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied and, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.
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Guillon, Jean, Anita Cohen, Nassima Meriem Gueddouda, Rabindra Nath Das, Stéphane Moreau, Luisa Ronga, Solène Savrimoutou, et al. "Design, synthesis and antimalarial activity of novel bis{N-[(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]-3-aminopropyl}amine derivatives." Journal of Enzyme Inhibition and Medicinal Chemistry 32, no. 1 (January 1, 2017): 547–63. http://dx.doi.org/10.1080/14756366.2016.1268608.
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Olgen, S., A. Kaessler, Z. Kilic Kurt, and J. Jose. "Structure-Activity Evaluation of N-benzyl-5-substituted Indole-3-imine Derivatives and their Amine Congeners as Bovine Testicular Hyaluronidase (BTH) Inhibitor." Letters in Drug Design & Discovery 8, no. 8 (October 1, 2011): 685–90. http://dx.doi.org/10.2174/157018011796576079.
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Murtaza, Shahzad, Ataf Ali Altaf, Muhammad Hamayun, Kiran Iftikhar, Muhammad Nawaz Tahir, Javaria Tariq, and Khadija Faiz. "Synthesis, antibacterial activity and docking studies of chloroacetamide derivatives." European Journal of Chemistry 10, no. 4 (December 31, 2019): 358–66. http://dx.doi.org/10.5155/eurjchem.10.4.358-366.1859.
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Structural modification of lead compounds is a great challenge in organic synthesis. Introduction of different functional groups not only modify the structure of starting material but also improve their biological activeness. Small synthetic molecules are favored in spite of the reality that majority of drug molecules derived from natural sources, are in vogue. In the present work, acetamide derivatives were synthesized using chloroacetyl chloride. After synthesizing targeted series of acetamide derivatives these compounds were further modified using different amines including 2-aminobenzene thiol, benzyl amine, benzene 1,4-diamine, 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, 4-aminophenol, hydrazine and 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide. All of these synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR and X-ray crystallography. The compounds were assessed for their anti-bacterial activity using disc diffusion method against Staphylococcus aureus and Escherichia coli. The compounds were found to exhibit comparable activity to the standard drug used. This was further supported by molecular docking studies using bacterial DNA gyrase and Topoisomerase II targets causing bacterial death as they are major bacterial proteins known to be involved in transcription and replication process. Results proved that the compound 2b was the most efficacious antimicrobial compound among the synthesized set of compounds. To tackle the growing drug resistance acetamide based functionalities can be regarded as the active lead compounds to target different drug resistance microorganism.
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Prasad, Tangella Nagendra, Yeruva Pavankumar Reddy, Poorna Chandrasekhar Settipalli, Vadiga Shanthi Kumar, Eeda Koti Reddy, Shaik Firoj Basha, and Shaik Anwar. "Synthesis of trans N-Substituted Pyrrolidine Derivatives Bearing 1,2,4-triazole Ring." Current Organic Synthesis 19 (December 30, 2021). http://dx.doi.org/10.2174/1570179419666211230094334.
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Background: 1,2,4-triazoles scaffolds display significant biological activities due to hydrogen bonding, solubility, dipole character, and rigidity Objective: The core motif of 1,2,4-triazoles plays a vital role in clinical drugs such as Rizatriptan (anti-migraine), Ribavirin (antiviral), anastrozole (anticancer), etizolam (anxiolytic), estazolam (anticonvulsant), alprazolam (anti-hypnotic), letrozole (aromatase inhibitor), loreclezole (anticonvulsant), trazadone (antidepressant) etc Method: Epoxide ring opening of tert-butyl 6-oxa-3-azabicyclo [3.1.0] hexane-3-carboxylate followed by methylation under basic conditions and de-protection gave the corresponding trans 1-(4-methoxypyrrolidin-3-yl)-1H-1,2,4-triazole hydrochloride salt as the precursor. This precursor on reaction with substituted benzoyl chlorides and benzyl bromides gave the desired amide and amine products Results: A library of 14 N-substituted pyrrolidine derivatives i.e. trans3-methoxy-4-(1H-1,2,4-triazol-1-yl) pyrrolidin-1-yl) (phenyl)methanone and trans 1-benzyl-4-methoxypyrrolidin-3-yl)-1H-1,2,4-triazole were prepared Conclusion: Eight novel amides (6a-h) and six amines (8a-f) derivatives were synthesized using 1-(4-methoxypyrrolidin-3-yl)-1H-1,2,4-triazole 4 salt with substituted benzoyl chlorides and benzyl bromides.
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Nesterova, Olga, Dmitrii Babaskin, Yuliya Tikhonova, Natalia Molodozhnikova, and Sergey Kondrashev. "Effect of N'-Benzyl Substituted Uracil and the Analogues on HIV-1 Inhibition." Research Journal of Pharmacy and Technology, May 26, 2021, 2723–28. http://dx.doi.org/10.52711/0974-360x.2021.00480.
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The aim of the research is to study the effect of the synthesis of uracil derivatives on the HIV-1 activity. To achieve the goal, the following tasks were determined: to study the specificity of possible compounds for HIV-1 treatment; to synthesize uracil derivatives; to study the effect of the compounds on HIV-1 replication in vitro and select the most optimal concentrations, considering the cytotoxic effect; to determine the most effective anti-HIV-1 compounds for further research. Thus, nine new uracil analogues have been synthesized and proved to be inhibitors of HIV-1. Key structural modifications included replacement of the 6-chloro group of 1-benzyl-6-chloro-3-(3,5-dimethylbenzyl) uracil by other functional groups or N (1)-alkylation of 3-(3,5-dimethylbenzyl)-5-fluorouracil. These compounds showed only micromolar potency against HIV-1 in MT-4, though two of them; 6-azido-1-benzyl-3-(3,5-dimethylbenzyl) uracil and 6-amino-1-benzyl-3-(3,5-dimethylbenzyl) uracil were highly potent (half maximal effective concentration =0.081 and 0.069μM) and selective (selectivity index =679 and 658), respectively. Structure-activity relationships among the newly synthesized uracil analogues suggest the importance of the H-bond formed between 6-amino group of 6-amino-1-benzyl-3-(3,5-dimethylbenzyl) uracil and amide group of HIV-1 reverse transcriptase. Two 6-substituted 1-benzyl-3-(3,5-dimethylbenzyl) uracils, (6-azido-1-benzyl-3-(3,5-dimethylbenzyl) uracil and 6-amino-1-benzyl-3-(3,5-dimethylbenzyl) uracil) were discovered as novel anti-HIV agents. Compound’s activity against HIV-1 was determined based on inhibition of virus-induced cytopathogenicity in MT-4 cells. The compounds were tested for efficacy in infected cells and cytotoxicity. These compounds should be further pursued for their toxicity and pharmacokinetics in vivo as well as antiviral activity against non-nucleoside reverse transcriptase inhibitor-resistant strains. Thus, it will contribute to the development of a new generation of compounds effective against different viruses, considering their quickly mutation and increased resistance.