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Academic literature on the topic 'Trifluoromethyl compounds'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Trifluoromethyl compounds"

1

Lahsasni, Siham, Dunya A. M. Al-Hemyari, Hazem A. Ghabbour, et al. "Synthesis, Characterization, and Antibacterial and Anti-Inflammatory Activities of New Pyrimidine and Thiophene Derivatives." Journal of Chemistry 2018 (August 1, 2018): 1–11. http://dx.doi.org/10.1155/2018/8536063.

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Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-one (3a–b) and pyrimidin-5(6H)-imine (3c–e) were synthesized via reaction of the starting compounds, ethyl 2-amino-substituted[b]thiophene-3-carboxylate (2a–c) and 2-amino-substituted [b]thiophene-3-carbonitrile (2d–f), respectively, with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl)alkanamide derivatives (4a–e) and thieno[2,3-d][1,3]oxazin-4-imine derivative (5) was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of compound 5, nucleophilic substitution was followed by nucleophilic addition to a nitrile group to form the oxazinimine ring. 1-(3-cyano-substituted[b]thiophen-2-yl)-3-(4-(trifluoromethyl)phenyl)thiourea derivatives (6a–c) were obtained via reaction of the starting compounds (2d–f) and 4-(trifluoromethyl phenyl)isothiocyanate. The lead compounds (2d–f) rapidly reacted with 4-(trifluoromethyl)benzaldehyde or 4-(2-pyridyl)benzaldehyde in acidic medium to yield compounds (7a–f) in large quantities. X-ray crystallography of compounds 4c and 7e confirmed their structures. Antimicrobial studies revealed that compound 6a was equally potent to ampicillin against Bacillus strains. Moreover, compounds 3e, 4d, and 6a possessed greater anti-inflammatory potency than that of the standard drug.
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2

Zouaoui, Emna, and Mohamed Moncef El Gaïed. "Synthesis of Trifluoromethyl Heterocyclic Compounds." Journal of Chemical Research 2003, no. 4 (2003): 242–46. http://dx.doi.org/10.1177/1747519803200300404.

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3

Hafez, Hend N., and Abdel-Rahman B. A. El-Gazzar. "Synthesis of Novel Pyridine Bearing Biologically Active Imidiazolyl, Pyrazolyl, Oxa/thiadiazolyl and Urea Derivatives as Promising Anticancer Agents." Current Organic Synthesis 17, no. 1 (2020): 55–64. http://dx.doi.org/10.2174/1570179417666191223163225.

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Background: A novel series of pyridine containing 1,3,4-oxa/thiadiazol derivatives 4a,b, pyrazole derivatives 5-7, thiazole derivatives 9a,b and 17a-c, urea derivatives 12a-c, imidiazole derivative 16, imidazo[1,2-a]pyridine derivatives 18a, b, tetrazole 19, pyrane 20 and pyridine derivatives 21 has been synthesized. Objective: This research aims to synthesize 6-(Trifluoromethyl)-2-[3-(trifluoromethyl)phenyl] amino nicotinohydrazide 2 and 6-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino pyridin-3-carboaldhyde 15 as key intermediate for the synthesis of novel pyridine derivatives bearing different heterocyclic rings in order to study the additive effect of this ring toward tumor cell lines. Methods: 6-(Trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino nicotinohydrazide 2 was synthesized in a series of synthetic steps and was used as key intermediate for the synthesis of compounds 3-(1,3,4- oxa/thiadiazol-2-yl)-6-(trifluoromethyl)-N-(3- trifluoromethyl) phenyl) pyridin-2-amine 4a,b, (3,5-dimethyl- 1H-pyrazol-1-yl derivatives) [6-(trifluoromethyl)-2-[3- trifluoromethyl) phenyl] amino pyridin-3- yl]methanone 5a,b, 6-8, 9a,b and 12a-c. Also, 6-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino pyridin-3-carboaldhyde (15) was used as a key intermediate for the synthesis of novel series of pyridine derivatives with different heterocyclic ring (16-21). Results: Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All the synthesized compounds were screened for their in vitro anticancer activity against liver cancer (HepG2), human colon cancer (HT-29) and human breast adenocarcinoma cell lines (MCF-7). Conclusion: All the synthesized compounds were investigated for their in vitro antitumor activity. Compounds 4b, 9a,b and 19 showed higher antitumor activity than the doxorubicin. Interestingly, pyridine with pfluorophenyl urea 12a demonstrated the most potent antitumor activity. The activity of these compounds is strongly dependent on the basic skeleton of the molecules and the nature of the heterocyclic ring attached to the pyridine moiety.
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4

Zouaoui, Emna, and Mohamed Moncef El Gaïed. "Synthesis of trifluoromethyl heterocyclic compounds." Journal of Chemical Research 2003, no. 4 (2003): 242–46. http://dx.doi.org/10.3184/030823403103173651.

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5

Mandadi, Manoj Kumar, Ramana Reddy Bobbala, Balakrishna Kolli, and Rambabu Gundla. "Synthesis and Anticancer Activity of Novel Amide Tagged Trifluoromethyl Indole and Pyrimido Indole Derivatives." Asian Journal of Chemistry 33, no. 10 (2021): 2327–32. http://dx.doi.org/10.14233/ajchem.2021.23313.

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A series of novel amide tagged trifluoromethyl indole and pyrimido indole derivatives 4a-e & 5a-e and 6a-d & 7a-d were synthesized from 4-methyl-2-(methylamino)-6-(trifluoromethyl)isophthalonitrile (1) on reaction with bromoethyl acetate to obtain 2a and 2b isomers. Compound 2a treated with hydrazine hydrate followed by Schiff base reaction to get compounds 4a-e. In another way, compound 2a on reaction with aliphatic primary amine to get compounds 6a-d. For cyclization, compounds 4a-e & 6a-d treated with trifluoroacetic acid to obtain compounds 5a-e and 7a-d, respectively. All the synthesized compounds 4a-e & 5a-e and 6a-d & 7a-d were tested for anticancer activity against four human cancer cell lines such as A549-lung cancer (CCL-185), MCF7-breast cancer (HTB-22), DU145-prostate cancer (HTB-81) and HeLa-cervical cancer (CCL-2). Compounds 9e and 9f were found to have promising anticancer activity at micromolar concentration.
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6

Suchetan, P. A., E. Suresha, S. Naveen, and N. K. Lokanath. "Crystal structures of 3-fluoro-N-[2-(trifluoromethyl)phenyl]benzamide, 3-bromo-N-[2-(trifluoromethyl)phenyl]benzamide and 3-iodo-N-[2-(trifluoromethyl)phenyl]benzamide." Acta Crystallographica Section E Crystallographic Communications 72, no. 6 (2016): 819–23. http://dx.doi.org/10.1107/s2056989016007866.

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In the title compounds, C14H9F4NO, (I), C14H9BrF3NO, (II), and C14H9F3INO, (III), the two benzene rings are inclined to one another by 43.94 (8)° in moleculeAand 55.66 (7)° in moleculeBof compound (I), which crystallizes with two independent molecules in the asymmetric unit, but by only 10.40 (12)° in compound (II) and 12.5 (2)° in compound (III). In the crystals of all three compounds, N—H...O hydrogen bonds link the molecules to form chains propagating along thea-axis direction for (I), and along theb-axis direction for (II) and (III). In the crystal of (I), –A–B–A–B– chains are linked by C—H...O hydrogen bonds, forming layers parallel to (010). Within the layers there are weak offset π–π interactions present [intercentroid distances = 3.868 (1) and 3.855 (1) Å]. In the crystals of (II) and (III), the chains are linkedviashort halogen–halogen contacts [Br...Br = 3.6141 (4) Å in (II) and I...I = 3.7797 (5) Å in (III)], resulting in the formation of ribbons propagating along theb-axis direction.
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7

Gajdoš, Peter, Soňa Pavlíková, Filip Bureš, and Alžbeta Krutošíková. "2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions." Open Chemistry 3, no. 2 (2005): 311–25. http://dx.doi.org/10.2478/bf02475999.

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AbstractThe synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.
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8

Liang, Yumeng, Akihito Taya, Zhengyu Zhao, Norimichi Saito, and Norio Shibata. "Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions." Beilstein Journal of Organic Chemistry 16 (December 14, 2020): 3052–58. http://dx.doi.org/10.3762/bjoc.16.254.

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A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD® and Olah’s reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.
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9

Betala, Sailu, Hanumandlu Racha, and Chiranjeevi Abba. "Synthesis of Novel Triazolothione, Thiadiazole, Triazole and Oxadiazole Functionalized Tri-fluoromethylnaphthyridine Derivatives and their Anticancer Activity & Antimicrobial Activity." Asian Journal of Chemistry 32, no. 8 (2020): 1931–40. http://dx.doi.org/10.14233/ajchem.2020.22688.

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Novel triazolothione, thiadiazole, triazole and oxadiazole-tagged trifluoromethyl group containing naphthyridine derivatives (6a-l and 7a-d) were synthesized from 2-amino-6-(thiophen-2-yl)-4- (trifluoromethyl)nicotinonitrile (1) on treatment with acetophenone and obtained 2-phenyl-7-(thiophen- 2-yl)-5-(trifluoromethyl)-1,8-naphthyridin-4-amine (2), compound 2 on reaction with bromoethylacetate and after that reaction with hydrazine hydrate and obtained carbohydrazide derivatives (4), compound 4 on reaction with different substituted phenyl isothiocyanates to obtain phenyl hydrazine carbothiamide derivatives (5). Compound 5 is independently reaction with NaOH, H2SO4 and N2H4·H2O to obtain triazolothione, thiadiazole, triazole-substituted naphthyridine derivatives (6a-l), respectively. The carbohydrazide compounds 4 on reaction with diverse substituted aromatic acids and obtained oxadiazole derivatives (7a-d). All the synthesized compounds (6a-l and 7a-d) were tested for anticancer activity against four cancer cell lines such as “HeLa-cervical cancer (CCL-2) COLO 205-colon cancer (CCL-222) HepG2-liver cancer (HB-8065) MCF7-breast cancer (HTB-22) and one normal cell line (HEK 293)”. Compounds 6b, 6d and 6l are known to have good anticancer activity at micro molar concentration and found to be non-toxic on normal cell line. And all the products 6a-o and 7a-d were tested against Gram-positive, Gram-negative bacteria and fungal strains. All the compounds, compounds 6e-h showed more activity against Bacillus subtilis (MTCC-121) at < 6.8 micromolar concentration. Compounds (which showed more activity) further screened for minimum bactericidal concentration against B. subtilis MTCC 121 using ciprofloxacin as standard and known to show optimistic activity. These compounds further tested for biofilm inhibition activity against B. subtilis MTCC 121 using erythromycin as standard which confirmed the high activity.
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10

Beara, Ivana, Tatjana Majkić, Stefania Fioravanti, et al. "The Effects of Trifluoromethylated Derivatives on Prostaglandin E2 and Thromboxane A2 Production in Human Leukemic U937 Macrophages." Medicinal Chemistry 16, no. 1 (2020): 63–68. http://dx.doi.org/10.2174/1573406415666190208150253.

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Background: A convenient approach to modulation of the inflammation has an influence on the production of inflammatory mediators – icosanoids, generated in arachidonic acid (AA) metabolism. The common therapeutic activity of non-steroidal anti-inflammatory drugs (NSAID), such as aspirin, includes inhibition of two crucial enzymes of AA metabolism - cyclooxygenase- 1 and -2 (COX-1/2), with certain risk for gastrointestinal and renal intolerance. Ever since the enrolment of COX-2, particularly overabundance of its main products prostaglandin E2 (PGE2) and thromboxane A2 (TXA2) in numerous pathological processes was recognized, it became a significant therapeutic target. Objective: The aim of this study was to examine the effects of synthesized organo-fluorine compounds on PGE2 and TXA2 production in the inflammation process. Methods: Trifluoromethyl compounds were synthesized from N-benzyl trifluoromethyl aldimine, commercially available 2-methyl or 2-phenyl α-bromo esters (β-lactams trans-1 and trans-2 and trifluoromethyl β-amino ester, respectively) and methyl 2-isocyanoacetate (2-imidazoline trans-4). The reactions proceeded with high geometric selectivity, furnishing the desired products in good yields. The influence of newly synthesized compounds on PGE2 and TXA2 production in human leukemic U937 macrophages on both enzyme activity and gene expression levels was observed. Results: Among the tested trifluoromethyl compounds, methyl trans-1-benzyl-5-(trifluoromethyl)- 4,5-dihydro-1H-imidazole-4-carboxylate (trans-4) can be distinguished as the most powerful antiinflammatory agent, probably due to its trifluoromethyl-imidazoline moiety. Conclusion: Some further structural modifications in tested compounds and particularly in the synthesis of different trifluoromethyl imidazolines could contribute to the development of new COX-2 inhibitors and potent anti-inflammatory agents.
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