Journal articles: 'Trifluoromethyl compounds'

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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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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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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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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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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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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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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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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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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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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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NAGAI, Takabumi, and Itsumaro KUMADAKI. "Ene Reaction of Trifluoromethyl Carbonyl Compounds." Journal of Synthetic Organic Chemistry, Japan 49, no. 7 (1991): 624–35. http://dx.doi.org/10.5059/yukigoseikyokaishi.49.624.

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12

Wakselman, C. "Synthesis of trifluoromethyl-substituted cyclic compounds." Journal of Fluorine Chemistry 58, no. 2-3 (1992): 157. http://dx.doi.org/10.1016/s0022-1139(00)80604-1.

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Jiang, Yuanye, Haizhu Yu, Yao Fu, and Lei Liu. "Redox potentials of trifluoromethyl-containing compounds." Science China Chemistry 58, no. 4 (2014): 673–83. http://dx.doi.org/10.1007/s11426-014-5178-8.

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Sagar, Belakavadi K., Kachigere B. Harsha, Hemmige S. Yathirajan, Kanchugarakoppal S. Rangappa, Ravindranath S. Rathore, and Christopher Glidewell. "Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions." Acta Crystallographica Section C Structural Chemistry 73, no. 3 (2017): 298–304. http://dx.doi.org/10.1107/s205322961700273x.

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In each of 1-(4-fluorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C21H19F4N3O2S, (I), 1-(4-chlorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C21H19ClF3N3O2S, (II), and 1-(3-methylphenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C22H22F3N3O2S, (III), the reduced pyridine ring adopts a half-chair conformation with the methylsulfonyl substituent occupying an equatorial site. Although compounds (I) and (II) are not isostructural, having the space groups Pbca and P212121, respectively, their molecular conformations are very similar, but the conformation of compound (III) differs from those of (I) and (II) in the relative orientation of the N-benzyl and methylsulfonyl substituents. In compounds (II) and (III), but not in (I), the trifluoromethyl groups are disordered over two sets of atomic sites. Molecules of (I) are linked into centrosymmetric dimers by C—H...π(arene) hydrogen bonds, molecules of (II) are linked by two C—H...O hydrogen bonds to form ribbons of R 3 3(18) rings, which are themselves further linked by a C—Cl...π(arene) interaction, and a combination of C—H...O and C—H...π(arene) hydrogen bonds links the molecules of (III) into sheets. Comparisons are made with the structures of some related compounds.

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Krátký, Martin, Katarína Svrčková, Quynh Anh Vu, Šárka Štěpánková, and Jarmila Vinšová. "Hydrazones of 4-(Trifluoromethyl)benzohydrazide as New Inhibitors of Acetyl- and Butyrylcholinesterase." Molecules 26, no. 4 (2021): 989. http://dx.doi.org/10.3390/molecules26040989.

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Based on the broad spectrum of biological activity of hydrazide–hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated hydrazones obtained from 4-(trifluoromethyl)benzohydrazide and various benzaldehydes or aliphatic ketones as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). They were evaluated using Ellman’s spectrophotometric method. The hydrazide–hydrazones produced a dual inhibition of both cholinesterase enzymes with IC50 values of 46.8–137.7 µM and 19.1–881.1 µM for AChE and BuChE, respectively. The majority of the compounds were stronger inhibitors of AChE; four of them (2-bromobenzaldehyde, 3-(trifluoromethyl)benzaldehyde, cyclohexanone, and camphor-based 2o, 2p, 3c, and 3d, respectively) produced a balanced inhibition of the enzymes and only 2-chloro/trifluoromethyl benzylidene derivatives 2d and 2q were found to be more potent inhibitors of BuChE. 4-(Trifluoromethyl)-N’-[4-(trifluoromethyl)benzylidene]benzohydrazide 2l produced the strongest inhibition of AChE via mixed-type inhibition determined experimentally. Structure–activity relationships were identified. The compounds fit physicochemical space for targeting central nervous systems with no apparent cytotoxicity for eukaryotic cell line together. The study provides new insights into this CF3-hydrazide–hydrazone scaffold.

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Gomes, Lígia R., Emerson T. da Silva, Marcus V. N. de Souza, James L. Wardell, and John N. Low. "Crystal structures, Hirshfeld surface analysis and Pixel energy calculations of three trifluoromethylquinoline derivatives: further analyses of fluorine close contacts in trifluoromethylated derivatives." Zeitschrift für Naturforschung B 74, no. 11-12 (2019): 791–810. http://dx.doi.org/10.1515/znb-2019-0109.

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AbstractAs many studies have revealed, the introduction of a CF3 group into an organic compound can result in significant enhancement of biological activity. Factors which lead to this enhancement are thus of great interest. To investigate further this area, we have looked at the ability of fluorine to form close contacts with various atoms in organic compounds, e.g. F⋯F, F⋯O/O⋯F, F⋯C/C⋯F, H⋯F/F⋯H, and F⋯N/N⋯F, as indicated from crystal structure determinations and Hirshfeld analysis studies on trifluoromethylated compounds. Herein we first report the crystal structures, Hirshfeld surface analyses (HSA), and Pixel energy calculations of three trifluoromethylated quinoline derivatives, namely 2-(trifluoromethyl)quinolin-4-ol, 1, 4-ethoxy-2-(trifluoromethyl)quinoline, 2, and N1-(2,8-bis(trifluoromethyl)quinolin-4-yl)ethane-1,2-diamine, 3. Of particular interest is the determination of the various fluorine⋯atom close contacts. The total percentages of fluorine⋯atom close contacts in compounds 1–3 were determined to be high at 47, 41.2 and 60.7%, respectively. As relatively few HSA studies on trifluoromethylated compounds have reported the percentages of individual atom⋯atom close contacts, we have also determined the percentages of atom⋯atom close contacts for 20 more trifluoromethylated compounds: the range of total fluorine⋯atom close contacts for these compounds was 20–60%. While these data are based on connections between similar molecules in a crystalline state, they also clearly suggest that a compound containing CF3 group(s) has the potential to make extensive intermolecular connections/close contacts with organic material. Thus a possible factor for the enhanced biological activity of a compound bearing CF3 group(s) could be the propensity of the CF3 group to form many close contacts, thereby aiding binding or interaction with a biological target.

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Break, Laila Mohammed, та Wafa Saad Al-harthi. "Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone". Proceedings 9, № 1 (2018): 57. http://dx.doi.org/10.3390/ecsoc-22-05694.

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Fluorinated nucleosides are very important for increased biological and chemical stability of organ fluorine compounds. Synthesis of (1H)-8-trifluloromethyl-2-methyl-4-quinazolinone 3 from 2-amino-3-(trifluoromethyl) benzoic acid 1 was performed. Ribosylation of compound 4 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose 5 using the silylation method created the benzoylated nucleoside derivative 6. Debenzoylation of the protected nucleoside 6 via reaction with sodium metal in dry methanol to create the corresponding free nucleoside 1,3-bis-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)-8-(trifluoromethyl)-2-methyl-4-quinazolinone 7. The structures of the newly synthesis compounds have been confirmed on the basis of IR, 1HNMR, 13CNMR, and mass spectral data.

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Ienascu, Ioana M. c., Alfa X. Lupea, Iuliana M. Popescu, Stefan Th Tomas, and Alina D. Zamfir. "Synthesis and Characterization of Some New 2-Hydroxy-N-(3-Trifluoromethyl-Phenyl)-Benzamide Derivatives." Revista de Chimie 59, no. 1 (2008): 56–60. http://dx.doi.org/10.37358/rc.08.1.1707.

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In the reaction between 2-hydroxy-N-(3-trifluoromethyl-phenyl)-benzamide and chloro-acetic acid ethyl ester, [2-(3-trifluoromethyl-phenylcarbamoyl)-phenoxy]-acetic acid ethyl ester was obtained. The ethyl ester was condensed with hydrazine giving 2-hydrazinocarbonylmethoxy-N-(3-trifluoromethyl-phenyl)-benzamide. This hydrazide is considered the key intermediate for the synthesis of new compounds. So, in the reaction between hydrazide and chloro-substituted benzaldehydes hydrazones were obtained. In order to establish their structures, all new synthesized compounds were analyzed by modern physico-chemical methods (FTIR, 1H-NMR, 13C-NMR, MS).

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Chavchich, Marina, Geoffrey W. Birrell, Arba L. Ager, et al. "Lead Selection of a New Aminomethylphenol, JPC-3210, for Malaria Treatment and Prevention." Antimicrobial Agents and Chemotherapy 60, no. 5 (2016): 3115–18. http://dx.doi.org/10.1128/aac.03066-15.

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ABSTRACTStructure-activity relationship studies of trifluoromethyl-substituted pyridine and pyrimidine analogues of 2-aminomethylphenols (JPC-2997, JPC-3186, and JPC-3210) were conducted for preclinical development for malaria treatment and/or prevention. Of these compounds, JPC-3210 [4-(tert-butyl)-2-((tert-butylamino)methyl)-6-(5-fluoro-6-(trifluoromethyl)pyridin-3-yl)phenol] was selected as the lead compound due to superiorin vitroantimalarial activity against multidrug-resistantPlasmodium falciparumlines, lowerin vitrocytotoxicity in mammalian cell lines, longer plasma elimination half-life, and greaterin vivoefficacy against murine malaria.

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Barlin, GB, C. Jiravinyu, and JH Yan. "Potential Antimalarials. XIV. Mono-Mannich Bases of 4-[7'-Bromo (and trifluoromethyl)-1',5'-naphthyridin-4'-yl-amino]-5,6,7,8-tetrahydronaphthalen-1-ols." Australian Journal of Chemistry 44, no. 5 (1991): 677. http://dx.doi.org/10.1071/ch9910677.

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The mono- Mannich bases 2-diethylaminomethyl-, 2-t-butylaminomethyl-, 2-(pyrrolidin-1-ylmethyl)-, 2-(piperidin-1-ylmethyl)-, 2-(3-and 4-methylpiperidin-1-ylmethyl)-, 2-(4-benzylpip- eridin-1-ylmethyl)- and 2-(4-benzylpiperazin-1-ylmethyl)-4-[7-bromo (and 7-trifluoromethyl)- 1,5-naphthyridin-4-ylamino]-5,6,7,8-tetrahydronaphthalen-1-ols have been prepared from 4- acetamido-5,6,7,8-tetrahydronaphthalen-1-ols by Mannich reactions followed by hydrolysis to the 4-amino compounds and condensation with the relevant 4-chloro heterocycle. The antimalarial activities of these compounds against the chloroquine -sensitive isolate (FCQ-27) of Plasmodium falciparum in vitro are reported; 4-(7-bromo-1,5-naphthyridin-4-yl)amino-2-(t- butylaminomethyl )-5,6,7,8-tetrahydronaphthalen-1-ol was about twice as active as chloroquine . In in vivo tests against Plasmodium vinckei vinckei in mice this compound exhibited significant activity. The 7-bromo compounds were more active than their 7-trifluoromethyl analogues.

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West, Sheldon D., and Edgar W. Day. "Liquid Chromatographic Determination of Fluridone Aquatic Herbicide and Its Metabolite in Fish and Crayfish." Journal of AOAC INTERNATIONAL 69, no. 5 (1986): 856–59. http://dx.doi.org/10.1093/jaoac/69.5.856.

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Abstract A residue method is described for determination of the aquatic herbicide fluridone (1-methy1-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)- pyridinone) and its metabolite (1-methy1-3-(4-hydroxyphenyl)-5-[3- (trifluoromethyl)phenyl]-4(1H)-pyridinone) in fish and crayfish tissues. Both compounds are extracted from tissues with methanol, and the extracts are subjected to acidic hydrolysis to release conjugated forms of fluridone and the metabolite. Sample extracts are purified by liquidliquid partitioning and Florisil Sep-Pak® column chromatography. Both compounds are separated and measured by reverse phase liquid chromatography with UV detection at 313 nm. In the absence of interfering peaks, the method has a detection limit of approximately 0.04 ppm of either compound. Overall, recoveries averaged 96% for fluridone and 78% for the metabolite for all tissue types combined.

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Kudalkar, Gaurav P., Virendra K. Tiwari, Joshua D. Lee, and David B. Berkowitz. "A Hammett Study of Clostridium acetobutylicum Alcohol Dehydrogenase (CaADH): An Enzyme with Remarkable Substrate Promiscuity and Utility for Organic Synthesis." Synlett 31, no. 03 (2020): 237–47. http://dx.doi.org/10.1055/s-0039-1691576.

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Described is a physical organic study of the reduction of three sets of carbonyl compounds by the NADPH-dependent enzyme Clostridium acetobutylicum alcohol dehydrogenase (CaADH). Previous studies in our group have shown this enzyme to display broad substrate promiscuity, yet remarkable stereochemical fidelity, in the reduction of carbonyl compounds, including α-, β- and γ-keto esters (d-stereochemistry), as well as α,α-difluorinated-β-keto phosphonate esters (l-stereochemistry). To better mechanistically characterize this promising dehydrogenase enzyme, we report here the results of a Hammett linear free-energy relationship (LFER) study across three distinct classes of carbonyl substrates; namely aryl aldehydes, aryl β-keto esters and aryl trifluoromethyl ketones. Rates are measured by monitoring the decrease in NADPH fluorescence at 460 nm with time across a range of substrate concentrations for each member of each carbonyl compound class. The resulting v 0 versus [S] data are subjected to least-squares hyperbolic fitting to the Michaelis–Menton equation. Hammett plots of log(V max) versus σX yield the following Hammett parameters: (i) for p-substituted aldehydes, ρ = 0.99 ± 0.10, ρ = 0.40 ± 0.09; two domains observed, (ii) for p-substituted β-keto esters ρ = 1.02 ± 0.31, and (iii) for p-substituted aryl trifluoromethyl ketones ρ = –0.97 ± 0.12. The positive sign of ρ indicated for the first two compound classes suggests that the hydride transfer from the nicotinamide cofactor is at least partially rate-limiting, whereas the negative sign of ρ for the aryl trifluoromethyl ketone class suggests that dehydration of the ketone hydrate may be rate-limiting for this compound class. Consistent with this notion, examination of the 13C NMR spectra for the set of p-substituted aryl trifluoromethyl ketones in 2% aqueous DMSO reveals significant formation of the hydrate (gem-diol) for this compound family, with compounds bearing the more electron-withdrawing groups showing greater degrees of hydration. This work also presents the first examples of the CaADH-mediated reduction of aryl trifluoromethyl ketones, and chiral HPLC analysis indicates that the parent compound α,α,α-trifluoroacetophenone is enzymatically reduced in 99% ee and 95% yield, providing the (S)-stereoisomer, suggesting yet another compound class for which this enzyme displays high enantioselectivity.

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23

Samigullin, Kamil, Yashar Soltani, Hans-Wolfram Lerner, Matthias Wagner, and Michael Bolte. "Conformational studies on heteroleptic trifluoromethyl-substituted phenylboranes." Acta Crystallographica Section C Structural Chemistry 72, no. 3 (2016): 189–97. http://dx.doi.org/10.1107/s2053229616002242.

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Organoboranes carrying electron-withdrawing substituents are commonly used as Lewis acidic catalysts or cocatalysts in a variety of organic processes. These Lewis acids also became popular through their application in `frustrated Lewis pairs',i.e.combinations of Lewis acids and bases that are unable to fully neutralize each other due to steric or electronic effects. We have determined the crystal and molecular structures of four heteroleptic arylboranes carrying 2-(trifluoromethyl)phenyl, 2,6-bis(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl or mesityl substituents. [3,5-Bis(trifluoromethyl)phenyl]bis[2-(trifluoromethyl)phenyl]borane, C22H11BF12, (I), crystallizes with two molecules in the asymmetric unit which show very similar geometric parameters. In one of the two molecules, both trifluoromethyl groups of the 3,5-bis(trifluoromethyl)phenyl substituent are disordered over two positions. In [3,5-bis(trifluoromethyl)phenyl]bis[2,6-bis(trifluoromethyl)phenyl]borane, C24H9BF18, (II), only one of the twometa-trifluoromethyl groups is disordered. In [2,6-bis(trifluoromethyl)phenyl]bis[3,5-bis(trifluoromethyl)phenyl]borane, C24H9BF18, (III), bothmeta-trifluoromethyl groups of only one 3,5-bis(trifluoromethyl)phenyl ring are disordered. [3,5-Bis(trifluoromethyl)phenyl]dimesitylborane, C26H25BF6, (IV), carries only onemeta-trifluoromethyl-substituted phenyl ring, with one of the two trifluoromethyl groups disordered over two positions. In addition to compounds (I)–(IV), the structure of bis[2,6-bis(trifluoromethyl)phenyl]fluoroborane, C16H6BF13, (V), is presented. None of theortho-trifluoromethyl groups is disordered in any of the five compounds. In all the structures, the boron centre is in a trigonal planar coordination. Nevertheless, the bond angles around this atom vary according to the bulkiness and mutual repulsion of the substituents of the phenyl rings. Also, theortho-trifluoromethyl-substituted phenyl rings usually show longer B—C bonds and tend to be tilted out of the BC3plane by a higher degree than the phenyl rings carryingorthoH atoms. A comparison with related structures corroborates the conclusions regarding the geometric parameters of the boron centre drawn from the five structures in this paper. On the other hand, CF3groups inmetapositions do not seem to have a marked effect on the geometry involving the boron centre. Furthermore, it has been observed for the structures reported here and those reported previously that for CF3groups inorthopositions of the aromatic ring, disorder of the F atoms is less probable than for CF3groups inmetaorparapositions of the ring.

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24

Ahsan, Mohamed Jawed, Mohd Zaheen Hassan, Surender Singh Jadav, et al. "Synthesis and Biological Potentials of 5-aryl-N-[4-(trifluoromethyl) phenyl]-1,3,4-oxadiazol-2-amines." Letters in Organic Chemistry 17, no. 2 (2020): 133–40. http://dx.doi.org/10.2174/1570178616666190401193928.

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Oxadiazoles are an important class of heterocyclic compounds, having broad-spectrum activity. They were also reported as anticancer, and antioxidant agents, hence it is of significant importance to explore new oxadiazoles. A series of eleven (5-aryl-N-[4-(trifluoromethyl)phenyl]-1,3,4- oxadiazol-2-amines (6a-k) was synthesized based on the structures of reported compounds, SU-101, IMC38525, and FTAB. All these oxadiazoles were synthesized, characterized by spectral data, and further tested against melanoma, leukemia, colon, lung, CNS, ovarian, renal, breast and prostate cancer cell lines’ panels at a single dose of 10 μM drug concentrations. N-(4-(Trifluoromethyl)phenyl)-5-(3,4- dimethoxyphenyl)-1,3,4-oxadiazol-2-amine (6h) showed significant anticancer activity, and the most sensitive five cell lines were NCI-H522 (% GI = 53.24), K-562 (% GI = 47.22), MOLT-4 (% GI = 43.87), LOX-IMVI (% GI = 43.62), and HL-60(TB) (% GI = 40.30). The compound, 6h revealed better %GIs than imatinib, against 36 cell lines, taking 54 cell lines in common. The maximum sensitivity was recorded against cancer cell line CCRF-CEM (% GI = 68.89) by 2-(5-(4-(trifluoromethyl) phenylamino)-1,3,4-oxadiazol-2-yl)phenol (6f). The antioxidant activity of 4-(5-(4-(trifluoromethyl) phenylamino)-1,3,4-oxadiazol-2-yl)-2-methoxyphenol (6i) was promising with an IC50 of 15.14 μM. It was observed that the oxadiazoles reported herein showed significant anticancer and antioxidant activities.

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25

Burger, Klaus, Dieter Hübl, and Ralph Ottlinger. "Introduction of trifluoromethyl groups into heterocyclic compounds." Journal of Fluorine Chemistry 29, no. 1-2 (1985): 130. http://dx.doi.org/10.1016/s0022-1139(00)83366-7.

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26

Martínez-Salvador, Sonia, Juan Forniés, Antonio Martín, Babil Menjón, and Isabel Usón. "Stepwise Degradation of Trifluoromethyl Platinum(II) Compounds." Chemistry - A European Journal 19, no. 1 (2012): 324–37. http://dx.doi.org/10.1002/chem.201202648.

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27

Fanqi, Qu, Jiang Hong, Xiao Xuhui, and Huang Xiaoling. "Some new antiphytoviral compounds containing trifluoromethyl group." Wuhan University Journal of Natural Sciences 1, no. 2 (1996): 283–84. http://dx.doi.org/10.1007/bf02901244.

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28

Beus, Maja, Diana Fontinha, Jana Held, Zrinka Rajić, Miguel Prudêncio, and Branka Zorc. "Synthesis and antiplasmodial evaluation of novel mefloquine-based fumardiamides." Acta Pharmaceutica 69, no. 2 (2019): 233–48. http://dx.doi.org/10.2478/acph-2019-0019.

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Abstract The paper is focused on the synthesis and screening of the antiplasmodial activity of novel fumardiamides 5–10 with the mefloquine pharmacophore and a Michael acceptor motif. Multi-step reactions leading to the title compounds included two amide bond formations. The first amide bond was achieved by the reaction of (E)-ethyl 4-chloro-4-oxobut-2-enoate (1) and N1-(2,8-bis(trifluoromethyl)quinolin-4-yl) butane-1,4-diamine (2). The obtained ester 3 was hydrolyzed and gave acid 4, which then reacted with the selected halogenanilines in the presence of HATU/DIEA and formed products 5–10. Title compounds showed marked, dose dependent activity in vitro against hepatic stages of Plasmodium berghei. IC50 values of the most active compounds 5, 7 and 9 bearing 3-fluoro, 3-chloro and 3-trifluoromethyl substituents were 3.04–4.16 µmol L−1, respectively. On the other hand, the compounds exerted only weak activity against the erythrocytic stages of two P. falciparum strains (Pf3D7 and PfDd2) in vitro, with the exception of compound 5 (IC50 = 2.9 µmol L−1).

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29

Barlin, GB, and C. Jiravinyu. "Potential Antimalarials. X. Di-Mannich Bases of 4-(7'-Trifluoromethyl-1',5'-naphthyridin-4'-ylamino)phenol and N-(4'-Diethylamino-1'-methylbutyl)-7-trifluoromethyl-1,5-naphthyridin-4- amine." Australian Journal of Chemistry 43, no. 7 (1990): 1175. http://dx.doi.org/10.1071/ch9901175.

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The syntheses of some di-Mannich bases derived from 4-(7′-trifluoromethyl-1′,5′-naphthyridin-4′-ylamino) phenol and of N-(4′-diethylamino-11′-methylbutyl)-7-trifluoromethyl-1,5-naphthyridin-4- amine from 3-chloro-5-trifluoromethylpyridine via4-chloro-7- trifluoromethyl-1,5-naphthyridine are described. In tests in vitro against the FCQ-27 strain of Plasmodium falciparum these compounds were slightly less active than their 7-bromo analogues.

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30

Nair, H. K., and J. A. Morrison. "Synthesis of bis(trifluoromethyl)phenylthallium and bis(trifluoromethyl)thallium acetate. Oxidative trifluoromethylation with bis(trifluoromethyl)thallium(III) compounds." Inorganic Chemistry 28, no. 14 (1989): 2816–20. http://dx.doi.org/10.1021/ic00313a026.

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31

Diehl III, George L., Lisa Je, and Joseph M. Tanski. "Crystallographic and spectroscopic characterization of 4-nitro-2-(trifluoromethyl)benzoic acid and 4-nitro-3-(trifluoromethyl)benzoic acid." Acta Crystallographica Section E Crystallographic Communications 75, no. 4 (2019): 524–28. http://dx.doi.org/10.1107/s2056989019003979.

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The title compounds, both C8H4F3NO4, represent two isomers of nitro trifluoromethyl benzoic acid. The compounds each contain a nitro functionality para to the carboxylic acid group, with the trifluoromethyl substituent ortho to the acid group in the 2-isomer and ortho to the nitro group in the 3-isomer. The regiochemistry with respect to the trifluoromethyl group results in steric interactions that rotate the carboxylic acid group or the nitro group out of the aromatic plane in the 2- and 3-isomer, respectively. Each molecule engages in intermolecular hydrogen bonding, forming head-to-tail dimers with graph-set notation R 2 2(8) and donor–acceptor hydrogen-bonding distances of 2.7042 (14) Å in the 2-isomer and 2.6337 (16) in the 3-isomer. Recrystallization attempts did not yield untwinned crystals.

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32

Mladěnka, Přemysl, Jana Karlíčková, Marcel Hrubša, et al. "Interaction of 2,6,7-Trihydroxy-Xanthene-3-Ones with Iron and Copper, and Biological Effect of the Most Active Derivative on Breast Cancer Cells and Erythrocytes." Applied Sciences 10, no. 14 (2020): 4846. http://dx.doi.org/10.3390/app10144846.

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Metal chelators can be potentially employed in the treatment of various diseases, ranging from metal overload to neoplastic conditions. Some xanthene derivatives were previously reported to complex metals. Thus, in a search for a novel iron or copper chelator, a series of 9-(substituted phenyl)-2,6,7-trihydroxy-xanthene-3-ones was tested using a competitive spectrophotometric approach. The most promising compound was evaluated in biological models (breast adenocarcinoma cell lines and erythrocytes). In general, substitution of the benzene ring in position 9 had a relatively low effect on the chelation. Only the trifluoromethyl substitution resulted in stronger chelation, probably via a positive effect on solvation. All compounds chelated iron, but their copper-chelating effect was only minimal, since it was no longer observed under highly competitive conditions. Interestingly, all compounds reduced both iron and copper. Additional experiments showed that the trifluoromethyl derivative protected erythrocytes and even cancer cells against excess copper. In summary, the tested compounds are iron chelators, which are also capable of reducing iron/copper, but the copper-reducing effect is not associated with increased copper toxicity.

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33

Yoon, Goo, Seung Hoon Cheon, Jung Hyun Shim, and Seung Sik Cho. "Design and Evaluation of Licochalcone A Derivatives as Anticancer Agents." Natural Product Communications 13, no. 6 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300609.

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New derivatives of licochalcone A were synthesized and evaluated for their potential anticancer activities. Compounds 6 (( E)-N-(4-(3-(5-bromo-4-hydroxy-2-methoxy phenyl) acryloyl) phenyl)-4-isopropylbenzamide) and 8 (1-(3-dimethylamino-phenyl)-3-(2-trifluoromethyl-phenyl)-propenone) showed potent activity against the screened cancer cell lines with that of compound 6 ranging from 6.9 ± 0.2 μM to 22.9 ± 3.1 μM, and that of compound 8 from 4.2 ± 0.5 μM to 11.8 ± 0.7 μM. Both compounds showed stronger cytotoxicity than that of licochalcone A. These two candidates have very different substituents and could be considered as promising lead compounds for further development of potent anticancer agents.

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34

Nagai, Takabumi, Yoshihiro Nasu, Tetsuo Shimada, et al. "Diels-Alder reactions of trifluoromethyl dienes obtained from ene reactions of trifluoromethyl carbonyl compounds." Journal of Fluorine Chemistry 57, no. 1-3 (1992): 245–49. http://dx.doi.org/10.1016/s0022-1139(00)82837-7.

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35

Mendoza, Jose H. Quintana, J. A. Henao, Carlos E. Rondón Flórez, Carlos E. Puerto Galvis, and Vladimir V. Kouznetsov. "X-ray diffraction data of 4-phenyl-6-(trifluoromethyl)-3,4-dihydroquinolin-2(1H)-one and its synthetic precursor N-[4-(trifluoromethyl)phenyl]cinnamamide." Powder Diffraction 31, no. 3 (2016): 233–39. http://dx.doi.org/10.1017/s0885715616000282.

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The title compound, the 4-phenyl-6-(trifluoromethyl)-3,4-dihydroquinolin-2(1H)-one (4) with chemical formula: (C16H12F3NO), was synthesized from N-[4-(trifluoromethyl)phenyl]cinnamamide (3), chemical formula: (C16H12F3NO), through an intramolecular cyclization mediated by triflic acid. Preliminary molecular characterization of both compounds was performed by Fourier transform infrared spectroscopy, gas chromatography mass spectrometry, and nuclear magnetic resonance spectroscopy (1H, 13C); crystallographic characterization was completed by X-ray diffraction of polycrystalline samples. The title compound 4 crystallized in a monoclinic system and unit-cell parameters are reported [a = 16.002 (3), b = 5.170 (1), c = 17.733 (3) Å, β = 111.11 (2)°, unit-cell volume V = 1368.5 (3) Å3, Z = 4] P21/c (No. 14) space group; the title compound 3 crystallized in a monoclinic system and unit-cell parameters are reported [a = 12.902 (2), b = 5.144 (1), c = 20.513 (5) Å, β = 91.67 (2)°, unit-cell volume V = 1360.7 (4) Å3, Z = 4] P21/c (No. 14) space group.

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36

Krátký, Martin, Zsuzsa Baranyai, Šárka Štěpánková, et al. "N-Alkyl-2-[4-(trifluoromethyl)benzoyl]hydrazine-1-carboxamides and Their Analogues: Synthesis and Multitarget Biological Activity." Molecules 25, no. 10 (2020): 2268. http://dx.doi.org/10.3390/molecules25102268.

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Based on the isosterism concept, we have designed and synthesized homologous N-alkyl-2-[4-(trifluoromethyl)benzoyl]hydrazine-1-carboxamides (from C1 to C18) as potential antimicrobial agents and enzyme inhibitors. They were obtained from 4-(trifluoromethyl)benzohydrazide by three synthetic approaches and characterized by spectral methods. The derivatives were screened for their inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) via Ellman’s method. All the hydrazinecarboxamides revealed a moderate inhibition of both AChE and BuChE, with IC50 values of 27.04–106.75 µM and 58.01–277.48 µM, respectively. Some compounds exhibited lower IC50 for AChE than the clinically used drug rivastigmine. N-Tridecyl/pentadecyl-2-[4-(trifluoromethyl)benzoyl]hydrazine-1-carboxamides were identified as the most potent and selective inhibitors of AChE. For inhibition of BuChE, alkyl chain lengths from C5 to C7 are optimal substituents. Based on molecular docking study, the compounds may work as non-covalent inhibitors that are placed in a close proximity to the active site triad. The compounds were evaluated against Mycobacterium tuberculosis H37Rv and nontuberculous mycobacteria (M. avium, M. kansasii). Reflecting these results, we prepared additional analogues of the most active carboxamide (n-hexyl derivative 2f). N-Hexyl-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine (4) exhibited the lowest minimum inhibitory concentrations within this study (MIC ≥ 62.5 µM), however, this activity is mild. All the compounds avoided cytostatic properties on two eukaryotic cell lines (HepG2, MonoMac6).

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37

Petrov, Viacheslav A., and Will Marshall. "Reaction of 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithiethane with N-vinyl compounds." Beilstein Journal of Organic Chemistry 9 (November 21, 2013): 2615–19. http://dx.doi.org/10.3762/bjoc.9.295.

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The reaction of hexafluorothioacetone dimer (2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithiethane, 1) with vinylamides leads to the rapid formation of [2 + 2] cycloadducts: 4-amino-2,2-bis(trifluoromethyl)thietanes. The reaction proceeds in polar solvents (DMF, DMSO) in the absence of a catalyst at elevated temperature producing the corresponding cycloadducts in 47–86% yield. The reaction of N-vinylimidazole unexpectedly led to the formation of the corresponding 1-(hexafluoroisopropyl)-3-vinyl-1,3-dihydro-2H-imidazole-2-thione (5). The structure of this compound, along with the structures of two new thietanes was confirmed by single crystal X-ray diffraction.

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38

Pavlenko, Natalia V., Tatiana I. Oos, Yurii L. Yagupolskii, Igor I. Gerus, Uwe Doeller та Lothar Willms. "A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids". Beilstein Journal of Organic Chemistry 10 (26 березня 2014): 722–31. http://dx.doi.org/10.3762/bjoc.10.66.

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A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.

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39

Raveesha, Rajaiah, Malavalli Guruswamy Dileep Kumar, and Salekoppal Boregowda Benaka Prasad. "Synthesis of 3-Trifluoromethyl-5,6-dihydro-[1,2,4]triazolo Pyrazine Derivatives and Their Anti-Cancer Studies." Molbank 2020, no. 4 (2020): M1173. http://dx.doi.org/10.3390/m1173.

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The synthesis of a wide variety of 3-trifluoromethyl-5,6-dihydro-[1,2,4]triazolo pyrazine derivatives, by the treatment of 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride with an array of isocyanates in the presence of triethylamine, is reported. All the target compounds were synthesized in excellent yields under mild reaction conditions. The target molecules were effectively screened for their anti-cancer properties and the results are promising. The resultant compounds were assessed for their antiproliferative action against two human colon cancer cell lines (HCT-116 and HT-29 colon cancer cell lines). The IC50 range was estimated at 6.587 to 11.10 µM showing that compound RB7 had remarkable anticancer movement on HT-29. Additionally, it was discovered that RB7 incited the mitochondrial apoptotic pathway by up-regulating Bax and down-regulating Bcl2, eventually leading to the activation of Caspase 3 in HT-29 cells and initiation of cell death via the mitochondrial apoptotic pathway.

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40

Chambers, Richard D., Jock Moilliet, and Michael H. Rock. "The synthesis of bis(trifluoromethyl)aromatic compounds, Lausanne." Journal of Fluorine Chemistry 54, no. 1-3 (1991): 248. http://dx.doi.org/10.1016/s0022-1139(00)83758-6.

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41

Laurent, A., G. Alvernhe, I. Le Dréan, S. Lesniak, and A. Selmi. "Synthesis and specific reactivity of some trifluoromethyl compounds." Journal of Fluorine Chemistry 58, no. 2-3 (1992): 134. http://dx.doi.org/10.1016/s0022-1139(00)80581-3.

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42

Naumann, Dieter, Thomas Roy, and Frank Trinius. "On trifluoromethyl copper(III) and silver(III) compounds." Journal of Fluorine Chemistry 58, no. 2-3 (1992): 264. http://dx.doi.org/10.1016/s0022-1139(00)80718-6.

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43

Ghiazza, Clément, Thierry Billard, and Anis Tlili. "Trifluoromethyl- and Fluoroalkylselenolations of Alkynyl Copper(I) Compounds." Chemistry - A European Journal 23, no. 42 (2017): 10013–16. http://dx.doi.org/10.1002/chem.201702028.

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44

NAGAI, T., and I. KUMADAKI. "ChemInform Abstract: Ene Reaction of Trifluoromethyl Carbonyl Compounds." ChemInform 23, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199201346.

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45

Lagu, Surendra Babu, Rajendra Prasad Yejella, Richie R. Bhandare, and Afzal B. Shaik. "Design, Synthesis, and Antibacterial and Antifungal Activities of Novel Trifluoromethyl and Trifluoromethoxy Substituted Chalcone Derivatives." Pharmaceuticals 13, no. 11 (2020): 375. http://dx.doi.org/10.3390/ph13110375.

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Despite the availability of many drugs to treat infectious diseases, the problems like narrow antimicrobial spectrum, drug resistance, hypersensitivities and systemic toxicities are hampering their clinical utility. Based on the above facts, in the present study, we designed, synthesized and evaluated the antibacterial and antifungal activity of novel fluorinated compounds comprising of chalcones bearing trifluoromethyl (A1–A10) and trifluoromethoxy (B1–B10) substituents. The compounds were characterized by spectroscopic techniques and evaluated for their antimicrobial activity against four pathogenic Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Escherichia coli and Bacillus subtilis) bacterial and fungal (Candida albicans and Aspergillus niger) strains. In this study, the compounds with trifluoromethoxy group were more effective than those with trifluoromethyl group. Among the 20 fluorinated chalcones, compound A3/B3 bearing an indole ring attached to the olefinic carbon have been proved to possess the most antimicrobial activity compared to the standard drugs without showing cytotoxicity on human normal liver cell line (L02). Further, the minimum inhibitory concentration (MIC) for A3/B3 was determined by serial tube dilution method and showed potential activity. These results would provide promising access to future study about the development of novel agents against bacterial and fungal infections.

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46

Izquierdo, Javier, Atul Jain, Sarki Abdulkadir, and Gary Schiltz. "Palladium-Catalyzed Coupling Reactions on Functionalized 2-Trifluoromethyl-4-chromenone Scaffolds: Synthesis of Highly Functionalized Trifluoromethyl Heterocycles." Synthesis 51, no. 06 (2018): 1342–52. http://dx.doi.org/10.1055/s-0037-1610669.

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The chromenone core is an ubiquitous group in biologically active natural products and has been extensively used in organic synthesis. Fluorine-derived compounds, including those with a trifluoromethyl group (CF3), have shown enhanced biological activities in numerous pharmaceuticals compared with their non-fluorinated analogues. 2-Trifluoromethylchromenones can be readily functionalized at the 8- and 7-positions, providing chromenones cores of high structural complexity, which are excellent precursors for numerous trifluoromethyl heterocycles.

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47

Tyrra, Wieland, and Dieter Naumann. "Polar trifluoromethylation reactions: the formation of bis(trifluoromethyl)iodine(III) compounds and trifluoromethyl iodine(III) cations and anions." Canadian Journal of Chemistry 69, no. 2 (1991): 327–33. http://dx.doi.org/10.1139/v91-050.

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IX3 (X = Cl, OCOCF3, ONO2) reacts with Cd(CF3)2 complexes or Bi(CF3)3 to yield the corresponding CF3IX2 derivatives. 19F nuclear magnetic resonance spectroscopic evidence is found for [I(CF3)2]+ and I(CF3)2X (X = Cl, OCOCF3) in the reactions of CF3IX2 with Cd(CF3)2 complexes. During the reaction of CF3IF2 and Hg(CF3)2 the new species I(CF3)2F and cis-[I(CF3)2F2]− are identified by nuclear magnetic resonance spectroscopy. The reactions proceed under polar conditions and can be accelerated by the addition of a Lewis acid such as BF3, B(OCOCF3)3, or Sb(V) compounds. Difluoromethyl compounds are formed as by-products. Key words: polar trifluoromethylations, trifluoromethyl iodine(III) compounds, difluoromethyl group formation.

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48

Lapsheva, Ekaterina N., Thibault Cheisson, Carlos Álvarez Lamsfus, et al. "Reactivity of Ce(iv) imido compounds with heteroallenes." Chemical Communications 56, no. 35 (2020): 4781–84. http://dx.doi.org/10.1039/c9cc10052k.

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The reactivity of alkali metal capped Ce(iv) imido compounds [M(DME)2][CeNArF(TriNOx)] (1-M with M = K, Rb, Cs and ArF = 3,5-bis(trifluoromethyl)phenyl) with CO2 and organic isocyanates has been evaluated.

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49

Mondal, Pradip Kumar, Rahul Shukla, Subha Biswas, and Deepak Chopra. "Role of halogen-involved intermolecular interactions and existence of isostructurality in the crystal packing of —CF3 and halogen (Cl or Br or I) substituted benzamides." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 74, no. 6 (2018): 574–91. http://dx.doi.org/10.1107/s2052520618013422.

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A total of 23 benzamides are obtained through a simple reaction between chloro-/bromo-/iodoaniline and trifluoromethylbenzoyl chloride and characterized using single-crystal X-ray diffraction. Crystal structures of three series of benzamides based on N-chlorophenyl–trifluoromethyl–benzamide (nine compounds), N-bromophenyl–trifluoromethyl–benzamide (six compounds), and N-iodophenyl–trifluoromethyl–benzamide (eight compounds) are prepared to analyse the halogen-mediated noncovalent interactions. The influences of Cl/Br/I and trifluoromethyl substituents on the respective interactions are examined in the presence of a strong N—H...O hydrogen bond. This exercise has resulted in the documentation of frequently occurring supramolecular synthons involving halogen atoms in the crystal packing of benzamide molecules in the solid state. In the present study, a detailed quantitative evaluation has been performed on the nature, energetics, electrostatic contributions, and topological properties of short and directional intermolecular interactions derived from the electron density on halogenated benzamides in the solid state. Besides these, the occurrence of three-, two- and one-dimensional isostructurality in halogen (Cl or Br or I) substituted benzamide analogues is also investigated. A `region of co-existence' involving halogen-based intermolecular interactions in the vicinity of the sum of the van der Waals radii has been identified. Thus, the nature of the halogen (effective size), type of interaction and the packing characteristics via presence of additional interactions establish the subtle, yet important, role of cooperativity in intermolecular interactions in crystal packing.

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Ma, Xingxing, and Qiuling Song. "Recent progress on selective deconstructive modes of halodifluoromethyl and trifluoromethyl-containing reagents." Chemical Society Reviews 49, no. 24 (2020): 9197–219. http://dx.doi.org/10.1039/d0cs00604a.

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Journal articles on the topic 'Trifluoromethyl compounds'

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