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Journal articles on the topic 'Trifluoromethyl compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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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,

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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

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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

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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—

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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

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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 int

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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 carbothiami

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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 pathol

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11

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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13

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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14

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, h

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15

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 m

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16

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 anal

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17

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-(trifluo

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18

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 physi

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19

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-lif

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20

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 chlor

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21

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 measur

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22

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

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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(trifluoro

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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’ pane

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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. Ti

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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 dim

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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 c

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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

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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 titl

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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 a

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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

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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

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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

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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 pa

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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 f

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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)<sub>2</sub>][CeNAr<sup>F</sup>(TriNOx)] (1-M with M = K, Rb, Cs and Ar<sup>F</sup> = 3,5-bis(trifluoromethyl)phenyl) with CO<sub>2</sub> 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 examine

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50

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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