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Chemical Compound Review

AC1L3ARL     trifluoromethane

Synonyms: 2264-21-3, Trifluoromethyl radical
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Disease relevance of trifluoromethane


High impact information on trifluoromethane


Chemical compound and disease context of trifluoromethane


Biological context of trifluoromethane

  • In the current study, analogs of anandamide representing three classes of putative transition-state inhibitor (trifluoromethyl ketones, alpha-keto esters, and alpha-keto amides) were synthesized and tested as inhibitors of anandamide hydrolysis in vitro and as ligands for CBR1 [12].
  • Aryl, trifluoromethyl alkyl, and alpha,beta-unsaturated ketimines engage in regioselective aryl-nitrogen bond formation via 5-exo cyclizations of an aryl radical to azomethine nitrogen [13].
  • Further, in order to determine the active site binding orientation of beta-phenylethylamines bearing aryl lipophilic substituents, the aryl trifluoromethyl-substituted derivatives of 12 and 13 (20-27), as well as anti-9-amino-5-(trifluoromethyl)-(18) and anti-9-amino-6-(trifluoromethyl) benzonorbornene (19), were prepared and evaluated [14].
  • We have initiated a structure-activity relationship study of the replacement of the methyl group on the carbon bridge between the naphthalene and imidazole rings of 2 with a hydrogen, hydroxy, methoxy, carbonyl, or trifluoromethyl group and compared their biological activities with medetomidine 1 and the optical isomers of 2 [15].
  • The trifluoromethyl group allows the bound environment and bound to free exchange kinetics of this alcohol to be examined by using 19F NMR [16].

Anatomical context of trifluoromethane


Associations of trifluoromethane with other chemical compounds

  • In contrast, the bromelain-derived ectodomain of HA was labeled by 1-palmitoyl-2(11-[4-[3-(trifluoromethyl)diazirinyl]phenyl]- [2-3H]undecanoyl)-sn-glycerol-3-phosphocholine at low pH but not by diphosphatidylethanolamine trifluoromethyl [3H]phenyl diazirine [21].
  • With the exception of retinol and the trifluoromethyl nonyloxyphenyl analog of RA, the ability of the retinoids to induce RAR beta mRNA and their growth inhibitory effect were correlated [22].
  • The presence of a trifluoromethyl rather than a methyl substituent in the bay-region greatly decreases the DNA-binding and tumour-initiating activity of the cyclopenta[alpha]phenanthren-17-ones [23].
  • In both complexes, the trifluoromethyl group is partially immobilized, but differences are observed in the degree of interaction of fluorine atoms with the active-site His 57 imidazole ring, with amide nitrogen NH 193, and with other portions of the inhibitor molecule [24].
  • The search for a radioiodinated AR ligand prompted us to synthesize 4-[4, 4-dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-i odo benzonitrile (DTIB) wherein the trifluoromethyl group of RU 59063 was substituted with the similarly hydrophobic iodine atom [25].

Gene context of trifluoromethane

  • Replacement of the potentially labile hydroxamic acid moiety with a trifluoromethyl ketone or a ketooxazole gave measurable HDAC potency but only modest cellular and in vivo activity [26].
  • The stimulation of AA release induced by ET-1 was prevented by arachydonyl trifluoromethyl ketone (AACOCF3), a selective inhibitor of cPLA2 and not by RHC80267, a diacylglycerol lipase inhibitor [27].
  • Celecoxib completely fills the entire CA II active site, with its trifluoromethyl group in the hydrophobic part of the active site and the p-tolyl moiety in the hydrophilic one, not establishing any interaction with Phe131 [28].
  • According to docking studies, these molecules appear to bind the COX-2 binding site differently than indomethacin, with the insertion of the substituent at the 2-position in the hydrophobic pocket of the enzyme and the 1-position phenyl ring in the trifluoromethyl zone [29].
  • On the other hand, trifluoromethyl substituents at the 3'- and 5'-positions (27) essentially abolished binding affinity at beta 2-AR and TP receptors [30].

Analytical, diagnostic and therapeutic context of trifluoromethane


  1. Homeodomain-interacting protein kinase-2 restrains cytosolic phospholipase A2-dependent prostaglandin E2 generation in human colorectal cancer cells. D'Orazi, G., Sciulli, M.G., Di Stefano, V., Riccioni, S., Frattini, M., Falcioni, R., Bertario, L., Sacchi, A., Patrignani, P. Clin. Cancer Res. (2006) [Pubmed]
  2. The toxicity of thioxanthene neuroleptics to isolated rat liver cells. Abernathy, C.O., Zimmerman, H.J. Proc. Soc. Exp. Biol. Med. (1975) [Pubmed]
  3. Enantioselective reduction of trifluoromethyl ketones with chiral organomagnesium amides (COMAs). Yong, K.H., Chong, J.M. Org. Lett. (2002) [Pubmed]
  4. Anhydrodihydroartemisinin and its 10-trifluoromethyl analogue: access to novel d-ring-contracted artemisinin trifluoromethyl ketones. Grellepois, F., Chorki, F., Crousse, B., Ourévitch, M., Bonnet-Delpon, D., Bégué, J.P. J. Org. Chem. (2002) [Pubmed]
  5. Analogues of key precursors of aspartyl protease inhibitors: synthesis of trifluoromethyl amino epoxides. Tam, N.T., Magueur, G., Ourévitch, M., Crousse, B., Bégué, J.P., Bonnet-Delpon, D. J. Org. Chem. (2005) [Pubmed]
  6. Fractionation factors and activation energies for exchange of the low barrier hydrogen bonding proton in peptidyl trifluoromethyl ketone complexes of chymotrypsin. Lin, J., Westler, W.M., Cleland, W.W., Markley, J.L., Frey, P.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  7. Nitroaniline diamine.poly(dA-dT) complexes: 1H and 19F NMR parameters for full intercalation of aromatic rings into DNA. Patel, D.J., Gabbay, E.J. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  8. Epstein-Barr virus modulates 5-lipoxygenase product synthesis in human peripheral blood mononuclear cells. Gosselin, J., Borgeat, P. Blood (1997) [Pubmed]
  9. Willardiines differentiate agonist binding sites for kainate- versus AMPA-preferring glutamate receptors in DRG and hippocampal neurons. Wong, L.A., Mayer, M.L., Jane, D.E., Watkins, J.C. J. Neurosci. (1994) [Pubmed]
  10. Selective inhibitors of cytosolic or secretory phospholipase A2 block TNF-induced activation of transcription factor nuclear factor-kappa B and expression of ICAM-1. Thommesen, L., Sjursen, W., Gåsvik, K., Hanssen, W., Brekke, O.L., Skattebøl, L., Holmeide, A.K., Espevik, T., Johansen, B., Laegreid, A. J. Immunol. (1998) [Pubmed]
  11. Role of glucuronide formation in the selective toxicity of 3-trifluoromethyl-4-nitrophenol (TFM) for the sea lamprey: comparative aspects of TFM uptake and conjugation in sea lamprey and rainbow trout. Lech, J.J., Statham, C.N. Toxicol. Appl. Pharmacol. (1975) [Pubmed]
  12. Inhibitors of arachidonoyl ethanolamide hydrolysis. Koutek, B., Prestwich, G.D., Howlett, A.C., Chin, S.A., Salehani, D., Akhavan, N., Deutsch, D.G. J. Biol. Chem. (1994) [Pubmed]
  13. Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline alpha-amino acid synthesis. Viswanathan, R., Prabhakaran, E.N., Plotkin, M.A., Johnston, J.N. J. Am. Chem. Soc. (2003) [Pubmed]
  14. Binding orientation of amphetamine and norfenfluramine analogues in the benzonorbornene and benzobicyclo[3.2.1]octane ring systems at the active site of phenylethanolamine N-methyltransferase (PNMT). Grunewald, G.L., Markovich, K.M., Sall, D.J. J. Med. Chem. (1987) [Pubmed]
  15. A structure-activity relationship study of benzylic modifications of 4-[1-(1-naphthyl)ethyl]-1H-imidazoles on alpha 1- and alpha 2-adrenergic receptors. Hong, S.S., Romstedt, K.J., Feller, D.R., Hsu, F.L., Cupps, T.L., Lyon, R.A., Miller, D.D. J. Med. Chem. (1994) [Pubmed]
  16. Fluorinated ligands as nuclear magnetic resonance probes of active-site nonequivalence in abortive ternary complexes of horse liver alcohol dehydrogenase. Anderson, D.C., Wilson, M.L., Dahlquist, F.W. Biochemistry (1982) [Pubmed]
  17. Cardioselective antiischemic ATP-sensitive potassium channel openers. 2. Structure-activity studies on benzopyranylcyanoguanidines: modification of the benzopyran ring. Atwal, K.S., Grover, G.J., Ferrara, F.N., Ahmed, S.Z., Sleph, P.G., Dzwonczyk, S., Normandin, D.E. J. Med. Chem. (1995) [Pubmed]
  18. The in vitro antitumor assay of "half-mustard type" phenothiazines in screens of AIDS-related leukemia and lymphomas. Wuonola, M.A., Palfreyman, M.G., Motohashi, N., Kawase, M., Gabay, S., Molnár, J. Anticancer Res. (1997) [Pubmed]
  19. 2-(4-Pyridyl)-delta 2-1,3,4-oxadiazolines from isonicotinoylhydrazones and diazomethane as potential antimycobacterial and anti-HIV agents. V. Vigorita, M.G., Ottanà, R., Zappalà, C., Maccari, R., Pizzimenti, F.C., Gabbrielli, G. Farmaco (1995) [Pubmed]
  20. Sister chromatid exchange induced by anti-herpes drugs. Cassiman, J.J., De Clercq, E., Jones, A.S., Walker, R.T., Van den Berghe, H. British medical journal (Clinical research ed.) (1981) [Pubmed]
  21. The HA2 subunit of influenza hemagglutinin inserts into the target membrane prior to fusion. Stegmann, T., Delfino, J.M., Richards, F.M., Helenius, A. J. Biol. Chem. (1991) [Pubmed]
  22. Modulation by retinoids of mRNA levels for nuclear retinoic acid receptors in murine melanoma cells. Clifford, J.L., Petkovich, M., Chambon, P., Lotan, R. Mol. Endocrinol. (1990) [Pubmed]
  23. The presence of a trifluoromethyl rather than a methyl substituent in the bay-region greatly decreases the DNA-binding and tumour-initiating activity of the cyclopenta[alpha]phenanthren-17-ones. Boyd, G.W., Coombs, M.M., Baird, W.M. Carcinogenesis (1995) [Pubmed]
  24. Structure of chymotrypsin-trifluoromethyl ketone inhibitor complexes: comparison of slowly and rapidly equilibrating inhibitors. Brady, K., Wei, A.Z., Ringe, D., Abeles, R.H. Biochemistry (1990) [Pubmed]
  25. Design, synthesis, and pharmacological characterization of 4-[4, 4-dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]- 2-iodobenzonitrile as a high-affinity nonsteroidal androgen receptor ligand. Van Dort, M.E., Robins, D.M., Wayburn, B. J. Med. Chem. (2000) [Pubmed]
  26. Histone deacetylase inhibitors: the Abbott experience. Curtin, M., Glaser, K. Current medicinal chemistry. (2003) [Pubmed]
  27. Endothelin-1-induced arachidonic acid release by cytosolic phospholipase A2 activation in rat vascular smooth muscle via extracellular signal-regulated kinases pathway. Trevisi, L., Bova, S., Cargnelli, G., Ceolotto, G., Luciani, S. Biochem. Pharmacol. (2002) [Pubmed]
  28. Carbonic anhydrase inhibitors: Valdecoxib binds to a different active site region of the human isoform II as compared to the structurally related cyclooxygenase II "selective" inhibitor celecoxib. Di Fiore, A., Pedone, C., D'Ambrosio, K., Scozzafava, A., De Simone, G., Supuran, C.T. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  29. Design, Syntheses, Biological Evaluation, and Docking Studies of 2-Substituted 5-Methylsulfonyl-1-Phenyl-1H-Indoles: Potent and Selective in vitro Cyclooxygenase-2 Inhibitors. Cruz-L??pez, O., D??az-Moch??n, J.J., Campos, J.M., Entrena, A., N????ez, M.T., Labeaga, L., Orjales, A., Gallo, M.A., Espinosa, A. ChemMedChem (2007) [Pubmed]
  30. Iodinated analogs of trimetoquinol as highly potent and selective beta 2-adrenoceptor ligands. De Los Angeles, J.E., Nikulin, V.I., Shams, G., Konkar, A.A., Mehta, R., Feller, D.R., Miller, D.D. J. Med. Chem. (1996) [Pubmed]
  31. Dissociation of carbanions from acyl iridium compounds: an experimental and computational investigation. Cordaro, J.G., Bergman, R.G. J. Am. Chem. Soc. (2004) [Pubmed]
  32. Correlation of low-barrier hydrogen bonding and oxyanion binding in transition state analogue complexes of chymotrypsin. Neidhart, D., Wei, Y., Cassidy, C., Lin, J., Cleland, W.W., Frey, P.A. Biochemistry (2001) [Pubmed]
  33. Aspartate 74 as a primary determinant in acetylcholinesterase governing specificity to cationic organophosphonates. Hosea, N.A., Radić, Z., Tsigelny, I., Berman, H.A., Quinn, D.M., Taylor, P. Biochemistry (1996) [Pubmed]
  34. Nonpeptidic inhibitors of human leukocyte elastase. 5. Design, synthesis, and X-ray crystallography of a series of orally active 5-aminopyrimidin-6-one-containing trifluoromethyl ketones. Veale, C.A., Bernstein, P.R., Bryant, C., Ceccarelli, C., Damewood, J.R., Earley, R., Feeney, S.W., Gomes, B., Kosmider, B.J., Steelman, G.B. J. Med. Chem. (1995) [Pubmed]
  35. Photodynamic studies and photoinactivation of Escherichia coli using meso-substituted cationic porphyrin derivatives with asymmetric charge distribution. Lazzeri, D., Rovera, M., Pascual, L., Durantini, E.N. Photochem. Photobiol. (2004) [Pubmed]
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