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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

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  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]
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  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]
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