87736-83-2Relevant academic research and scientific papers
Ammonia-free synthesis of 3-trifluoromethyl-3-phenyldiaziridine
Kumar, Arun Babu,Manetsch, Roman
, p. 626 - 631 (2018/02/26)
An ammonia-free synthesis of 3-trifluoromethyl-3-phenyldiaziridine, an important intermediate in the synthesis of a widely used photolabel 3-trifluoromethyl-3-phenyldiazirine, is described. By avoiding the use of volatile, corrosive, and toxic anhydrous ammonia, the major hazard involved in the synthesis of this widely used photolabel is eliminated. Furthermore, this synthesis is convenient compared to the conventional route, since it is significantly less time consuming and, due to the absence of liquid ammonia, this method does not require the maintenance of low temperature for prolonged periods.
Diazirine-containing RNA photo-cross-linking probes for capturing microRNA targets
Nakamoto, Kosuke,Ueno, Yoshihito
, p. 2463 - 2472 (2014/04/17)
Here, we report the applicability of diazirine-containing RNA photo-cross-linking probes for the identification of microRNA (miRNA) targets. The RNA cross-linking probes were synthesized by substituting the RNA nucleobases with nucleoside analogues such as 1-O-[3-(3-trifluoromethyl-3H- diazirin-3-yl)]benzyl-β-d-ribofuranose or 1-O-[4-(3-trifluoromethyl-3H- diazirin-3-yl)]benzyl-β-d-ribofuranose that carry aryl trifluoromethyl diazirine moieties. The probes were successfully cross-linked with synthetic RNAs containing the four natural nucleosides on the opposite site of the nucleoside analogues. Furthermore, it was found that miRNAs containing these analogues were effective in regulating the expression of their target genes. Thus, RNAs containing the nucleoside analogues are promising candidates as photo-cross-linking probes to identify the target mRNAs of miRNAs.
NOVEL N-BENZYLAMIDE SUBSTITUTED DERIVATIVES OF 2-(ACYLAMIDO)ACETIC ACID AND 2-(ACYLAMIDO)PROPIONIC ACIDS: POTENT NEUROLOGICAL AGENTS
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Page/Page column 62; 64, (2009/12/27)
A first aspect of the invention is a compound (sometimes also referred to herein as an "active agent" or "active compound") of Formula (I) or ( Ia): or a pharmaceutically acceptable salt or prodrug thereof. Compositions thereof and methods of using the same (e.g. for the treatment of a neurological disease) are also described.
Trifluoromethyldiazirine: An effective photo-induced cross-linking probe for exploring amyloid formation
Smith, David P.,Anderson, Jon,Plante, Jeffrey,Ashcroft, Alison E.,Radford, Sheena E.,Wilson, Andrew J.,Parker, Martin J.
supporting information; experimental part, p. 5728 - 5730 (2009/04/13)
The separative and analytical power of ion mobility spectrometry-mass spectrometry combined with photo-induced cross-linking of site-specifically incorporated trifluoromethyldiazirine provides a powerful approach towards structural characterisation of amy
Swern Oxidation of Diaziridines to Diazirines
Richardson, Stewart K.,Ife, Robert J.
, p. 1172 - 1174 (2007/10/02)
The trifluoromethyldiaziridines (1) - (6) have been converted into the photolabile diazirines (7) - (12) using dimethyl sulphoxide-oxalyl chloride; several of these diazirines have previously been used as intermediates in the preparation of photoaffinity
4-(1-Azi-2,2,2-trifluoroethyl)benzoic Acid, a Highly Photolabile Carbene Generating Label Readily Fixable to Biochemical Agents
Nassal, Michael
, p. 1510 - 1523 (2007/10/02)
The title compound is synthesized starting from either 4-bromobenzyl tert butyldimethylsilyl ether (5b) or 4-bromobenzyl tert-butyl ether (5c) or - most simply - from 4-bromotoluene (5a).In the first step Br was replaced by Li using n-butyllithium, then the organometallic compounds were converted into the respective trifluoroacetophenones 6a - c with N-trifluoroacetylpiperidine.The azi moiety (diazirine) was prepared from the oximes 7a - c via O-tosyloximes 8a - c plus ammonia yielding the diaziridines 9a - c and oxidation of the latter with Ag2O.Oxidation by permanganate - of the ethers after acidic cleavage - yields the title compound 12.On irradation (λ > 300 nm) 12 by elimination of N2 with a half-life period of 22 s generates the corresponding carbene.At the same time from 12 with ca. 20percent the yellow isomeric 4-(1-diazo-2,2,2-trifluoroethyl)benzoic acid (20) is formed which is photolyzed generating the same carbene as 12.The synthesis of 20 is described starting from 4-bromobenzaldehyde. - The diazirine 12 as its N-hydroxysuccinimide ester 13, or using other methods of amide synthesis, can readily be coupled to amino functions of biochemically interesting agents thus forming photoaffinity labels.
