Comprehensive Synthesis of Photoreactive (3-Trifluoromethyl)diazirinyl Indole Derivatives from 5- and 6- Trifluoroacetylindoles for Photoaffinity Labeling

5- and 6-trifluoromethyldiazirinyl indoles were synthesized from corresponding bromoindole derivatives for the first time. They acted as mother skeletons for the comprehensive synthesis of various bioactive indole metabolites. These can be used in biological functional analysis as diazirine-based ph...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-10, Vol.77 (19), p.8581-8587
Main Authors: Murai, Yuta, Masuda, Katsuyoshi, Sakihama, Yasuko, Hashidoko, Yasuyuki, Hatanaka, Yasumaru, Hashimoto, Makoto
Format: Article
Language:English
Subjects:
Chemistry
Diazomethane - analogs & derivatives
Diazomethane - chemistry
Diazomethane - metabolism
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organic chemistry
Photoaffinity Labels - chemical synthesis
Photoaffinity Labels - chemistry
Photoaffinity Labels - metabolism
Photochemistry
Preparations and properties
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Summary:5- and 6-trifluoromethyldiazirinyl indoles were synthesized from corresponding bromoindole derivatives for the first time. They acted as mother skeletons for the comprehensive synthesis of various bioactive indole metabolites. These can be used in biological functional analysis as diazirine-based photoaffinity labels.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301552m