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An Efficient Synthesis of Fused 2‐Aryliminothiazolines via a Solvent‐Free Cyclopropyliminium Rearrangement
Author(s) -
Samet Alexander V.,
Silyanova Evgenia A.,
Semenova Mari.,
Karnoukhova Valentina A.,
Semenov Victor V.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600453
Subject(s) - solvent , chemistry , base (topology) , ring (chemistry) , antimitotic agent , stereochemistry , sea urchin , combinatorial chemistry , tubulin , organic chemistry , biology , mathematics , microtubule , microbiology and biotechnology , mathematical analysis
( Z )‐3‐Aryliminopyrrolo[ 1,2‐c ]thiazoles were prepared by a base‐induced dehydrobromination of 3‐arylaminopyrrolo[ 1,2‐c ]thiazolium bromides, which, in turn, were obtained via an efficient solvent‐free cyclopropyliminium rearrangement of the corresponding 4‐cyclopropylthiazole hydrobromides proceeding in melt at high rate and in excellent yields. Biological evaluation using phenotypic sea urchin embryo assay showed that 2‐arylamino‐4‐cyclopropylthiazoles displayed an antimitotic tubulin‐unrelated activity, whereas fused‐ring rearrangement products were proposed to inhibit Ca‐Zn–dependent metalloproteases.