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Deaminocolchinyl Methyl Ether: Synthesis from 2,3,4,4′‐Tetramethoxybiphenyl‐2‐carbaldehyde. Comparison of antitubulin effects of deaminocolchinyl methyl ether and dehydro analogs
Author(s) -
Boyé Olivier,
Itoh Yoshikuni,
Brossi Arnold
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720805
Subject(s) - chemistry , congener , ether , ketone , biphenyl , aldehyde , stereochemistry , methyl ketone , tricyclic , organic chemistry , catalysis
Synthesis of deaminocolchinyl methyl ether 9 was achieved from tetramethoxy‐substituted biphenyl‐2‐carb‐aldehyde 12 via tricyclic ketone 20 and 5,6‐didehydro congener 11 . Compound 9 was identical in every respect with material prepared from colchicine via 6,7‐didehydro congener 10 . Measuring inhibition of tubulin polymerization in vitro showed compounds 4 , 5 , and 9 – 11 of the alloseries of colchicinoids to be particularly potent inhibitors.