Literature DB >> 2318312

aS,7S-absolute configuration of natural (-)-colchicine and allo-congeners.

A Brossi1, O Boyé, A Muzaffar, H J Yeh, V Toome, B Wegrzynski, C George.   

Abstract

The aS,7S-absolute configuration of (-)-colchicine (1) and (-)-N-acetylcolchinol methyl ether (3, NCME) suggested on the basis of 1H NMR data and negative Cotton effects at about 260 nm (EtOH) is firmly established by an X-ray analysis of urea 5, a compound derived from 3. Binding of these compounds to tubulin requires an aS-configuration of the biaryl system.

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Year:  1990        PMID: 2318312     DOI: 10.1016/0014-5793(90)80139-a

Source DB:  PubMed          Journal:  FEBS Lett        ISSN: 0014-5793            Impact factor:   4.124


  2 in total

1.  Synthesis and biological activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride as potent cytotoxic antitubulin agents.

Authors:  Aleem Gangjee; Ying Zhao; Ernest Hamel; Cara Westbrook; Susan L Mooberry
Journal:  J Med Chem       Date:  2011-08-05       Impact factor: 7.446

2.  NMR and DFT investigations of structure of colchicine in various solvents including density functional theory calculations.

Authors:  Gregory K Pierens; T K Venkatachalam; David C Reutens
Journal:  Sci Rep       Date:  2017-07-17       Impact factor: 4.379

  2 in total

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