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Abstract
Combretastatin A-4 (CA-4) is a natural product, which consists of two phenyl rings, linked by an ethylene bridge. CA-4, inhibitor of polymerization of tubulin to microtubules, possesses a strong antitumor and anti-vascular properties both in vitro and in vivo. Previous studies showed that disodium phosphate salt of CA-4, a water-soluble prodrug is well tolerated at therapeutically useful doses. However, it should be noted that the cis-configuration of the double bond and the 3,4,5-trimethoxy group on ring A is necessary for the biological activity of CA-4. Structure of CA-4 renders the compound readily susceptible to isomerization, which reduces the potency and bioavailability. To circumvent this problem, a lot of scientists in the world synthesized a series of cis-restricted CA-4 analogs, where the double bond has been replaced by introduction of non-heterocyclic groups or heterocyclic groups like β-lactam and oxadiazole. This paper reviews the most important approaches in analogs of combretastatin synthesis and presents structure-reactivity relationships for these compounds.
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- Publication version
- Accepted or Published Version
- DOI:
- Digital Object Identifier (open in new tab) 10.2174/1871520616666160204111832
- License
- Copyright (2016 Bentham Science Publishers)
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
Anti-Cancer Agents in Medicinal Chemistry
no. 16,
edition 8,
pages 942 - 960,
ISSN: 1871-5206 - Language:
- English
- Publication year:
- 2016
- Bibliographic description:
- Siebert A., Gensicka-Kowalewska M., Cholewiński G., Dzierzbicka K.: Synthesis of Combretastatin A-4 Analogs and their Biological Activities// Anti-Cancer Agents in Medicinal Chemistry. -Vol. 16, iss. 8 (2016), s.942-960
- DOI:
- Digital Object Identifier (open in new tab) 10.2174/1871520616666160204111832
- Verified by:
- Gdańsk University of Technology
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