Recent developments on (−)-colchicine derivatives: Synthesis and structure-activity relationship

Abdullah A. Ghawanmeh, Hussein M. Al-Bajalan, Mukram Mohamed Mackeen, Feras Q. Alali, Kwok Feng Chong

Research output: Contribution to journalReview article

Abstract

(−)-Colchicine, an anti-microtubulin polymerization agent, is a valuable medication and the drug of choice for gout, Behçet's disease and familial Mediterranean fever. It has a narrow therapeutic index due to its high toxicity towards normal cells. Nonetheless, numerous (−)-colchicine derivatives have been synthesized and studied for their structure-activity relationship and preferential toxicity. Different functional groups such as amides, thioamides, N-arylurea and 8,12-diene cyclic have been incorporated into (−)-colchicine, resulting in derivatives (with moieties) that include electron-withdrawing and electron-donating groups. This review article focuses on recent developments in the chemical synthesis of (−)-colchicine derivatives, the substituents used, the functional groups linked to the substituents, the moieties and biological studies. Moreover, the current classification of derivatives based on the (−)-colchicine rings, namely ring A, B, and C (−)-colchicine derivatives, is discussed. This work demonstrates and summarizes the significance of (−)-colchicine derivatives in the biological field, and discusses their promising therapeutics for the future.

Original languageEnglish
Article number111788
JournalEuropean Journal of Medicinal Chemistry
Volume185
DOIs
Publication statusPublished - 1 Jan 2020

Fingerprint

Colchicine
Structure-Activity Relationship
Derivatives
Functional groups
Toxicity
Thioamides
Electrons
Familial Mediterranean Fever
Behcet Syndrome
Gout
Amides
Polymerization
Therapeutics
Pharmaceutical Preparations

Keywords

  • (−)-Colchicine
  • (−)-Colchicine derivatives
  • Structure-activity relationship

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Recent developments on (−)-colchicine derivatives : Synthesis and structure-activity relationship. / Ghawanmeh, Abdullah A.; Al-Bajalan, Hussein M.; Mackeen, Mukram Mohamed; Alali, Feras Q.; Chong, Kwok Feng.

In: European Journal of Medicinal Chemistry, Vol. 185, 111788, 01.01.2020.

Research output: Contribution to journalReview article

Ghawanmeh, Abdullah A. ; Al-Bajalan, Hussein M. ; Mackeen, Mukram Mohamed ; Alali, Feras Q. ; Chong, Kwok Feng. / Recent developments on (−)-colchicine derivatives : Synthesis and structure-activity relationship. In: European Journal of Medicinal Chemistry. 2020 ; Vol. 185.
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