The effect of vindoline C-16 substituents on the biomimetic coupling reaction: Synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues

Bioorganic & Medicinal Chemistry Letters
2012.0

Abstract

A new series of vinorelbine analogues are designed and synthesized to explore the vindoline C-16 substituent effects on the biomimetic coupling with catharanthine, and the structure-activity relationships of these vinorelbine analogues as cytotoxic agents are also studied. The results show that introduction of severe steric hindrance and/or electron-withdrawing group at C-16 site are not propitious to improving the yields of the coupling reaction, and the SAR information collected so far suggests that small alkyl groups substituted at C-16 of vindoline are conductive to maintaining the cytotoxicity.

Knowledge Graph

Similar Paper

The effect of vindoline C-16 substituents on the biomimetic coupling reaction: Synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues
Bioorganic & Medicinal Chemistry Letters 2012.0
Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: Preparation and evaluation of a key series of vinblastine analogues
Bioorganic & Medicinal Chemistry Letters 2010.0
10′-Fluorovinblastine and 10′-Fluorovincristine: Synthesis of a Key Series of Modified Vinca Alkaloids
ACS Medicinal Chemistry Letters 2011.0
Synthesis and structure–activity relationship studies of cytotoxic vinorelbine amide analogues
Bioorganic & Medicinal Chemistry Letters 2012.0
Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs
Bioorganic & Medicinal Chemistry Letters 2012.0
Total Synthesis and Evaluation of Vinblastine Analogues Containing Systematic Deep-Seated Modifications in the Vindoline Subunit Ring System: Core Redesign
Journal of Medicinal Chemistry 2013.0
Structure-activity relationships of dimeric Catharanthus alkaloids. 2. Experimental antitumor activities of N-substituted deacetylvinblastine amide (vindesine) sulfates
Journal of Medicinal Chemistry 1979.0
Synthesis and Biological Evaluation of a New Series of Highly Functionalized 7′-homo-Anhydrovinblastine Derivatives
Journal of Medicinal Chemistry 2013.0
Synthesis and Structure−Activity Relationship Studies of Cytotoxic Anhydrovinblastine Amide Derivatives
Journal of Natural Products 2009.0
Synthesis and structure–activity relationships study of novel anti-tumor carbamate anhydrovinblastine analogues
Bioorganic & Medicinal Chemistry 2007.0