Total Synthesis of an Epothilone Analogue Based on the Amide-Triazole Bioisosterism

被引：0

作者：

Colombo, Eleonora ^{[1
]}

Coppini, Davide A. ^{[1
]}

Borsoi, Simone ^{[1
]}

Fasano, Valerio ^{[1
]}

Bucci, Raffaella ^{[2
]}

Bonato, Francesca ^{[1
]}

Bonandi, Elisa ^{[1
]}

Vasile, Francesca ^{[1
]}

Pieraccini, Stefano ^{[1
]}

Passarella, Daniele ^{[1
]}

机构：

[1] Univ Milan, Dept Chem, Via Golgi 19, I-20133 Milan, Italy

[2] Univ Milan, Dept Pharmaceut Sci, Via Venezian 21, I-20133 Milan, Italy

来源：

CHEMPLUSCHEM | 2024年 / 89卷 / 10期

基金：

欧盟地平线“2020”;

关键词：

Epothilone; Macrolide; Triazole; Tubulin; Ixabepilone; STEREOSELECTIVE-SYNTHESIS; MICROTUBULE ALTERATIONS; CONFORMATION; EQUIVALENT; TUBULIN; SAR;

D O I：

10.1002/cplu.202400413

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Epothilones are 16-membered macrolides that act as microtubule-targeting agents to tackle cancer. Many synthetic analogues have been investigated for their activity, yet often based on macrolide structures. A notable exception is Ixabepilone, an azalide whose metabolic stability and pharmacokinetics are significantly improved. Exploiting the amide-triazole bioisosterism, in this work we report the synthesis of the first generation of epothilones lacking the macrolide or azalide structure, with the ester or amide linkage replaced by a triazole unit. Together with the synthesis of this new analogue, computational and biological evaluations have been performed too. Epotriazole: Exploiting the amide-triazole bioisosterism, in this work we report the synthesis of the first generation of epothilones lacking the macrolide or azalide structure, with the ester or amide linkage replaced by a triazole unit. image

引用

页数：5

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