Synthesis of stereochemically diverse cyclic analogs of tubulysins

Park, Yunjeong; Bae, Song Yi; Hah, Jung-Mi; Lee, Sang Kook; Ryu, Jae-Sang

doi:10.1016/j.bmc.2015.10.003

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Synthesis of stereochemically diverse cyclic analogs of tubulysins

Park, Yunjeong;
Bae, Song Yi;
Hah, Jung-Mi;
Lee, Sang Kook;
Ryu, Jae-Sang

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WEB OF SCIENCE

17

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16

초록

The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization. (C) 2015 Elsevier Ltd. All rights reserved.

키워드

Tubulysin; Antitumor agents; Peptides; Asymmetric catalysis; Hetero Diels-Alder reaction; SIMPLIFIED PRETUBULYSIN DERIVATIVES; N-METHYLAMINO ACIDS; BIOLOGICAL EVALUATION; BOND FORMATION; RACEMIZATION; CYTOTOXICITY; MYXOBACTERIA; DANISHEFSKYS; ANTICANCER; INHIBITORS

제목: Synthesis of stereochemically diverse cyclic analogs of tubulysins

저자: Park, Yunjeong; Bae, Song Yi; Hah, Jung-Mi; Lee, Sang Kook; Ryu, Jae-Sang

DOI: 10.1016/j.bmc.2015.10.003

발행일: 2015-11

유형: Article

저널명: Bioorganic & Medicinal Chemistry

권: 23

호: 21

페이지: 6827 ~ 6843

언어: ENG

출판사: PERGAMON-ELSEVIER SCIENCE LTD

발행국가: 영국

분량: 17 페이지

ISSN: E 1464-3391
P 0968-0896