Synthesis of acyclic analogs of Syringolin A as potential 20S proteasome inhibitors

doi:10.5246/jcps.2010.06.057

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Synthesis of acyclic analogs of Syringolin A as potential 20S proteasome
inhibitors

Yue Yuan, Xiao-Min Zou, Yan Niu, Feng-Rong Xu, Ke Mou, Bo Zhou, Chao Wang, Yong-Jian Li, Guan-Yu Yang, Ping Xu^*

Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2010-05-25 Revised:2010-10-15 Online:2010-11-30 Published:2010-11-30
Contact: Ping Xu*

Abstract

Abstract:

A series of acyclic analogs of natural product Syringolin A (SylA) were designed and synthesized during our synthetic efforts for SylA. These acyclic analogs were prepared through a seven-step linear strategy, with total yields varying from 20%-34% for one type of analogs and 12%-18% for the other. These compounds bear a common structure of peptidyl vinyl amide, which reacts irreversibly with the proteasomal active site Thr1O^γ through Michael-type 1,4-addition. Therefore, these acyclic analogs may function the same way as SylA, as potential 20S proteasome inhibitors.

Key words: Syringolin A, 20S proteasome, Peptidyl vinyl amide

CLC Number:

R916.4

Supporting:

Yue Yuan, Xiao-Min Zou, Yan Niu, Feng-Rong Xu, Ke Mou, Bo Zhou, Chao Wang, Yong-Jian Li, Guan-Yu Yang, Ping Xu^*. Synthesis of acyclic analogs of Syringolin A as potential 20S proteasome
inhibitors [J]. , DOI: 10.5246/jcps.2010.06.057.

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[2]	Yong-Jian Li, Feng-Rong Xu, Yan Niu, Xiao-Min Zou, Yue Yuan, Hai-Fei Gao, Chao Wang, Guan-Yu Yang, Qi Sun, Ping Xu^* . Design, synthesis and biological evaluation of pyrrolidinone analogs as potential 20S proteasome inhibitors [J]. , 2011, 20(6): 564-571.

Synthesis of acyclic analogs of Syringolin A as potential 20S proteasome
inhibitors

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