Insights into the structure–activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

Aashay K. Shah; Shan Qian; Dawei Zhang; Sarah A. Head; Jun O. Liu; Zhendong Jin

doi:10.1016/j.bmcl.2016.04.044

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Insights into the structure–activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

Journal article

Peer reviewed

Insights into the structure–activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

Aashay K. Shah, Shan Qian, Dawei Zhang, Sarah A. Head, Jun O. Liu and Zhendong Jin

Bioorganic & medicinal chemistry letters, Vol.26(12), pp.2890-2892

06/15/2016

DOI: 10.1016/j.bmcl.2016.04.044

PMID: 27133592

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Abstract

[Display omitted] Compound ZJ-101, a structurally simplified analog of the marine natural product superstolide A, was previously developed in our laboratory. In the subsequent structure–activity relationship study, a new analog ZJ-102 was designed and synthesized to probe the importance of the cyclohexenyl group through its replacement to a phenyl group using a concise and convergent synthetic approach. The biological evaluation showed that this new analog ZJ-102 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the cyclohexenyl ring (along with its two stereogenic centers) present in ZJ-101 is important for its anticancer activity.

Anticancer agent

Asymmetric synthesis

Drug design

Structure–activity relationship

Superstolide A analog

Details

Title: Subtitle: Insights into the structure–activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring
Creators: Aashay K. Shah - University of Iowa
Shan Qian - University of Iowa
Dawei Zhang - University of Iowa
Sarah A. Head - Johns Hopkins Medicine
Jun O. Liu - Johns Hopkins Medicine
Zhendong Jin - University of Iowa
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry letters, Vol.26(12), pp.2890-2892
Publisher: Elsevier Ltd
DOI: 10.1016/j.bmcl.2016.04.044
PMID: 27133592
ISSN: 0960-894X
eISSN: 1464-3405
Grant note: name: Office of the Vice President for Research and Economic Development; DOI: 10.13039/100008893, name: University of Iowa; name: InnoBioPharma, LLC, award: D2015070002; DOI: 10.13039/100012675, name: University of Iowa Center for Biocatalysis and Bioprocessing; DOI: 10.13039/100000002, name: NIH, award: 2T32GM008365
Language: English
Date published: 06/15/2016
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
Record Identifier: 9984366037302771

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