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PMID: 19434636 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Stereodivergent synthesis of 17-alpha and 17-beta-alpharyl steroids: application and biological evaluation of D-ring cortistatin analogues.

Angewandte Chemie (International ed. in English) ·Vol. 48 ·No. 24 ·2009-00-00 ·Pages 4328-31

Shi J, Shigehisa H, Guerrero CA, Shenvi RA, Li CC, Baran PS

Abstract

One stereocenter makes all the difference: The synthesis and biological evaluation of 17-epi-cortistatin A is reported from a common intermediate used to procure natural cortistatin A. The synthesis features a unique stereocontrolled Raney-Ni reduction process that can be employed to reliably produce both alpha- and beta-configured D-ring aryl steroids. Biological evaluations of these "cortalogs" are reported for the first time.

MeSH Terms
Angiogenesis Inhibitors/chemical synthesis,chemistry,pharmacology Cell Line Humans Isoquinolines/chemical synthesis,chemistry,pharmacology Polycyclic Compounds/chemical synthesis,chemistry,pharmacology Stereoisomerism Steroids/chemical synthesis,chemistry,pharmacology Structure-Activity Relationship
Chemicals
Angiogenesis Inhibitors Isoquinolines Polycyclic Compounds Steroids cortistatin A
Authors & Affiliations
6 authors, click to expand affiliations / ORCID
Shi Jun
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA.
Shigehisa Hiroki
Guerrero Carlos A
Shenvi Ryan A
Li Chuang-Chuang
Baran Phil S
References (15)
15 references, click to expand
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Article Info
Journal
Angewandte Chemie (International ed. in English)
Abbr.
Angew Chem Int Ed Engl
ISSN
1521-3773
DOI
10.1002/anie.200901116
Published
2009-00-00
Pages
4328-31
Language
English
Region
Germany
NLM ID
0370543
PMCID
PMC3495592
Subset
IM
Grants
NIGMS NIH HHS · R01 GM073949 · United States
External Links
PubMed source DOI: 10.1002/anie.200901116 PMC Full Text View journal details
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