Document Detail


Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.
MedLine Citation:
PMID:  12515475     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
An efficient one-pot synthesis is described of 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole (CTr), a potent estrogen agonist from food plants. For the procedure, gramine is treated with dimethyl sulfate and sodium in ethanol at room temperature. Quenching of the reaction with water and workup of the product provides CTr in approximately 75% yield.
Authors:
Richard E Staub; Leonard F Bjeldanes
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  68     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2003 Jan 
Date Detail:
Created Date:  2003-01-07     Completed Date:  2003-06-20     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  167-9     Citation Subset:  IM    
Affiliation:
Department of Nutritional Sciences and Toxicology, University of California, Berkeley, California 94720-3104, USA.
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MeSH Terms
Descriptor/Qualifier:
Brassica / chemistry
Catalysis
Estrogens, Non-Steroidal / analysis,  chemical synthesis*
Indoles / analysis,  chemical synthesis*,  pharmacology
Isoflavones*
Magnetic Resonance Spectroscopy
Molecular Structure
Phytoestrogens
Plant Preparations
Receptors, Estrogen / agonists*
Structure-Activity Relationship
Temperature
Water
Grant Support
ID/Acronym/Agency:
5-T32ES07075/ES/NIEHS NIH HHS; CA69056/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Estrogens, Non-Steroidal; 0/Indoles; 0/Isoflavones; 0/Phytoestrogens; 0/Plant Preparations; 0/Receptors, Estrogen; 64299-06-5/5,6,11,12,17,18-hexahydrocyclononatriindole; 700-06-1/indole-3-carbinol; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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