Document Detail


Synthesis and structure-activity relationship studies of 3-biaryl-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters.
MedLine Citation:
PMID:  22398259     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Stille cross coupling protocols were utilized for the synthesis of 3-(biaryl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl esters, which furnished products in high yields where in some cases Suzuki coupling under the conditions utilized provided complex reaction mixture. Samarium iodide reduction of the resulting coupling products produced both of the 2β-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers and the 2α-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers. Among the series synthesized, the benzothiophene substituted compounds demonstrated significant binding profiles of inhibition of WIN 35,438 with 177-fold selectivity for DAT versus SERT.
Authors:
Lokman Torun; Bertha K Madras; Peter C Meltzer
Related Documents :
14682699 - Enantioselective lewis acid-catalyzed mukaiyama-michael reactions of acyclic enones. ca...
15387549 - Synthesis of new monodentate spiro phosphoramidite ligand and its application in rh-cat...
20450219 - Desymmetrization of meso-1,2-diols via the dynamic kinetic resolution of its monodichlo...
12945779 - Formation of optically active chromanes by catalytic asymmetric tandem oxa-michael addi...
16897829 - Optically active trans-2-aminocyclopentanols: chemoenzymatic preparation and applicatio...
15548079 - Convenient catalytic, enantioselective conjugate reduction of nitroalkenes using cuf2.
21566139 - Crystal structure of leishmania major peroxidase and characterization of the compound i...
19692149 - Captopril and 6-mercaptopurine: whose sh possesses higher antioxidant ability?
7954109 - Degradation of morpholine by mycobacterium aurum mo1.
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-02-08
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  20     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2012 Apr 
Date Detail:
Created Date:  2012-04-06     Completed Date:  2012-09-04     Revised Date:  2013-06-26    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  2762-72     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 Elsevier Ltd. All rights reserved.
Affiliation:
TUBITAK MAM Chemistry Institute P K 21 Gebze, Kocaeli 41470, Turkey. lokman.torun@mam.gov.tr
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Bicyclo Compounds / chemistry*
Carboxylic Acids / chemistry*
Cocaine / analogs & derivatives,  pharmacology
Dopamine Plasma Membrane Transport Proteins / antagonists & inhibitors,  metabolism
Dopamine Uptake Inhibitors / chemical synthesis*,  chemistry,  pharmacology*
Esters / chemical synthesis,  chemistry,  pharmacology*
Humans
Molecular Structure
Serotonin Plasma Membrane Transport Proteins / metabolism
Serotonin Uptake Inhibitors / chemical synthesis*,  chemistry,  pharmacology*
Structure-Activity Relationship
Grant Support
ID/Acronym/Agency:
DA 06303/DA/NIDA NIH HHS; DA 11542/DA/NIDA NIH HHS; DA 7-8825/DA/NIDA NIH HHS; R01 DA011542-10/DA/NIDA NIH HHS
Chemical
Reg. No./Substance:
0/Bicyclo Compounds; 0/Carboxylic Acids; 0/Dopamine Plasma Membrane Transport Proteins; 0/Dopamine Uptake Inhibitors; 0/Esters; 0/Serotonin Plasma Membrane Transport Proteins; 0/Serotonin Uptake Inhibitors; 50-36-2/Cocaine; 50370-56-4/(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
Comments/Corrections

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


Previous Document:  Synthesis and evaluation of disulfide bond mimetics of amylin-(1-8) as agents to treat osteoporosis.
Next Document:  Atypical presentation of cauda equina syndrome secondary to lumbar disc herniation.