Document Detail

Synthesis, structure and quantitative structure-activity relationships of sigma receptor ligands, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl) piperazines.
MedLine Citation:
PMID:  9313869     Owner:  NLM     Status:  MEDLINE    
A set of the title compounds having different substituents (R1, R2) on their phenyl groups was synthesized to find sigma receptor binding affinity. Among the compounds, 2b (R1 = R2 = Cl) has the most potent sigma 1-binding activity, while 2a (R1 = R2 = H, SA4503) was most selective to sigma 1 over sigma 2 receptor. The crystal structures of 2a and 2b were shown, by X-ray crystallography, to be similar except for the one torsional angle of their propylene parts. Quantitative structure-activity relationship study suggested the affinity of the compounds to the sigma 1 receptor was dependent on the electronic feature, Swain-Lupton's R or Sz that was derived by molecular orbital method, of R1 and R2.
K Fujimura; J Matsumoto; M Niwa; T Kobayashi; Y Kawashima; Y In; T Ishida
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  5     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  1997 Aug 
Date Detail:
Created Date:  1997-12-08     Completed Date:  1997-12-08     Revised Date:  2000-12-18    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  1675-83     Citation Subset:  IM    
Developmental Research Division, Santen Pharmaceutical Co., Ltd., Osaka, Japan.
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MeSH Terms
Analgesics, Opioid / chemistry,  metabolism
Anticonvulsants / chemistry,  metabolism
Crystallography, X-Ray
Guanidines / chemistry,  metabolism
Molecular Weight
Pentazocine / chemistry,  metabolism
Piperazines / chemical synthesis,  metabolism*
Receptors, sigma / metabolism*
Structure-Activity Relationship
Reg. No./Substance:
0/Analgesics, Opioid; 0/Anticonvulsants; 0/Guanidines; 0/Ligands; 0/Piperazines; 0/Receptors, sigma; 359-83-1/Pentazocine; 97-39-2/1,3-ditolylguanidine

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