Document Detail

Synthesis and calcium channel antagonist activities of 3-nitrooxyalkyl, 5-alkyl 1,4-dihydro-2,6-dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-3, 5-pyridinedicarboxylates.
MedLine Citation:
PMID:  11902654     Owner:  NLM     Status:  MEDLINE    
A group of racemic 3-[(2-nitrooxyethyl), (3-nitrooxypropyl), (4-nitrooxybutyl) or (1,3-dinitrooxy-2-propyl)], 5-methyl (ethyl or propyl) 1,4-dihydro-2,6-dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-3,5-pyridinedicarboxylates (18-29) were synthesized using modified Hantzsch reaction that involved the condensation of 2-nitrooxyethyl (8), 3-nitrooxypropyl (9), 4-nitrooxybutyl (10) or 1,3-dinitrooxy-2-propyl (13) acetoacetate with methyl (14), ethyl (15) or isopropyl (16) 3-aminocrotonate and 1-methyl-5-nitroimidazole-2-carboxaldehyde (17). In vitro calcium channel antagonist activities were determined using a guinea pig ileum longitudinal smooth muscle assay. Compounds 18-29 exhibited superior, or equipotent, calcium antagonist activity (IC50= 10(11) - 10(-13) M range) relative to the reference drug nifedipine (IC50 = 1.07 +/- 0.12 x 10(-11) M), which could serve as potential probes to investigate the in vivo release of nitric oxide which induces vascular muscle relaxation.
Ramin Miri; H Niknahad; Gh Vesal; A Shafiee
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Farmaco (Società chimica italiana : 1989)     Volume:  57     ISSN:  0014-827X     ISO Abbreviation:  Farmaco     Publication Date:  2002 Feb 
Date Detail:
Created Date:  2002-03-20     Completed Date:  2002-09-23     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8912641     Medline TA:  Farmaco     Country:  Italy    
Other Details:
Languages:  eng     Pagination:  123-8     Citation Subset:  IM    
Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Science, Iran.
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MeSH Terms
Calcium Channel Blockers / chemical synthesis*,  pharmacology*
Calcium Channels / metabolism*
Guinea Pigs
Ileum / drug effects
Inhibitory Concentration 50
Molecular Structure
Muscle Contraction / drug effects
Muscle, Smooth / drug effects
Organ Culture Techniques
Pyridines / chemical synthesis*,  pharmacology*
Structure-Activity Relationship
Reg. No./Substance:
0/Calcium Channel Blockers; 0/Calcium Channels; 0/Pyridines

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