Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives

The structure–activity relationship study on 6-unsubstituted-1,4-dihydropyridine derivatives and 2,6-dihydro-1,4-dihydropyridine derivatives are reported as selective N-type calcium channel blockers over L-type calcium channel. A structure–activity relationship study of 6-unsubstituted-1,4-dihydropy...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-06, Vol.22 (11), p.3639-3642
Main Authors: Yamamoto, Takashi, Niwa, Seiji, Tokumasu, Munetaka, Onishi, Tomoyuki, Ohno, Seiji, Hagihara, Masako, Koganei, Hajime, Fujita, Shin-ichi, Takeda, Tomoko, Saitou, Yuki, Iwayama, Satoshi, Takahara, Akira, Iwata, Seinosuke, Shoji, Masataka
Format: Article
Language:English
Subjects:
1,4-Dihydropyridine derivative
Administration, Oral
Analgesics
Analgesics - chemical synthesis
Analgesics - chemistry
Analgesics - pharmacology
Animals
Biological and medical sciences
calcium channel blockers
Calcium Channel Blockers - chemical synthesis
Calcium Channel Blockers - chemistry
Calcium Channel Blockers - pharmacology
calcium channels
Calcium Channels, N-Type - chemistry
Calcium Channels, N-Type - metabolism
Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Carboxylic Acids - pharmacology
Dihydropyridines - chemistry
Drug Evaluation, Preclinical
Formaldehyde - toxicity
Medical sciences
N-Type calcium channel blocker
Pain Measurement - drug effects
Pharmacology. Drug treatments
Rats
Structure-Activity Relationship
Structure–activity relationships
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Summary:The structure–activity relationship study on 6-unsubstituted-1,4-dihydropyridine derivatives and 2,6-dihydro-1,4-dihydropyridine derivatives are reported as selective N-type calcium channel blockers over L-type calcium channel. A structure–activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.04.051