Abstract:
:New analogues of nifedipine, in which the 2-nitrophenyl group at position 4 is replaced by a 1-methyl-5-nitro-2-imidazolyl substituent, were synthesized. The symmetrical dialkyl 1, 4-dihydro-2, 6-dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-3, 5-pyridinedicarboxylates were prepared by a classical Hantzsch condensation. The asymmetrical analogues were synthesized using a procedure reported by Iwanami that involved the condensation of alkylacetoacetate with methyl-, ethyl- or isopropyl3-aminocrotonate and 1-methyl-5-nitroimidazole-2-carboxaldehyde. Calcium channel antagonist activities were determined in vitro using a guinea pig ileum longitudinal smooth muscle (GPILSM)assay. Many compounds exhibited superior, or equipotent, calcium antagonist activity (IC(50) = 10(-10) to 10(-13) M range) relative to the reference drug nifedipine (IC(50) = 1.09 +/- 0.12 x 10(-11) M). Antinociceptive effects of some compounds were evaluated by the mouse tail-flick assay in vivo. Results demonstrate that some of the compounds were active as an antinociceptive.
journal_name
Arch Pharm (Weinheim)journal_title
Archiv der Pharmazieauthors
Miri R,Javidnia K,Kebriaie-Zadeh A,Niknahad H,Shaygani N,Semnanian S,Shafiee Adoi
10.1002/ardp.200300762keywords:
subject
Has Abstractpub_date
2003-09-01 00:00:00pages
422-8issue
9eissn
0365-6233issn
1521-4184journal_volume
336pub_type
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