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
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...
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| Published in: | Farmaco (Società chimica italiana : 1989) Vol. 57; no. 2; pp. 123 - 128 |
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| Language: | English |
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01-02-2002
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| Abstract | 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 (IC
50=10
−11–10
−13 M range) relative to the reference drug nifedipine (IC
50=1.07±0.12×10
−11 M), which could serve as potential probes to investigate the in vivo release of nitric oxide which induces vascular muscle relaxation. |
|---|---|
| AbstractList | 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. 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 (IC 50=10 −11–10 −13 M range) relative to the reference drug nifedipine (IC 50=1.07±0.12×10 −11 M), which could serve as potential probes to investigate the in vivo release of nitric oxide which induces vascular muscle relaxation. |
| Author | Miri, Ramin Vesal, Gh Shafiee, A Niknahad, H |
| Author_xml | – sequence: 1 givenname: Ramin surname: Miri fullname: Miri, Ramin email: mirir@sums.ac.ir organization: Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Science, P.O. Box 71345-1149, Shiraz, Iran – sequence: 2 givenname: H surname: Niknahad fullname: Niknahad, H organization: Department of Pharmacology, Faculty of Pharmacy, Shiraz University of Medical Science, Shiraz, Iran – sequence: 3 givenname: Gh surname: Vesal fullname: Vesal, Gh organization: Department of Pharmacology, Faculty of Pharmacy, Shiraz University of Medical Science, Shiraz, Iran – sequence: 4 givenname: A surname: Shafiee fullname: Shafiee, A organization: Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Science, Tehran, Iran |
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| Cites_doi | 10.1139/y90-224 10.1016/0928-0987(95)00029-1 10.1016/S0014-2999(99)00237-X 10.1016/S0165-6147(98)01265-6 10.1002/ardp.19963290105 10.1248/cpb.27.1426 10.1021/jo01125a018 10.1002/ddr.3 10.1021/jm981114c 10.1002/jps.2600830809 10.1002/ardp.19973300905 10.1248/cpb.41.108 10.1139/y79-124 10.2165/00003495-199855040-00003 10.1097/00005344-198800125-00020 10.1002/jhet.5570290461 10.1038/sj.bjp.0702162 10.1161/01.CIR.92.5.1079 10.1021/cr00072a001 |
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| Keywords | Calcium channels Dihydropyridine Nitrooxyalkyl Nitroimidazole Organic nitrate |
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| SubjectTerms | Animals Calcium Channel Blockers - chemical synthesis Calcium Channel Blockers - pharmacology Calcium channels Calcium Channels - metabolism Dihydropyridine Guinea Pigs Ileum - drug effects Inhibitory Concentration 50 Male Molecular Structure Muscle Contraction - drug effects Muscle, Smooth - drug effects Nitroimidazole Nitrooxyalkyl Organ Culture Techniques Organic nitrate Pyridines - chemical synthesis Pyridines - pharmacology Structure-Activity Relationship |
| Title | 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 |
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