Design and syntheses of 4-[3-(1-methoxycarbonyl-1,6-dihydropyridyl)]- and 4-[3-(1-methoxycarbonyl-4-substituted-1,4-dihydropyridyl)]- derivatives of alkyl 1,4-dihydro-2,6-dimethyl-3-nitro-5-pyridine-carboxylates with calcium channel modulating activities

Mohsen Amini; Carol-Anne McEwen; Edward E. Knaus

doi:10.3998/ark.5550190.0002.604

PDF
Print
Share+
- Twitter
- Facebook
- Reddit
- Mendeley

Design and syntheses of 4-[3-(1-methoxycarbonyl-1,6-dihydropyridyl)]- and 4-[3-(1-methoxycarbonyl-4-substituted-1,4-dihydropyridyl)]- derivatives of alkyl 1,4-dihydro-2,6-dimethyl-3-nitro-5-pyridine-carboxylates with calcium channel modulating activities

Mohsen Amini; Carol-Anne McEwen; Edward E. Knaus

Volume 2001, Issue 6, Commemorative Issue in Honor of Prof. Rudolph A. Abramovitch on the occasion of his 70th anniversary, pp. 42-62

DOI: http://dx.doi.org/10.3998/ark.5550190.0002.604

Paper ID: RA-212RP

Received on 2001-04-06; Accepted on 2001-09-18; Published on 2001-09-26

Permissions: This work is licensed under a Creative Commons Attribution-NonCommercial 3.0 License. Please contact [email protected] to use this work in a way not covered by the license.

For more information, read Michigan Publishing's access and usage policy.

- 150% +

image text pdf

« Prev Next »

Issue in Honor of Prof. Rudolph Abramovitch ARKIVOC 2001 (vi) 42-62 Isobutyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-[3-(1-methoxycarbonyl-4-methyl-1,4-dihydropyridyl)]-5pyridinecarboxylate (17a). Yield: 6%; IR (KBr): 3300 (NH), 1710 (NCO2Me), 1685 (CO2Bu-i), 1510, 1310 (NO2) cm-1; 1H NMR (Me2SO-d6, 25 °C), mixture of two rotamers and/or diastereomers (ratio of 3.3:1) as determined from the integrals for the NCO2Me resonances: d 0.85-1.20 [m, 9H, C-4’ CH3, CH(CH3)2], 1.91-1.98 [m, 1H, CH2CH(CH3)2], 2.22 and 2.27 (two s, 3H total, C-6 CH3), 2.41 and 2.43 (two s, 3H total, C-2 CH3), 2.78 2.89 (m, 1H, H-4’), 3.69 and 3.71 (two s, 3H total, NCO2CH3), 3.80-3.87 [m, 2H, CH2CH(CH3)2], 4.885.05 (m, 2H, H-4, H-5’), 6.36-6.53 (m, 1H, H-6’), 6.62 (br s, 1H, H-2’), 9.51 and 9.62 (two br s, 1H total, NH). Anal. calcd. for C20H27N3O6: C 59.25, H 6.71, N 10.36. Found: C 58.93, H 6.39, N 10.41. Issue in Honor of Prof. Rudolph Abramovitch ARKIVOC 2001 (vi) 42-62 t-Butyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-[3-(1-methoxycarbonyl-4-methyl-1,4-dihydropyridyl)]-5pyridinecarboxylate (18a). Yield: 6%; IR (KBr): 3300 (NH), 1710 (NCO2Me), 1690 (CO2Bu-t), 1510, 1310 (NO2) cm-1; 1H NMR (Me2SO-d6, 25 °C), mixture of two rotamers and/or diastereomers (ratio of 1.8:1) as determined from the integrals for the NCO2Me resonances: d 0.90-1.04 (m, 3H, C-4’ CH3), 1.35 (s, 9H, C(CH3)3], 2.30 and 2.39 (two s, 3H total, C-6 CH3), 2.41 and 2.45 (two s, 3H total, C-2 CH3), 2.78-2.92 (m, 1H, H-4’), 3.69 and 3.70 (two s, 3H total, NCO2CH3), 4.86-5.01 (m, 2H, H-4, H-5’), 6.34-6.52 (m, 1H, H-6’), 6.58 (br s, 1H, H-2’), 9.50 and 9.60 (two br s, 1H total, NH). Anal. calcd. for C20H27N3O6: C 59.25, H 6.71, N 10.36. Found: C 58.61, H 6.02, N 9.91. Methyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-[3-(1-methoxycarbonyl-4-n-butyl-1,4-dihydropyridyl)]-5pyridinecarboxylate (14b). Yield: 6%; IR (KBr): 3300 (NH), 1710 (NCO2Me), 1690 (CO2Me), 1507, 1310 (NO2) cm-1; 1H NMR (Me2SO-d6, 25 °C), mixture of two rotamers and/or diastereomers (ratio of 1.2:1) as determined from the integrals for the NCO2Me resonances: d 0.78-0.88 (m, 3H, CH2CH2CH2CH3), 1.10-1.70 (m, 6H, CH2CH2CH2CH3), 2.17 and 2.26 (two s, 3H total, C-6 CH3), 2.30 and 2.49 (two s, 3H total, C-2 CH3), 2.84 2.98 (m, 1H, H-4’), 3.71 (s, 3H, CO2CH3), 3.80 and 3.83 (two s, 3H total, NCO2CH3), 4.90-4.98 (m, 2H, H4, H-5’), 6.43-6.61 (m, 1H, H-6’), 6.70 (br s, 1H, H-2’), 9.48 and 9.67 (two br s, 1H total, NH). Anal. calcd. for C20H27N3O6: C 59.25, H 6.71, N 10.36. Found: C 58.96, H 6.94, N 10.02. ISSN 1424-6376 Page 56 ©ARKAT USA, Inc

« Prev Next »