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1H, 13C and 15N NMR spectroscopic characterization of unexpected degradation products of the nifedipine analogue bis(2-cyanoethyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate

✍ Scribed by Edith Gössnitzer; Klaus Görlitzer; Hans J. Baltrusch

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
108 KB
Volume
40
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

In the course of saponification experiments with bis(2‐cyanoethyl) 2,6‐dimethyl‐4‐(2‐nitrophenyl)‐1,4‐dihydro‐3,5‐pyridinedicarboxylate (1), an analogue of the calcium channel blocker nifedipine, three unexpected degradation products were isolated. The compounds were identified as 3‐(2‐acetamido‐1‐carboxy‐1‐propenyl)‐1‐hydroxy‐2‐indolecarboxylic acid (3), 9‐hydroxy‐1,3‐dimethyl‐β‐carboline‐4‐carboxylic acid (4) and 6‐hydroxy‐2,4‐dimethyl‐5‐oxo‐5,6‐dihydrobenzo[c][2,7]naphthyridine‐1‐carboxylic acid (6). The structures of these compounds were deduced from one‐ and two‐dimensional ^1^H, ^13^C and natural abundance ^15^N NMR experiments (^1^H,^1^H‐COSY, gs‐HSQC, gs‐HMBC, ^15^N gs‐HMBC), and corroborated by comparison of their NMR data with the respective data for structurally similar compounds. Copyright © 2002 John Wiley & Sons, Ltd.

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