PMID: 3747723Sep 22, 1986Paper

Conjugated and cross-conjugated mesomeric betaines. Correlation of electroreduction with structure and physiological activity

Life Sciences
J R AmesP Kovacic

Abstract

Electroreduction studies were performed on several cross-conjugated mesomeric betaines containing the fused pyrazolium (2) and fused imidazolium (3) ring systems. Studies at acidic pH were of principal interest. Substituent effects for 2 were in line with prior findings, and reduction potentials were comparatively negative (-0.96 to -1.34 V). Reduction potentials fit the modified Hammett equation. Compound 3 was more readily reduced (-0.88 V). The related psi-oxatriazoles (6) gave values in the range of -0.85 to -1.22 V. The electrochemical characteristics are compared with those of the mesoionic sydnones (4) and sydnoneimines (5). These mesoionic compounds were generally reduced at more positive potentials than 2 and 3. A relationship between electroreduction and physiological activity is proposed. The overall results are in keeping with the hypothesis of widespread participation of iminium-type species in biological systems.

References

Jan 1, 1978·Journal of Medicinal Chemistry·E M HodnettJ Amirmoazzami
Dec 17, 1985·Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences·S Orrenius
Jan 1, 1985·Advances in Enzyme Regulation·E Cadenas, H Sies
Apr 1, 1985·Journal of Pharmaceutical Sciences·M D RyanP Kovacic
Feb 1, 1967·Journal of Pharmaceutical Sciences·L B Kier, E B Roche

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