Synthesis and study of new paramagnetic and diamagnetic verapamil derivatives

Bognár, Balázs and Ahmed, Sahman and Kuppusamy, Laksmi and Selvendiran, Karuppaiyah and Khan, Mahmood and Jekö, József and Hankovszky, Olga and Kálai, Tamás and Kuppusamy, Periannan and Hideg, Kálmán (2010) Synthesis and study of new paramagnetic and diamagnetic verapamil derivatives. BIOORGANIC & MEDICINAL CHEMISTRY, 18 (8). pp. 2954-2963. ISSN 0968-0896

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Abstract

New derivatives of verapamil (1) modified with nitroxides and their precursors were synthesized and screened for reactive oxygen species (ROS)-scavenging activities. The basic structure was modified by changing the nitrile group to an amide or the methyl substituent on tertiary nitrogen with nitroxides and their reduced forms (hydroxylamine and secondary amines). Among the new verapamil derivatives compound 16B [Mohan, I. K.; Kahn, M.; Wisel, S.; Selvendiran, K.; Sridhar, A.; Carnes, C.A.; Bognár, B.; Kálai, T.; Hideg, K.; Kuppusamy, P. Am. J. Physiol. Heart Circ. Physiol. 2009, 296, 140], modified with hydroxylamine salt of 2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridine-1-yloxyl proved to be the best ROS scavenger in vitro and protected HSMC and CHO cells against H2O2 induced damage

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