SYNTHESIS AND PRELIMINARY ALKYLATING ACTIVITIES OF CERTAIN NEW 1,4-DIHYDROPYRIDINES, PYRIDINIUM SALTS AND 2,7-DIAZABICYCLO [4.1.0] HEPT-3-ENES

Document Type : Original Article

Authors

Department of Pharmaceutical Medicinal Chemistry, Faculty of Pharmacy, Assiut University, Assiut, Egypt

Abstract

3-Substituted-1-{2-chloro- or [2-bis (2-chloroethyl)amino]}ethyl-1,4-dihydropyridines 3 and 6 were prepared by reduction of the corresponding pyridinium chlorides 2 and 5 with sodium dithionite in alkaline medium. The l,3-dipolar cycloaddition of either phenylsulphonyl or p-tolylsulphonyl azides to the l,4-dihydropyridines 3 afforded the corresponding 2,7-diazabicyclo[4.1. 0]hept-3-enes 7. The alkylating activities of twelve new compounds (2b-d; 3b,c;  5a-c and 7a-d) were determined kinetically in comparison to chlorambucil as a reference drug. Compounds 5a-c showed higher activities than chlorambucil while 2c,d and 7a,b showed lower activities. The dihydropyridines (the CDS) 3b,c were inactive as alkylating agents as expected.