DICHOTOMOUS NITRIC OXIDE RELEASE PROFILES OF TWO ISOMERIC FAMILIES OF N-NITROSATED SECONDARY AMINES

Dillip K. Mohanty, Alec Badour, Yawing Ji, Sarah Huff, Anton Jensen, David E. Ash

Department of Chemistry and Biochemistry, Central Michigan University, Mount Pleasant, USA

Abstract

Nitric oxide (NO) is known to inhibit excessive proliferation of vascular smooth muscle cells, which contributes to the progression of atherosclerosis. We have prepared two isomeric families of secondary amines, which can donate NO in a slow and sustained manner after being nitrosated. These secondary amines were prepared by the reactions of 2,6-difluoro-3-nitrobenzonitrile (2,6-DFNBN) (O family) or 2,4-difluoro-5-nitrobenzonitrile (2,4-DFNBN) (P family) and two equivalents of homologous aliphatic primary amines. The NO release rate of the O family of compounds decrease with increasing aliphatic chain lengths whereas the opposite is true for the P family of compounds. We will discuss possible reason for this opposing trend.

Keywords: Nitric oxide, slow and sustained release, atherosclerosis.