| || Structure biological activity relationship of analogues of 2-Chlorobenzylidenemalononitrile : Riot control agent
Author : Gutch, P. K.;Kumar, Pravin;Suryanarayana, M. V. S.;Malhotra, R. C.
Source : Defence Science Journal ; Vol:55(4) ; 2005 ; pp 447-457
Subject : 623.459 Chemical Weapons
Keywords : Benzylidenemalonitriles;BMNs;Riot control agent;RD50;Hydrophobicity;High performance liquid chromatography;Diethylaminoethyl mercaptans;2-chlorobenzylidenemalononitrile;Sensory irritants
Abstract : The riot control agent 2-chlorobenzylidenemalononitrile (CS) and its ortho-and para-substituted benzylidenemalononitrile (BMN) analogues were synthesised and characterised by spectroscopic techniques (IR, NMR, and mass spectrometry) and microanalysis, and their structure biological activity relationship studies were carried out to know the factors responsible for sensory irritation. Hydrophobicity of substituted BMNs were determined by high performance liquid chromatography (HPLC), which is an important determinant of the irritancy. The vapour pressure of a compound is a physico-chemical property important for the assessment of its fate in the environment. The vapour pressures of BMNs were determined by static method by an isoteniscope. A systematic investigation of sensory irritation was carried out by evaluating decrease in respiratory rate (RD(subscript)50) in mice. The RD(subscript)50 as biological parameter was correlated with physical parameters such as hydrophobicity, vapour pressure, size of molecules, and chemical reactivity of its BMNs with dimethylaminoethyl mercaptans (DEAEMs) as a simulant of protein-SH group. A biosignificant correlation (0.75-0.80) was obtained by correlating all the above parameters using multiple linear regression equation.