STEREOSTRUCTURE, ANTIMICROBIAL AND CYTOTOXIC ACTIVITY OF CYCLO-HEXENE, CYCLOHEXANOL AND PYRIDINE DERIVATIVES SYNTHESIZED FROM CHALCONES

The main objective of this work is to study the stereostructures and biological activity of some highly substituted cyclohexenes, cyclohexanols and the intermediates there in. In order to get the desired cyclohexenes, the  synthesis of cyclohexanols  2,4-bis(4-chlorobenzoyl)-1-(4-chlorophenyl)-3,5-bis(4-methoxyphenyl)-and 2,4-bis(4-chlorobenzoyl)-1,3,5-tris(4-chlorophenyl)-cyclohexan-1-ols (1b and 2b) from 4’- chloro-4-methoxy- and 4,4’- dichlorochalcones(1 and 2) via 1,5-bis(4-chlorophenyl)-3-(4-methoxyphenyl)- and 1,3,5-tris(4-chlorophenyl)-pentan-1,5-diones(1a and 2a ) using p-chloroacetophenone in the presence of sodium hydroxide(molar ratio, 2:1:10) is first described. These are then  dehydrated with p-TsOH which afford typical cyclohexenes, 4,6-bis(4-chlorobenzoyl) -1- (4-chlorophenyl) – 3,5 –bis (4-methoxyphenyl) and 4,6 –bis(4-chlorobenzoyl)-1,3,5 –tris (4-chlorophenyl) –cyclohex-1-enes (1c) and (2c) in quantitative  yields containing  β,γ-unconjugated double bond following stereoselective syn elimination. Also, in an attempt to synthesize dithiazolidin-4-one (3), the reaction of 1, 5-dione (1a) with mercapto acetic acid and ammonium carbonate is adopted. However, it fails to produce (3) and only a pyridine derivative, 2, 6-bis (4-chlorophenyl)-4-(4-methoxyphenyl) pyridine (4) is obtained.in 87% yield. Structural assignment, stereochemistry and biological assays are discussed. The characterization is done by modern spectroscopic techniques.