STEREOSTRUCTURE, ANTIMICROBIAL AND CYTOTOXIC ACTIVITY OF CYCLO-HEXENE, CYCLOHEXANOL AND PYRIDINE DERIVATIVES SYNTHESIZED FROM CHALCONES
AbstractThe 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.
Article Information
63
2084-2094
857KB
1628
English
IJPSR
Habiba Tahira Hussain , Mohammad Osama* and Wajid Hussain
Department of Chemistry, Aligarh Muslim University, Aligarh, Uttar Pradesh, India
osama.alig@gmail.com
20 November, 2013
20 February, 2014
09 March, 2014
http://dx.doi.org/10.13040/IJPSR.0975-8232.5(5).2084-94
01, May 2014