SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SOME NEW BAYLIS-HILLMAN DERIVED CINNAMYL SUBSTITUTED QUINAZOLINONE DERIVATIVESAbstract
A series of new Baylis–Hillman derived cinnamyl substituted quinazolinone derivatives have been synthesized by the condensation reaction between Baylis-Hillman bromides and quinazolinones in a simple and efficient manner in less reaction time with high yields. Methyl quinazolinone yields two isomers of Baylis-Hillman derived 3–N-cinnamyl substituted quinazoline-4-one derivatives and 4-O-cinnamyl substituted quinazoline derivatives, and the structures were confirmed by X-ray crystallography. All the newly synthesized compounds were characterized by their spectral data and evaluated their antibacterial and antifungal activity. The compounds (3a, 4a) without any substitution at the aryl group exhibited good antibacterial activity especially on S. epidermidis (gram positive), Replacement of hydrogen atom of the aryl group by CF3 (3c, 4c) or by fluorine (3g) exhibited significant antibacterial activity on both gram-positive (S. epidermidis) and gram-negative (K. pneumonia) organisms compared to other compounds. All the compounds exhibited interesting antifungal activity on C. albicans microorganism exclusively and inactive on the remaining organisms. Compound 3a and 4f exhibited good antifungal activity compared to the other compounds.
L. D.Chebrolu *, U. Kiranmayi, O. M. Jhansi, R. Vadla, S. Balasubramanian, J. R. Vidya and S. N. M. Upadhyayula
Crop Protection Chemicals Division, Indian Institute of Chemical Technology, Tarnaka, Hyderabad, India.
27 February 2014
15 April 2014
30 May 2014
01 September 2014