Analogues of parthenin and their antibacterial activity

C. Ramesh; K. Harakishore; U.S.N. Murty; Biswanath Das

doi:10.3998/ark.5550190.0004.915

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Analogues of parthenin and their antibacterial activity

C. Ramesh; K. Harakishore; U.S.N. Murty; Biswanath Das

Volume 2003, Issue 9, Commemorative Issue in Honor of Prof. Asima Chatterjee on the occasion of her 85th anniversary, pp. 126-132

DOI: http://dx.doi.org/10.3998/ark.5550190.0004.915

Paper ID: AC-953KP

Received on 2003-10-01; Accepted on 2004-03-06; Published on 2004-03-12

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Analogues of Parthenin and their antibacterial activity1 C. Ramesh, K. Harakishore, U.S.N. Murty, and Biswanath Das* Organic Chemistry Division-I, Indian Institute of Chemical Technology, Uppal Road Hyderabad 500 007, India E-mail: [email protected] Dedicated to Professor Asima Chatterjee on her 85th birthday (received 01 Oct 03; accepted 06 March 04; published on the web 12 March 04) Abstract Regio- and stereoselective chemical modifications of parthenin, a naturally occurring pseudoguaianolide, afforded its various natural and unnatural analogues whose antibacterial activity was studied. Parthenin itself and some of the analogues showed significant activity and with only one exception all of the active compounds were found to contain an intact a- methylene-.-butyrolactone moiety. Keywords: Parthenin, pseudoguaianolide, analogues, antibacterial activity, a-methylene-.- butyrolactone Introduction Parthenin (1)2 is a major constituent of the aggressive and obnoxious herb, Parthenium hysterophorus L (Compositae). The compound is a sesquiterpenoid having a pseudoguaianolide structure. It contains an a-methylene-.-butyrolactone moiety (rind C) along with other functionalities and five chiral centers. The compound is interesting for its structural pattern2 as well as for its bioactivity including antimalarial,3 antiamoebic,4 and allelopathic properties.5 Here we report the preparation of different analogues of the compound and our studies on their antibacterial activity.