Collect. Czech. Chem. Commun. 1997, 62, 510-515
https://doi.org/10.1135/cccc19970510

A New Pharmacophore of Potential Antimycobacterial Activity: The Disulfide Group in the Ring of Alicyclic Compounds

Hans-Dietrich Stachela, Želmíra Odlerováb and Karel Waisserc

a Institute of Pharmacy and Food Chemistry, University of Munich, 80333 Munich, Germany
b Institute of Preventive and Clinical Medicine, 83 301 Bratislava, Slovak Republic
c Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic

Abstract

A series of thirty 2,3-dithiabicyclo[3.3.0]octa-4,8-diene derivatives was examined for antimycobacterial activity against Mycobacterium tuberculosis, M. kansasii, M. avium, and M. fortuitum. The structure-activity relationships were analysed by Free-Wilson method. The authors consider the disulfide moiety to be the pharmacophore of antimycobacterial activity. To verify the idea, several other monocyclic sulfides, 3,4-dihydro-1,2-dithiolane derivatives, were also evaluated.

Keywords: 2,3-Dithiabicyclo[3.3.0]octa-4,8-dienes; Antimycobacterial activity; Structure–activity relationships; Free-Wilson analysis.