On the relationship between the substitution pattern of thiobenzanilides and their antimycobacterial activity.
The goal of this work was to shed more light on a preliminary finding about the relationship between the substitution in the thioacyl part of thiobenzanilides and their antituberculous effect. Thus, we prepared a set of 14 derivatives, out of which eight had not yet been reported, and the compounds were evaluated for antimycobacterial activity on a panel of four Mycobacteria species, including Mycobacterium tuberculosis CNCTC My 331/88, Mycobacterium kansasii CNCTC My 235/80, Mycobacterium avium CNCTC My 330/88 and M. kansasii 6509/96. While the contribution of the substituents with differing electronic and lipophilicity characteristics in position 3 to the antituberculous activity was negligible, we found that unsubstituted position 4 in the thioacyl part appears to be a prerequisite for a thiobenzanilide derivative to possess appreciable biological activity.
Kunes
Jirí
J
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic. kunes@faf.cuni.cz
Balsánek
Vojtech
V
Pour
Milan
M
Waisser
Karel
K
Kaustová
Jarmila
J
D000813:Anilides / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D057927:Hydrophobic and Hydrophilic Interactions; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects; D009162:Mycobacterium avium; D019909:Mycobacterium kansasii; D009169:Mycobacterium tuberculosis; D013329:Structure-Activity Relationship
D000813:Anilides; D000900:Anti-Bacterial Agents; C034595:benzanilide