Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives.
New 1-adamanyl-1,3,4-thiadiazole derivatives namely, 5-(1-adamantyl)-1,3,4-thiadiazoline-2-thione 3, 5-(1-adamantyl)-3-(benzyl- or 4-substituted benzyl)-1,3,4-thiadiazoline-2-thione 4a-d, 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-thiadiazoline-2-thiones 5a-c, 2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]acetic acid 7, (±)-2-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid 9, 3-[5-(1-adamantyl)-2-thioxo-1,3,4-thiadiazolin-3-yl]propionic acid 11, N-[5-(1-adamantyl)-1,3,4-thiadiazol-2-yl]-N'-arylthioureas 15a-c and 5-(1-adamantyl)-1,3,4-thiadiazoline-2-one 16, were synthesized and tested for in vitro activities against a panel of gram-positive and gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7, 9, 15b and 15c displayed marked activity against the tested gram-positive bacteria, while compound 3 was highly active against the tested gram-negative bacteria. Compounds 4b, 7 and 15c were weakly or moderately active against C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats. The propionic acid derivative 9 produced good dose-dependent anti-inflammatory activity.
Kadi
Adnan A
AA
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia.
Al-Abdullah
Ebtehal S
ES
Shehata
Ihsan A
IA
Habib
Elsayed E
EE
Ibrahim
Tarek M
TM
El-Emam
Ali A
AA
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D013830:Thiadiazoles