title: Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols.
abstract: The reaction of 5-(1-adamantyl)-4-phenyl-1,2,4-triazoline-3-thione (compound 5) with formaldehyde and 1-substituted piperazines yielded the corresponding N-Mannich bases 6a-f. The reaction of 5-(1-adamantyl)-4-methyl-1,2,4-triazoline-3-thione 8 with various 2-aminoethyl chloride yielded separable mixtures of the S-(2-aminoethyl) 9a-d and the N-(2-aminoethyl) 10a-d derivatives. The reaction of compound 5 with 1-bromo-2-methoxyethane, various aryl methyl halides, and ethyl bromoacetate solely yielded the S-substituted products 11, 12a-d, and 13. The new compounds were tested for activity against a panel of Gram-positive and Gram-negative bacteria and the pathogenic fungus Candida albicans. Compounds 6b, 6c, 6d, 6e, 6f, 10b, 10c, 10d, 12c, 12d, 12e, 13, and 14 displayed potent antibacterial activity. Meanwhile, compounds 13 and 14 produced good dose-dependent anti-inflammatory activity against carrageenan-induced paw edema in rats.
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, Riyadh, Saudi Arabia.
authors.forename: Ebtehal S
authors.initials: ES
authors.lastname: Al-Abdullah
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, Riyadh, Saudi Arabia.
authors.forename: Hanadi H
authors.initials: HH
authors.lastname: Asiri
authors.affiliation: Department of Chemistry, College of Sciences, King Saud University, Riyadh, Saudi Arabia.
authors.forename: Siham
authors.initials: S
authors.lastname: Lahsasni
authors.affiliation: Department of Pharmaceutics and Pharmaceutical Technology, College of Pharmacy, Taibah University, Medinah, Saudi Arabia.
authors.forename: Elsayed E
authors.initials: EE
authors.lastname: Habib
authors.affiliation: Department of Pharmacology and Toxicology, Faculty of Pharmacy, University of Mansoura, Mansoura, Egypt.
authors.forename: Tarek M
authors.initials: TM
authors.lastname: Ibrahim
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, Riyadh, Saudi Arabia.
authors.forename: Ali A
authors.initials: AA
authors.lastname: El-Emam
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D004305:Dose-Response Relationship, Drug; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D013438:Sulfhydryl Compounds; D014230:Triazoles
keywords: 1,2,4-triazoles; N-Mannich bases; adamantane derivatives; anti-inflammatory activity; antimicrobial activity