title: Synthesis and antimicrobial activity of N'-heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines.
abstract: The reaction of adamantane-1-carbohydrazide (1) with heterocyclic aldehydes, namely 5-(4-chlorophenyl)isoxazole-3-carboxaldehyde (2a), 5-(4-methylphenyl)isoxazole-3-carboxaldehyde (2b), 5-(4-methoxyphenyl)isoxazole-3-carboxaldehyde (2c), 1H-imidazole-2-carboxaldehyde and 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde, in ethanol, yielded the corresponding N'-heteroarylidene-1-adamantylcarbohydrazides 3a, 3b, 3c, 4 and 5, respectively, in good yields. The 4-acetyl-1,3,4-oxadiazoline analogues 6a‑c were prepared in 48-55% yields by heating their corresponding N'-heteroarylidene-1-adamantylcarbohydrazides 3a-c with acetic anhydride for two hours. Compounds 3a-c, 4, 5 and 6a-c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 4 and 5 displayed potent broad-spectrum antimicrobial activity, while compounds 3a-c showed good activity against the Gram-positive bacteria.
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia. aelemam@ksu.edu.sa
authors.forename: Ali A
authors.initials: AA
authors.lastname: El-Emam
authors.forename: Khalid A
authors.initials: KA
authors.lastname: Alrashood
authors.forename: Mohamed A
authors.initials: MA
authors.lastname: Al-Omar
authors.forename: Abdul-Malek S
authors.initials: AM
authors.lastname: Al-Tamimi
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D006834:Hydrazines; D007555:Isoxazoles; D010069:Oxadiazoles; C019289:carbohydrazide