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Please use this identifier to cite or link to this item: http://hdl.handle.net/123456789/2389

Title: Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4- oxadiazoline-2-thiones
Authors: El-Emam, Ali A.
Al-Deeb, Omar A.
Al-Omar, Mohamed
Lehmann, Jochen
Keywords: 1-adamantyl
Aminomethy
Anti-HIV-1
Antimicrobial
XTT
Issue Date: 2004
Publisher: Elsevier
Citation: Bioorganic & Medicinal Chemistry: 12; 5107–5113
Abstract: The reaction of 5-(1-adamantyl)-1,3,4-oxadiazoline-2-thione 2 with iodoethane, 2-dimethylaminoethyl chloride hydrochloride or 2-piperidinoethyl chloride hydrochloride in ethanolic potassium hydroxide yielded the corresponding 5-(1-adamantyl)- 2-ethyl or substituted ethylthio-1,3,4-oxadiazoles 3a–c. Interaction of 2 with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding 5-(1-adamantyl)-3-arylaminomethyl- 1,3,4-oxadiazoline-2-thiones 4a–m or 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-oxadiazoline-2-thiones 5a–h, respectively. All the synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gramnegative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 2, 5a, and 5e were found as the most active derivatives, particularly against the Gram-positive bacteria. In addition, the antiviral activity of compounds 2, 4a–m, and 5a–h against HIV-1 using the XTT assay was carried out. Compound 2 produced 100%, 43%, and 37% reduction of viral replication at 50, 10, and 2lg/mL concentrations, respectively.
Description: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University
URI: http://hdl.handle.net/123456789/2389
ISSN: 0968-0896
Appears in Collections:College of Pharmacy

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