Journal
STEROIDS
Volume 72, Issue 5, Pages 459-465Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2007.01.003
Keywords
alpha-oxoketene dithioacetal; pyrimidine; thiophene; benzoimidazole; antibacterial; androstane
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This study aimed at the synthesis of novel structurally promising steroidal heterocycles and to elucidate the potential role of these compounds as antibacterial agents. Epi-androsterone 1 reacted with CS2 and sodium hydride in dimethylsulfoxide to yield alpha-oxoketene dithiodisodium salt 2. The non-isolable salt 2 reacted with acetyl chloride, benzoyl chloride, phenacyl bromide and iodometiane to afford the corresponding alpha-oxodithioacetal derivatives 4a,b, 6 and 7, respectively. Interaction of 2 with the alkyl halide reagents 8a-d yielded the corresponding thiophene derivatives 10a-d. alpha-Oxoketene dithioacetal 7 reacted with urea and thiourea to furnish the pyrimidinoandrostane derivatives 12a,b. Compound 7 also reacted with ortho-phenylene diamine and ortho-aminophenol 13a,b to produce the dinucleophilic adducts 15a,b. The in vitro antibacterial evaluation of some newly prepared compounds showed that all compounds have high significant antibacterial activity against the used strains of Gram positive and Gram negative bacteria. (c) 2007 Elsevier Inc. All rights reserved.
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