T. Syed, Tashfeen Akhtar, N. Al-Masoudi
Sep 14, 2011
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Journal
Journal of Enzyme Inhibition and Medicinal Chemistry
Abstract
2-(1-[(4-Chloro/methylphenylsulfonylamino)alkyl]-5-thioxo-4,5-dihydro-1,3,4-oxadiazoles (4a–e) were synthesized, in four steps, via the sulfonyl derivatives of l-amino acids (l-alanine, l-methionine and l-phenylalanine) 1a–e, the esters 2a–e, the hydrazides 3a–e and finally the cyclization to 4a–e. Alkylation of 4a–e with 1.0 mole eq. of substituted benzyl halides furnished S-benzyl derivatives 5a–t, while 1.1 mole eq. yielded major 5a–t and minor amount of 6a–d. Alternatively, treatment of 4a–e with 2.0 mole eq. of substituted benzyl halides furnished 6a–d only. The structures of 5b and 5l were further confirmed by single crystal X-ray analysis. Compounds 5a–t and 6a–d showed no selective inhibition against HIV-1 and HIV-2 replication in MT-4 cells. However, 5f and 5j–5q exhibited some inhibitory activity against both types with EC50 values (>11.50 − >13.00 µg/mL). These results suggest that the structural modifications of these compounds might lead to the development of new antiviral agents. The quantum structure-activity relationship of these novel structural congeners is discussed.