Synthesis, QSAR and anti-HIV activity of new 5-benzylthio-1,3,4-oxadiazoles derived from α-amino acids

Journal of Enzyme Inhibition and Medicinal Chemistry
Tayyaba SyedShahid Hameed

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 EC(50) 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.

References

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Citations

Nov 9, 2011·Acta Crystallographica. Section E, Structure Reports Online·Tayyaba SyedPeter G Jones
Jan 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Tayyaba SyedPeter G Jones
Nov 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Muhammad FarmanTanveer Ahmad
Feb 10, 2017·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Patel NavinGildardo Rivera
Aug 15, 2012·Chemistry : a European Journal·Thi My Uyen TonPhilip Wai Hong Chan

Related Concepts

Antiviral Agents
HIV
Oxadiazoles
Sulfhydryl Compounds
Sulfonamides
Crystallography, X-Ray
Inhibitory Concentration 50
Quantitative Structure Property Relationship
Pharmacologic Substance

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