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Z. Naturforsch. 2012,
67b, 747 – 758
doi:10.5560/ZNB.2012-0095
New Aryl-1,3-thiazole-4-carbohydrazides, Their 1,3,4-Oxadiazole-2-thione, 1,2,4-Triazole, Isatin-3-ylidene and Carboxamide Derivatives. Synthesis and Anti-HIV Activity
1 Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan
2 Department of Chemistry, Mirpur University of Science and Technology (MUST), 10250 Mirpur, AJK, Pakistan
3 Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq
Reprint requests to Prof. Dr. S. Hameed. E-mail:
shameed@qau.edu.pk or Prof. Dr. N. A. Al-Masoudi. E-mail:
najim.al-masoudi@gmx.de
Received April 2, 2012 / published online July 18, 2012
A series of isatin-3-ylidene (6a–i) and arylthiazolyl-1,3,4-oxadiazole-2-thione derivatives 7a–i derived from arylthiazolyl carbohydrazide analogs 4a–i were synthesized. Analogously, coupling of 4f with various amino acid methyl esters in the presence of HOBt/DCC reagents afforded the carboxamide derivatives 9a–d. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. All compounds are inactive, except compounds 9b and 9c which showed inhibition of HIV-1 with EC50 = 2.34 μg mL−1, and 1.12 μg mL−1 with therapeutic indexes (SI) of 9 and <1, respectively.
Key words: anti-HIV Activity, Amino Acids, Imine Derivatives, Oxadiazoles, Thiazoles