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Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Antibacterial Agents

[ Vol. 18 , Issue. 5 ]

Author(s):

Em Canh Pham*, Tuyen Ngoc Truong*, Nguyen Hanh Dong, Duy Duc Vo and Tuoi Thi Hong Do   Pages 558 - 573 ( 16 )

Abstract:


<P>Background: Many compounds containing a five-membered heterocyclic ring display exceptional chemical properties and versatile biological activities. <P> Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4- oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibacterial and antifungal activities. <P> Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarbazones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by 1H-NMR, 13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. <P> Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. <P> Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecalis, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed antifungal activity against Candida albicans (8 μg/mL) and Aspergillus niger (64 μg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 μM) which is comparable to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds have also been reported.</P>

Keywords:

1,3,4-oxadiazole, 1,4-thiadiazole, antibacterial, antifungal, anticancer, molecular docking.

Affiliation:

Department of Organic Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh city, 700000 Ho Chi Minh city, Department of Organic Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh city, 700000 Ho Chi Minh city, Department of Organic Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh city, 700000 Ho Chi Minh city, Department of Chemistry, and Department of Cell and Molecular Biology, Uppsala University, Uppsala city, Department of Pharmacology, Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh city, 700000 Ho Chi Minh city



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