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Open AccessArticle

1,3,4-Oxadiazole N-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities

1
Department of Chemistry, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia
2
Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
3
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
4
Department of Pharmacology and Biochemistry, Faculty of Pharmacy, Delta University for Science and Technology, International Costal Road, Gamasa City, Mansoura 11152, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Athina Geronikaki
Molecules 2021, 26(8), 2110; https://doi.org/10.3390/molecules26082110
Received: 5 March 2021 / Revised: 29 March 2021 / Accepted: 31 March 2021 / Published: 7 April 2021
(This article belongs to the Special Issue Biologically Active Heterocyclic Compounds)
The reaction of 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thione 3 with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding N-Mannich bases 3-arylaminomethyl-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thiones 4al or 3-[(4-substituted piperazin-1-yl)methyl]-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thiones 5ad, respectively. The in vitro inhibitory activity of compounds 4al and 5ad was assessed against pathogenic Gram-positive, Gram-negative bacteria, and the yeast-like pathogenic fungus Candida albicans. The piperazinomethyl derivatives 5c and 5d displayed broad-spectrum antibacterial activities the minimal inhibitory concentration (MIC) 0.5–8 μg/mL) and compounds 4j, 4l, 5a, and 5b showed potent activity against the tested Gram-positive bacteria. In addition, the anti-proliferative activity of the compounds was evaluated against prostate cancer (PC3), human colorectal cancer (HCT-116), human hepatocellular carcinoma (HePG-2), human epithelioid carcinoma (HeLa), and human breast cancer (MCF7) cell lines. The optimum anti-proliferative activity was attained by compounds 4l, 5a, 5c, and 5d. View Full-Text
Keywords: 1,3,4-oxadiazoles; N-Mannich bases; antimicrobial activity; anti-proliferative activity 1,3,4-oxadiazoles; N-Mannich bases; antimicrobial activity; anti-proliferative activity
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MDPI and ACS Style

Al-Wahaibi, L.H.; Mohamed, A.A.B.; Tawfik, S.S.; Hassan, H.M.; El-Emam, A.A. 1,3,4-Oxadiazole N-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities. Molecules 2021, 26, 2110. https://doi.org/10.3390/molecules26082110

AMA Style

Al-Wahaibi LH, Mohamed AAB, Tawfik SS, Hassan HM, El-Emam AA. 1,3,4-Oxadiazole N-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities. Molecules. 2021; 26(8):2110. https://doi.org/10.3390/molecules26082110

Chicago/Turabian Style

Al-Wahaibi, Lamya H.; Mohamed, Ahmed A.B.; Tawfik, Samar S.; Hassan, Hanan M.; El-Emam, Ali A. 2021. "1,3,4-Oxadiazole N-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities" Molecules 26, no. 8: 2110. https://doi.org/10.3390/molecules26082110

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