1. 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
- Author
-
Ricard Simon, Thakur Sharad, Kumar Dharmendra, Punetha Meeti, Ben Hmid Rim, Sharma Aashish, Morris Andrew, Singh Karanvir, Duc Vo Duy, Thi Hong Do Tuoi, A. Rodriguez Eric, Alam Khan Shah, Kuotsu Vineichuno, Billa Nashiru, Casault Paméla, Bansal Sonu, Abidi Wajih, Hanh Dong Nguyen, K. Yamamoto Bryan, Sonnet Pascal, L. Selokar Naresh, K. Bajwa Kamlesh, Paul Joyson, Ngoc Truong Tuyen, Dua Seema, Abdelkader Hamad Fatimetou, Dassonville-Klimpt Alexandra, Vijay Tirpude Narendra, Canh Pham Em, Sreedharan Nair Rajesh, Kumar Arbind, Daoust Benoit, Pal Rohit, Yadav P.S., Tisnerat Camille, Jawaid Akhtar Md, Kumar Pradeep, Parashar Atul, Lamiri Nadia, Achour Radhouane, Trabelsi Dekhra, Javed Naim Mohd., Kumar Sanjay, and Gosselet Fabien
- Subjects
Oxadiazoles ,Semicarbazide ,Antifungal Agents ,Molecular Structure ,biology ,Aspergillus niger ,Oxadiazole ,Microbial Sensitivity Tests ,biology.organism_classification ,Combinatorial chemistry ,Anti-Bacterial Agents ,Molecular Docking Simulation ,Structure-Activity Relationship ,chemistry.chemical_compound ,chemistry ,Thiadiazoles ,Drug Discovery ,Structure–activity relationship ,MTT assay ,Candida albicans ,Antibacterial activity ,IC50 - Abstract
Background: Many compounds containing a five-membered heterocyclic ring display exceptional chemical properties and versatile biological activities. 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. 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. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. 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.
- Published
- 2022