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Synthesis and Biological Potentials of 5-aryl-N-[4-(Trifluoromethyl)Phenyl]-1,3,4-Oxadiazol-2-Amines

Author(s):

Mohamed Jawed Ahsan*, Mohd. Zaheen Hassan, Surender Singh Jadav, Mohammed H. Geesi, Mohammed Afroz Bakht, Yassine Riadi, Salahudiin, Md. Sayeed Akhtar, Mohammad Nasar Mallick and Habban Akhter  

Abstract:


Oxadiazoles are important class of heterocyclic compounds, having broad spectrum activity. They were also reported as anticancer, and antioxidant agents, hence it is of significant importance to explore new oxadiazoles. A series of eleven (5-aryl-N-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amines (6a-k) was synthesized based on the structures of reported compounds, SU-101, IMC38525, and FTAB. All these oxadiazoles were synthesized, characterized by spectral data, and further tested against melanoma, leukemia, colon, lung, CNS, ovarian, renal, breast and prostate cancer cell lines’ panels at a single dose of 10 µM drug concentrations. N-(4-(Trifluoromethyl)phenyl)-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-amine (6h) showed significant anticancer activity, and the most sensitive five cell lines were NCI-H522 (% GI = 53.24), K-562 (% GI = 47.22), MOLT-4 (% GI = 43.87), LOX-IMVI (% GI = 43.62), and HL-60(TB) (% GI = 40.30). The compound, 6i revealed better %GIs than imatinib, against 32 cell lines, taking 58 cell lines in common. The maximum sensitivity was recorded against cancer cell line CCRF-CEM (% GI = 68.89) by 2-(5-(4-(trifluoromethyl)phenylamino)-1,3,4-oxadiazol-2-yl)phenol (6f). The antioxidant activity of 4-(5-(4-(trifluoromethyl)phenylamino)-1,3,4-oxadiazol-2-yl)-2-methoxyphenol (6i) was promising with an IC50 of 15.14 µM. It was observed that the oxadiazoles reported herein showed significant anticancer, and antioxidant activities.

Keywords:

Anticancer, Antioxidants, DPPH assay, Oxadiazoles, One dose assay

Affiliation:

Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha 62529, , Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha 62529, , Department of Pharmaceutical Science & Technology, Birla Institute of Science & Technology, Mesra, Ranchi, Jharkhand 835 215,, Department of Chemistry, College of Science & Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box 11323, , Department of Chemistry, College of Science & Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box 11323, , Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdul Aziz University, P.O. Box 11323,, Department of Pharmaceutical Chemistry, Noida Institute of Technology (Pharmacy Institute), Knowledge Park-2, Greater Noida, Uttar Pradesh 201 306, , Department of Clinical Pharmacy, College of Pharmacy, King Khalid University, Abha 62529,, Department of Pharmacognosy, College of Pharmacy, King Khalid University, Abha 62529, , Faculty of Pharmacy, DIT University, Dehradun, Uttarakhand 248 009



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