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, Salahuddin, Md. Sayeed Akhtar, Mohammad Nasar Mallick, Md. Habban Akhter.

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 2 , 2020

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Abstract:

Oxadiazoles are an 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, 6h revealed better %GIs than imatinib, against 36 cell lines, taking 54 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, heterocyclic compounds.

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Article Details

VOLUME: 17
ISSUE: 2
Year: 2020
Page: [133 - 140]
Pages: 8
DOI: 10.2174/1570178616666190401193928
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