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Synthesis, Antiproliferative, and Antioxidant Activities of Substituted N-[(1,3,4-Oxadiazol-2-yl) Methyl] Benzamines

[ Vol. 17 , Issue. 2 ]

Author(s):

Mohamed Jawed Ahsan*, Lakshya Bhandari, Shally Makkar, Rajan Singh, Mohd. Zaheen Hassan, Mohammed H. Geesi, Mohamed Afroz Bakht, Surender Singh Jadav, Tuniki Balaraju, Yassine Riadi , Sandhya Rani, Habibullah Khalilullah, Vasubabu Gorantla and Afzal Hussain   Pages 145 - 154 ( 10 )

Abstract:


Background: Oxadiazole emerged as an important class of heterocyclic compound with diverse biological activities like anticancer, antitubercular, anticonvulsant, anti-tubulin, antimicrobial, anti-inflammatory, antioxidant etc.

Objective: The objective of this study is to synthesis series of twelve substituted N-[(1,3,4-oxadiazol-2- yl)methyl]benzamines (6a-l) and their evaluation as antiproliferative and antioxidant agents.

Methods: The substituted N-[(1,3,4-oxadiazol-2-yl)methyl]benzamines (6a-l) analogues were synthesized as per the reported procedure. The antiproliferative activity was tested against nine different panels cancer cell lines (leukemia, colon, renal, non-small cell lung, breast, CNS, melanoma, prostate, and ovarian cancer) at 10 µM drug concentrations as per the NCI US Protocol.

Results: 2-(5-((3-Chloro-4-fluorophenylamino)methyl)-1,3,4-oxadiazol-2-yl)phenol (6e) revealed the significant antiproliferative activity among the series of title compounds (6a-l). The compound, 6e showed maximum sensitivity towards CCRF-CEM, MCF-7, MOLT-4, T-47D, and SR cell lines with percent growth inhibitions (%GIs) of 79.92, 56.67, 39.62, 34.71 and 33.35, respectively. Furthermore, the compounds, 6e and 6c showed promising antioxidant activity with an IC50 value of 15.09 and 19.02 µM, respectively in DPPH free radicals (FR) scavenging activity.

Conclusion: The present study may support a significant value in cancer drug discovery programme.

Keywords:

Anti-proliferative agents, antioxidants, oxadiazoles, one dose assay, DPPH, free radicals scavenging activity.

Affiliation:

Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha 62529, Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha 62529, 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, Vishnu Institute of Pharmaceutical Education and Research (VIPER), Narsapur 502 313, Department of Pharmaceutical Science, Indian Institute of Science Education & Research, Kalyani, Nadia, Kolkatta, West Bengal 741 252, Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, P.O. Box- 173, Al-Kharj 11942, University Polytechnic BIT Mesra, Ranchi, Jharkhand 835 215, Department of Pharmaceutical Chemistry, Unaizah College of Pharmacy, Qassim University, Al-Qassim 51911, Department of Engineering Chemistry, AUCE(A), Andhra University, Andhra Pradesh 530 003, Department of Pharmaceutical Science & Technology, Birla Institute of Science & Technology, Mesra, Ranchi, Jharkhand 835 215

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