Design and syntheses of 7-nitro-2-aryl-4H-benzo[d][1,3]oxazin-4-ones as potent anticancer and antioxidant agents

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Ayesha Bari
  • Zulfiqar Ali Khan
  • Sohail Anjum Shahzad
  • Syed Ali Raza Naqvi
  • Hira Amjad
  • Ahsan Iqbal
  • Muhammad Yar

Related Research Unit(s)

Detail(s)

Original languageEnglish
Article number128252
Journal / PublicationJournal of Molecular Structure
Volume1214
Online published13 Apr 2020
Publication statusPublished - 15 Aug 2020

Abstract

A group of new nitro substituted benzoxazinones (3a-k) were synthesized from easily available 4-nitroanthranilic acid. All the synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. Anti-proliferative and pro-apoptotic potential of all the synthesized compounds (3a-k) was evaluated by MTT and Hoechst 33258 staining assay respectively whereas their antioxidant properties were determined via DPPH free radical scavenging assay. The most active compounds (3a, 3c and 3k) showed significant cytotoxic potential against HeLa cells with an inhibition of cell viability that ranged between 28.54 and 44.67% (P < 0.001). Albeit statistically different, the anti-proliferative effect of 3c was in close match with that of the reference drug doxorubicin. Likewise, the test compounds showed profound pro-apoptotic potential with an apoptotic index that ranged between 52.86 and 75.61%. Besides, the docking studies revealed a higher efficiency for compounds (3a and 3h) owing to their better affinity and inhibition constant (Ki = 4.397 and 3.713 nmol) respectively. The antioxidant potential of synthesized benzoxazinones (3a-k) was in close agreement with the experimental anticancer results with a percent inhibition from 34.45 to 85.93% as compared to standard (90.56%).

Research Area(s)

  • Benzoxazin-4-ones, DPPH free radical scavenging assay, Human cervical carcinoma

Citation Format(s)

Design and syntheses of 7-nitro-2-aryl-4H-benzo[d][1,3]oxazin-4-ones as potent anticancer and antioxidant agents. / Bari, Ayesha; Khan, Zulfiqar Ali; Shahzad, Sohail Anjum et al.
In: Journal of Molecular Structure, Vol. 1214, 128252, 15.08.2020.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review