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Synthesis, Evaluation of Antioxidant Activity and Crystal Structure of 2,4-Dimethylbenzoylhydrazones
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam 42300, Selangor, Malaysia
Faculty of Applied Science Universiti Tecknologi MARA, Shah Alam 40450, Selangor, Malaysia
Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Hyderabad 76080, Pakistan
Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
* Author to whom correspondence should be addressed.
Received: 14 August 2013; in revised form: 2 September 2013 / Accepted: 4 September 2013 / Published: 5 September 2013
Abstract: 2,4-Dimethylbenzoylhydrazones 1–30 were synthesized by condensation reactions of 2,4-dimethylbenzoylhydrazide with various aromatic aldehydes and characterized. The assigned structures of compounds 10, 15 and 22 were further supported by single-crystal X-ray diffraction data. The synthesized compounds were evaluated for their in vitro DPPH radical scavenging activity. They exerted varying degree of scavenging activity toward DPPH radical with IC50 values between 25.6–190 µM. Compounds 1, 4, 2, 3, 7, and 6 have IC50 values of 25.6, 28.1, 29.3, 29.8, 30.0 and 30.1 µM respectively, showing better activity than an n-propyl gallate standard (IC50 value = 30.30 µM). For super oxide anion scavenging activity compounds 1, 2 and 3 with IC50 values of 98.3, 102.6, and 105.6, respectively, also showed better activity than the n-propyl gallate standard (IC50 value = 106.34 µM).
Keywords: 2,4-dimethylbenzoylhydrazones; DPPH scavenging; superoxide ion scavenger; crystal structure
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Taha, M.; Ismail, N.H.; Jamil, W.; Yousuf, S.; Jaafar, F.M.; Ali, M.I.; Kashif, S.M.; Hussain, E. Synthesis, Evaluation of Antioxidant Activity and Crystal Structure of 2,4-Dimethylbenzoylhydrazones. Molecules 2013, 18, 10912-10929.
Taha M, Ismail NH, Jamil W, Yousuf S, Jaafar FM, Ali MI, Kashif SM, Hussain E. Synthesis, Evaluation of Antioxidant Activity and Crystal Structure of 2,4-Dimethylbenzoylhydrazones. Molecules. 2013; 18(9):10912-10929.
Taha, Muhammad; Ismail, Nor H.; Jamil, Waqas; Yousuf, Sammer; Jaafar, Faridahanim M.; Ali, Muhammad I.; Kashif, Syed M.; Hussain, Ejaz. 2013. "Synthesis, Evaluation of Antioxidant Activity and Crystal Structure of 2,4-Dimethylbenzoylhydrazones." Molecules 18, no. 9: 10912-10929.