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Synthesis, crystal structure, DFT studies and evaluation of the antioxidant activity of 3,4-dimethoxybenzenamine schiff bases

Aziz AN 1 , Taha M 2 , Ismail NH 3 , Anouar el H 4 , Yousuf S 5 , Jamil W 6 Show all authors , Awang K 7 , Ahmat N 8 , Khan KM 9 , Kashif SM 10

Affiliations 

  • 1 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, 42300 Puncak Alam Campus, Malaysia. nazif_umt@yahoo.com
  • 2 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, 42300 Puncak Alam Campus, Malaysia. taha_hej@yahoo.com
  • 3 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, 42300 Puncak Alam Campus, Malaysia. noriz118@salam.uitm.edu.my
  • 4 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, 42300 Puncak Alam Campus, Malaysia. anouarelhassane@yahoo.fr
  • 5 Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, 75270 Karachi, Pakistan. dr.sammer.yousuf@gmail.com
  • 6 Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Hyderabad 76080, Pakistan. waqas143kh@yahoo.com
  • 7 Department of Chemistry, Faculty of Science, Universiti Malaya, 50603 Kuala Lumpur, Malaysia. khalijah@um.edu.my
  • 8 Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia. noriz118@salam.uitm.edu.my
  • 9 Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, 75270 Karachi, Pakistan. khalid.khan@iccs.edu
  • 10 Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Hyderabad 76080, Pakistan. hope_cancer@yahoo.com
Molecules, 2014 Jun 19;19(6):8414-33.
PMID: 24950444 DOI: 10.3390/molecules19068414

Abstract

Schiff bases of 3,4-dimethoxybenzenamine 1-25 were synthesized and evaluated for their antioxidant activity. All the synthesized compounds were characterized by various spectroscopic techniques. In addition, the characterizations of compounds 13, 15 and 16 were supported by crystal X-ray determinations and their geometrical parameters were compared with theoretical DFT calculations at the B3LYP level of theory. Furthermore, the X-ray crystal data of two non-crystalline compounds 8 and 18 were theoretically calculated and compared with the practical values of compounds 13, 15, 16 and found a good agreement. The compounds showed good DPPH scavenging activity ranging from 10.12 to 84.34 μM where compounds 1-4 and 6 showed stronger activity than the standard n-propyl gallate. For the superoxide anion radical assay, compounds 1-3 showed better activity than the standard.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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