Synthesis of novel derivatives of 4-methylbenzimidazole and evaluation of their biological activities

  • Eur J Med Chem. 2014 Sep 12:84:731-8. doi: 10.1016/j.ejmech.2014.07.078.
Muhammad Taha  1 ,  Nor Hadiani Ismail  2 ,  Waqas Jamil  3 ,  Hesham Rashwan  4 ,  Syed Muhammad Kashif  3 ,  Amyra Amat Sain  5 ,  Mohd Ilham Adenan  6 ,  El Hassane Anouar  7 ,  Muhammad Ali  8 ,  Fazal Rahim  9 ,  Khalid M Khan  10
Affiliations
  • 1. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 43200 Puncak Alam, Selonger, Malaysia; Faculty of Applied Science UiTM, 40450 Shah Alam, Selangor D. E., Malaysia. Electronic address: [email protected].
  • 2. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 43200 Puncak Alam, Selonger, Malaysia; Faculty of Applied Science UiTM, 40450 Shah Alam, Selangor D. E., Malaysia.
  • 3. Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Pakistan.
  • 4. Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam 42300, Selangor, Malaysia.
  • 5. Malaysian Institute of Pharmaceuticals and Nutraceuticals, Ministry of Science, Technology and Innovation, Bangunan Pentadbiran, Blok 5-A, Halaman Bukit Gambir,11700 Bayan Lepas, Penang, Malaysia.
  • 6. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 43200 Puncak Alam, Selonger, Malaysia; Malaysian Institute of Pharmaceuticals and Nutraceuticals, Ministry of Science, Technology and Innovation, Bangunan Pentadbiran, Blok 5-A, Halaman Bukit Gambir,11700 Bayan Lepas, Penang, Malaysia; Forest Research Institute Malaysia (FRIM), 52109 Kepong, Selangor, Malaysia.
  • 7. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 43200 Puncak Alam, Selonger, Malaysia.
  • 8. Center for Advanced Drug Research, COMSATS Institute of Information Technology, University Road, Abbottabad 22060, KPK, Pakistan.
  • 9. Department of Chemistry, Hazara University, Mansehra, Pakistan.
  • 10. H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
PMID: 25069019 DOI: 10.1016/j.ejmech.2014.07.078
Abstract

4-Methylbenzimidazole 1-28 novel derivatives were synthesized and evaluated for their antiglycation and antioxidant activities. Compounds 1-7 and 11 showed excellent activities ranged 140-280 μM, better than standard drug rutin (294.46 ± 1.50 μM). Compound 1-28 were also evaluated for DPPH activities. Compounds 1-8 showed excellent activities, ranging 12-29 μM, better than standard drug n-propylgallate (IC50 = 30.30 ± 0.40 μM). For superoxide anion scavenging activity, compounds 1-7 showed better activity than standard n-propylgallate (IC50 = 106.34 ± 1.6 μM), ranged 82-104 μM. These compounds were found to be nontoxic to THP-1 cells.

Keywords
Antiglycation; Antileishmanial; Antioxidant; Benzimidazole; Stereoisomers.