DABCO-PEG ionic liquid catalyzed synthesis, single-crystal structure, and antioxidant activity of a flavanone derivative
Syeda Abida Ejaz,
Bilal Ahmad Khan,
Pervaiz Ali Channar,
Mubashir Aziz,
Ehsan Ullah Mughal,
Aamer Saeed,
Laila Sumreen,
Zahid Hussain,
Mumtaz Hussain,
Rabail Ujan,
Muawya Elhadi,
Amina Sadiq,
Tuncer Hökelek
Affiliations
Syeda Abida Ejaz
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan
Bilal Ahmad Khan
Department of Chemistry, University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan
Pervaiz Ali Channar
Department of Basic Sciences and Humanities, Faculty of Information Science and Humanities, Dawood University of Engineering and Technology, Karachi 74800, Pakistan
Mubashir Aziz
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan
Ehsan Ullah Mughal
Department of Chemistry, University of Gujrat, Gujrat 50700, Pakistan
Aamer Saeed
Department of Chemistry, Quaid-i-Azam University, 45320 Islamabad, Pakistan
Laila Sumreen
Department of Homoeopathic Medical Sciences, Faculty of Medicine and Allied Health Sciences, The Islamia University of Bahawalpur, Bahawalpur, Pakistan
Zahid Hussain
Department of Chemistry, University of Karachi, Karachi 75270, Pakistan
Mumtaz Hussain
Department of Chemistry, University of Karachi, Karachi 75270, Pakistan
Rabail Ujan
Dr. M. A. Kazi Institute of Chemistry, University of Sindh, Jamshoro, Pakistan
Muawya Elhadi
Department of Physics, Faculty of Science and Humanities, Shaqra University, Ad-Dawadimi 11911, P.O. Box 1040, Shaqra, Saudi Arabia
Amina Sadiq
Department of Chemistry, Government College Women University, Sialkot 51300, Pakistan
Tuncer Hökelek
Department of Physics, Faculty of Engineering, Hacettepe University, Beytepe, Ankara 06800, Türkiye
Globally, the occurrence of skin cancers has been increasing day by day due to unprotected skin and exposure to UV radiation. This research is focused toward the evaluation of the antioxidant potential of an OH-free flavanone derivative that was synthesized by using 1,4-diazabicyclo[2.2.2]octane–polyethylene glycol (DABCO-PEG) 400. Ionic liquid was prepared via the alkylation of DABCO using 1-pentyl bromide followed by mixing with PEG 400. The structure of the synthesized molecules was characterized through single-crystal XRD. The target flavanone, viz., 2-(4-isobutylphenyl)chroman-4-one, was subjected to free radical activity. In addition, in silico studies were carried out with proteins ribonucleotide reductase and tyrosinase and isobutyl containing flavanone, viz., 2-(4-isobutylphenyl)chroman-4-one. The flavanone 2-(4-isobutylphenyl)chroman-4-one showed significant inhibition at a concentration of 25 μg/ml compared to vitamin C, which was also supported by the molecular docking studies. The flavanones exhibit binding energies of −6.45 and −6.83 kcal/mol for ribonucleotide reductase and tyrosinase, respectively. The results were further validated by molecular dynamic simulations, which recommended that further investigation of this flavanone must be carried out before using it in potent drug discovery in the field of skin cancer.
