Potential anticancer and antioxidant lauric acid-based hydrazone synthesis and computational study toward the electronic properties

Mohammed A Assiri; Akbar Ali; Muhammad Ibrahim; Muhammad Usman Khan; Khalid Ahmed; Muhammad Sajid Hamid Akash; Muhammad Akhtar Abbas; Athar Javed; Muhammad Suleman; Muhammad Khalid; Ishtiaq Hussain

doi:10.1039/d3ra02433d

Potential anticancer and antioxidant lauric acid-based hydrazone synthesis and computational study toward the electronic properties

RSC Adv. 2023 Jul 19;13(31):21793-21807. doi: 10.1039/d3ra02433d. eCollection 2023 Jul 12.

Authors

Affiliations

¹ Chemistry Department, Faculty of Science, King Khalid University P.O. Box 9004 Abha 61413 Saudi Arabia.
² Department of Chemistry, Government College University Faisalabad Faisalabad-38000 Pakistan.
³ Department of Applied Chemistry, Government College University Faisalabad Faisalabad-38000 Pakistan ibrahim@gcuf.edu.pk.
⁴ Department of Chemistry, University of Okara Okara-56300 Pakistan usman.chemistry@gmail.com usmankhan@uo.edu.pk.
⁵ H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi Karachi-75270 Pakistan.
⁶ Department of Pharaceutical Chemistry, Government College University Faisalabad Pakistan.
⁷ Department of Chemistry, Riphah International University Faisalabad Campus Pakistan.
⁸ Institute of Chemistry, Khwaja Fareed University of Engineering & Information Technology Rahim Yar Khan-64200 Pakistan.
⁹ Centre for Theoretical and Computational Research, Khwaja Fareed University of Engineering & Information Technology Rahim Yar Khan-64200 Pakistan.
¹⁰ Department of Pharmaceutical Sciences, Pak-Austria Fachhochschule Institute of Applied Sciences and Technology Mang Haripur Khyber Pakhtunkhwa Pakistan.

Abstract

The modification of natural products is one of the key areas of synthetic organic chemistry for obtaining valuable chemical building blocks that have medicinal significance. In this study, lauric acid-based hydrazones, namely (E)-N'-(2-nitrobenzylidene)dodecanehydrazide (NBDH), (E)-N'-(naphthalen-1-ylmethylene)dodecanehydrazide (NMDH), and (E)-N'-(4-fluorobenzylidene)dodecanehydrazide (FBDH), were synthesized and characterized using spectroscopic techniques. The newly synthesized lauric acid-based hydrazones were screened for their anticancer and antioxidant potential. The antioxidants showed their activity by inhibiting the oxidative chain reactions that produce reactive oxygen species. The antioxidant activity showed that NBDH exhibited the maximum DPPH inhibitory activity when compared with that of NMDH and FBDH, whereas the anticancer activity showed that FBDH exhibited maximum percent viability when compared to that of NBDH and NMDH. The reactivity and biological needs of the synthesized compounds NBDH, NMDH, and FBDH were met by performing geometrical, FT-IR vibrational, UV-visible, global reactivity parameters (GRP), MEP, FMO, NBO, ELF, LOL, and nonlinear optical (NLO) analysis at the DFT/B3LYP/6-311+G(d,p) level. NBO analysis confirmed the existence of extended conjugation and intramolecular charge transfer among NBDH, NMDH, and FBDH, which have the lowest gap in π → π*, which are in line with the FMO results where successful charge transfer occurred from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). GRP analysis confirmed the potential of NBDH, NMDH, and FBDH for biological, electronic, and NLO applications. It is clear from the comparative analysis of the urea molecule that NBDH, NMDH, and FBDH all comprise fine NLO properties.