Synthesis, DFT, in silico anticancer, ADME and toxicity prediction study of (E)-2-(2-(3,4-dihydronaphthalen-1(2H)- ylidene)hydrazineyl)-4-(4-methoxyphenyl)thiazole

Abstract

In the current paper, we describe computational molecular modeling to investigate the quantum chemical, spectroscopic, MESP and in-silico Anticancer, ADME and toxicity study of (E)-2-(2-(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazineyl)-4-(4-methoxyphenyl)thiazole by one pot three component reaction. DFT method with B3LYP/6-311G(d,p) level was used to optimize the geometry, molecular electrostatic potential (MESP), Mulliken charges and vibrational assignments. The UV-Vis assignments, frontier molecular orbital (FMO), electronic parameters, and global descriptor were studied using the TD-DFT method with CAM-B3LYP/6-311G(d,p) level. In-silico anticancer study revealed favorable binding interaction with an excellent docking score comparable to the anticancer drug Dasatinib. The molecular docking study found that, target 4xt2 receptor’s amino acid residues VAL422B, LEU407D, MET426D, TYR327A, GLN421B, SER424B, and LEU423D play a vital role. The title compound has the requisite toxicity and ADME profiles, and it has the potential to be therapeutic.

RESEARCH HIGHLIGHTS

• One pot synthesis of (E)-2-(2-(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazineyl)-4-(4-methoxyphenyl)thiazole

• Computational insights into structural analysis, HOMO-LUMO, electronic parameters, spectroscopic (UV-Vis and IR), MESP, and Mulliken charges.

• In silico anticancer study revealed favorable binding interaction with a docking score of -65.34

• Favorable ADME and toxicity profile of the studied compound.

GRAPHICAL ABSTRACT

Keywords:

• Computational
• molecular dyanmic simulations
• 2-hydrazinyl thiazole
• anticancer

Acknowledgment

Authors gratefully acknowledge CIF, SPPU, Pune for FT-IR and NMR characterization of samples. The authors also would like to thank Loknete Vyankatrao Hiray Arts, Science and Commerce College Panchavati,Nashik and Arts, Science and Commerce College, Manmad for providing necessary research facilities.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The authors disclosed that they did not receive any grants from funding agencies for the current study endeavor, which is entirely self-funded.