4-(4-methoxyphenyl)-6-methyl-3-phenyl-4H-1,2,4-oxadiazin-5(6H)- one: Synthesis, crystal structure, Hirshfeld surface analysis, noncovalent, ADMET studies and biological evaluation

Oxadiazines are heterocyclic compounds containing two nitrogen and one oxygen atom in a six-membered ring. The synthesis and crystal structure of 4-(4-methoxyphenyl)-6-methyl-3-phenyl-4H-1,2,4-oxadiazin-5(6H)-one (MPMP-OXA) was reported. The organic crystal structure of the synthesized com-pound was fully characterized by various spectroscopic techniques (Fourier Transform Infrared Spec-troscopy, NMR and LC/MS-TOF) and single-crystal X-ray diffraction studies. The MPMP-OXA crystal struc-ture crystallizes in the triclinic system and space group P-1 with a = 5.9395(15) A, b = 11.471(3) A, c = 11.901(3) A, alpha = 70.075(4) degrees, beta = 83.454(4) degrees, gamma = 78.016(4) degrees, V = 744.9(3) A3, Z = 2 cell parameters. This work is aimed to study the weak interactions in the crystal packing of a new synthesized oxadi-azine derivate. The contributions of the most important intermolecular interactions in the crystal struc-ture were investigated by 3D-Hirshfeld surface (HS) and 2D-fingerprint analysis. The C -H center dot center dot center dot O interactions as the most important contributors to the crystal packing between the oxygen of the oxadiazine ring and the hydrogen atom of phenyl ring appear as bright red spots visible on the HS surface. The hydrogen-bonded interaction of MPMP-OXA has been investigated using noncovalent interactions approach. The molecular docking studies for the synthesized compound were performed to gain insight into the inhibi-tion nature of this molecule against DNA Gyrase B Candida and 3-chymotrypsin-like protease (SARS-CoV main protease) proteins and resulted in good activities for new anti-agents. Lastly, Bioavailability, drug-gability as well as absorption, distribution, metabolism, excretion, and toxicity parameters (ADMET), and gastrointestinal absorption (BOILED-Egg method) properties of newly synthesized compound using smile codes were performed in detail.(c) 2023 Elsevier B.V. All rights reserved.

Automated summary

This study reports the synthesis and crystal structure of 4-(4-methoxyphenyl)-6-methyl-3-phenyl-4H-1,2,4-oxadiazin-5(6H)-one. The organic crystal structure was characterized using various spectroscopic techniques and X-ray diffraction studies. The most important intermolecular interactions in the crystal structure were investigated, and the inhibitory activities of the synthesized compound against DNA Gyrase B Candida and 3-chymotrypsin-like protease proteins were studied.