Theoretical and experimental investigations on structural, electronic and biological properties of novel carbazate containing furaldehyde based imines

• Published in: Journal of molecular structure Vol. 1318; p. 139130
• Main Authors: Shaikh, Mohd Z., Shatat, Abdallah S., Bakar, Hamidah Abu, Kaur, Mandeep, Kaur, Harpreet, Al Khatib, Arwa O., Kumar, Ashish, Alhadrawi, Merwa, Prasad, G.V. Siva, Sinha, Aashna, Almutairi, Tahani M., Butcher, Raymond J., Bhat, Muzzaffar A.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.12.2024
• Subjects: DFT; Docking; Hirshfeld surface; PASS; Synthesis; X-ray; Docking; Synthesis; DFT; X-ray; PASS; Hirshfeld surface
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.139130

•A convenient and facile synthesis of carbazate based imines (a and b) were accomplished by refluxing t‑butyl/ethyl carbazate with furaldehyde in ethanol.•The presence of pi…pi and CH…Pi stacking interactions are distinguishing characteristic of crystal packing in both target compounds.•Hirshfeld surface analysis was also applied to discern the intermolecular interactions.•A theoretical foundation for the logical design of new carbazate compounds as substrate inhibitors for Harmone-sensitive lipases is provided by the docking data. A convenient and facile synthesis of tert‑butyl (E)-2-(furan-2-ylmethylene) hydrazine-1-carboxylate (a) and ethyl (E)-2-(furan-2-ylmethylene) hydrazine-1-carboxylate (b) were accomplished by refluxing t‑butyl/ethyl carbazate with a furaldehyde in solvent ethanol. The interactions between and within two synthesised imine compounds were characterised and identified by the utilisation of spectroscopic techniques in conjunction with X-ray crystallography and theoretical computations. Compound a crystallises in orthorhombic crystal system with Pbca space group, while as compound b crystalizes in monoclinic crystal systems with space groups Cc. The presence of CH…π stacking and π…π stacking interactions are distinguishing characteristic of crystal packing in both target compounds. Their solid-state behaviour was also studied using Hirshfeld surfaces. Crystal packing motifs were investigated with the aid of Hirshfeld surface fingerprint plots. Furthermore, investigations related to calculations of the molecular electrostatic potential and frontier molecular orbital (highest occupied-lowest unoccupied) were carried out for the optimised structure. Finally, Hormone-sensitive lipase (HSL) (PDB-ID 6KEU) protein was used to conduct molecular docking investigations of compound a and b. [Display omitted]