A Schiff Base with Polymorphic Structure (Z '=2): Investigations with Computational Techniques and in Silico Predictions

Şahin S., Can N. N.

POLYCYCLIC AROMATIC COMPOUNDS, vol.43, no.10, pp.9269-9294, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 10
  • Publication Date: 2023
  • Doi Number: 10.1080/10406638.2022.2161585
  • Journal Name: POLYCYCLIC AROMATIC COMPOUNDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Page Numbers: pp.9269-9294
  • Keywords: SARS-CoV-2, Schiff base, polymorphic crystal, ADME, docking, FINGERPRINT SIMILARITY SEARCH, CRYSTAL-STRUCTURE, HIRSHFELD SURFACE, BIOLOGICAL EVALUATION, MOLECULAR-STRUCTURE, DRUG DISCOVERY, SOLID-STATE, DFT, DOCKING, ABSORPTION
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In this study, we report a newly synthesized Schiff base molecule named (E)-N-(2-chloropyridin-3-yl)-1-(5-nitro-2-(piperidin-1-yl)phenyl)methanimine. We also report its structural, chemical, surface, and electronic properties, potential targets, drug-likeness, ADME and toxicity profile, and docking studies for the main protease (Mpro) of SARS-CoV-2. The scope of this study includes the topological and electronic properties, intermolecular interactions, physicochemical and pharmacokinetic properties, metabolic pathways, toxicity endpoints, blood-brain barrier (BBB) permeability, and intestinal absorption activities. We performed the above analyses using bioinformatics/chemoinformatics tools and computational techniques. The topic crystal/compound (TC) contains two crystallographically independent molecules in the asymmetric unit (Z' = 2). TC is open to attack by electrophilic and nucleophilic species and is a soft, chemically reactive, kinetically unstable material. There are no deviations from the known drug-likeness rules. BBB penetration and GI absorption of TC are possible. The docking values of the complex Mpro/TC and Mpro/native ligand N3 were calculated to be -8.10 and -7.11 kcal/mol, respectively. Therefore, we can say that TC is a potential Mpro inhibitor and can be investigated for further laboratory studies.