Green Route Synthesis and Molecular Docking of Azines Using Cellulose Sulfuric Acid under Microwave Irradiation

Abstract

A novel catalytic approach for the synthesis of symmetric and asymmetric azines has been developed. The environmentally benign protocol was achieved via condensation of 1-[(2-thienyl)ethylidene]hydrazine (1) with different aromatic aldehydes 2a–h and acetyl heterocyclic compounds (4, 6, 8, 10, and 12) in the presence of cellulose sulfuric acid (CSA) as the green catalyst. These procedures offer an interesting method for the large-scale industrial manufacture of azines due to their high percentage yield, mild reaction conditions, broad substrate range, and utilization of an economical and environmentally acceptable catalyst. Additionally, the molecular docking of the products to the monoamine oxidase (MAO-A) target protein was achieved to highlight the possible binding interaction with the amino acid residues Arg51, Glu43, Gly22, Gly49, Gly443, Ala272, Ile335, and Tyr407 at the point of binding. The binding interaction energy was discovered to be (− 6.48 kcal/mol) for the protein MAO-A (PDB ID: 2Z5X). The most effective azine derivatives 7 and 13 revealed some major conserved interactions between the MAO-A protein’s binding site amino acid residues and the PDB co-crystal ligand 2Z5X. Moreover, azine derivatives 3a and 3f showed the lowest binding activity with the target MAO-A.

Green Biocatalyst for Ultrasound-Assisted Thiazole Derivatives: Synthesis, Antibacterial Evaluation, and Docking Analysis

“…Anticipated benefits such as enhanced renal excretion and reduced toxicity are linked to lower molecular weight and lipophilicity in molecules, which in turn lead to improved para-cellular and trans-cellular absorption characteristics. − Adhering to the 'rule of 5 (Ro5)' standards designates a compound as drug-like, requiring a molecular mass below 500, a log Po/w value under 5, and less than 5 hydrogen bond donors along with 10 acceptors. , As per the Veber rule, molecules with no more than 10 rotatable bonds, a polar surface area of 140 or less, and 12 or fewer hydrogen bond donors and acceptors demonstrate heightened oral bioavailability . These criteria play a significant role in a molecule’s absorption, distribution, metabolism, excretion, and toxicity (ADMET) profile .…”

Investigation of Newly Synthesized Fluorinated Isatin-Hydrazones by In Vitro Antiproliferative Activity, Molecular Docking, ADME Analysis, and e-Pharmacophore Modeling

“…Hydrazones, which are employed in diverse domains of organic chemistry, are renowned for their versatility and are recognized as a significant category of compounds for new drug development . Hydrazones, which are regarded as a significant group of organic compounds, encompass CN bonds that are conjugated with the lone pair of electrons of a functional nitrogen atom, and possess the structure R 1 R 2 CNNH 2 , Nitrogen atoms exhibit nucleophilic properties, whereas carbon atoms possess both electrophilic and nucleophilic characteristics. , Hydrazone linkages in pharmaceutical materials have significant value in numerous transformations and have attracted great interest because of their many biological and clinical applications, such as anticancer, antimicrobial, antioxidant, antituberculosis, anti-inflammatory, antiviral, antiproliferative, and enzyme inhibitory activities. − …”

Mechanochemical Synthesis and Molecular Docking Studies of New Azines Bearing Indole as Anticancer Agents

“…Bearing the aforementioned in mind, and in the framework of our ongoing research on the synthesis of bioactive heterocyclic derivatives [42,[50][51][52][53][54][55][56][57][58][59], the goal of the present study is the green synthesis of some new aldazine and ketazine derivatives, starting with 3-(1-hydrazineylideneethyl)-1H-indole and the evaluation of their potential anticancer activities, which was further supported by molecular docking studies using EFP as a native ligand [48,49]. In addition, the drug-likeness as well as SAR analysis of the reported derivatives were also investigated.…”