

Design, synthesis and molecular docking studies of some morpholine linked thiazolidinone hybrid molecules
Javeed Ahmad War (1)



(1) Synthetic Organic Chemistry-Molecular Modelling Laboratory, Department of Chemistry, Dr. Hari Singh Gour University, Sagar, Madhya Pradesh, 470003, India
(2) Synthetic Organic Chemistry-Molecular Modelling Laboratory, Department of Chemistry, Dr. Hari Singh Gour University, Sagar, Madhya Pradesh, 470003, India
(3) Synthetic Organic Chemistry-Molecular Modelling Laboratory, Department of Chemistry, Dr. Hari Singh Gour University, Sagar, Madhya Pradesh, 470003, India
(*) Corresponding Author
Received: 16 Mar 2016 | Revised: 10 Apr 2016 | Accepted: 17 Apr 2016 | Published: 30 Sep 2016 | Issue Date: September 2016
Abstract
A novel series of morpoline linked thiazolidione hybrid molecules targeting bacterial enoyl acyl carrier protein (Enoyl-ACP) reductase were designed and synthesized through a three step reaction protocol, which involves simple reaction setup and moderate reaction conditions. The synthesized molecules were characterized with FT-IR, 1H NMR, 13C NMR and HRMS techniques. In vitro susceptibility tests against some Gram positive (Staphylococcus aureus and Bacillus subtilis) and Gram negative bacteria (Escherichia coli and Pseudomonas aeruginosa) gave highly promising results. Most of the molecules were found to be active against the tested bacterial strains. The most potent molecule (S2B7) gave MIC value of 2.0 µg/mL against Escherichia coli that was better than the reference drug streptomycin. Structure activity relationship showed nitro and chloro groups are crucial for bioactivity if present at meta position of arylidene ring in designed molecules. Molecular docking simulations against multiple targets showed that the designed molecules have strong binding affinity towards Enoyl-ACP reductase. Binding affinity of -8.6 kcal/mol was predicted for S2B7. Van der Waals forces, hydrogen bonding and hydrophobic interactions were predicted as the main forces of interaction.
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DOI: 10.5155/eurjchem.7.3.271-279.1427
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Funding information
Department of Science and Technology, New-Delhi, India under INSPIRE program (INSPIRE ID: IF120399)
Citations
[1]. Javeed Ahmad War, Santosh Kumar Srivastava
Rationale design and synthesis of some novel imidazole linked thiazolidinone hybrid molecules as DNA minor groove binders
European Journal of Chemistry 11(2), 120, 2020
DOI: 10.5155/eurjchem.11.2.120-132.1974

[2]. Tarik E. Ali, Mohammed A. Assiri, Maha N. Alqahtani, Ali. A. Shati, Mohammad. Y. Alfaifi, Serag. E. I. Elbehairi
Recyclization of morpholinochromonylidene–thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives
RSC Advances 13(27), 18658, 2023
DOI: 10.1039/D3RA02777E

[3]. Ahmad Fawzi Qarah, Kahdr Alatawi, Adel I. Alalawy, Rua B. Alnoman, Alaa M. Alqahtani, Matokah M. Abualnaja, Wael M. Alamoudi, Nashwa M. El-Metwaly
Synthesis of phenylthiourea-based pyrazole, thiazole and/or pyran compounds: molecular modeling and biological activity
Journal of Taibah University for Science 17(1), , 2023
DOI: 10.1080/16583655.2023.2245200

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