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Vol. 35 No. 6 (2023): Vol 35 Issue 6, 2023

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Cu(II) and Fe(III) Catalyzed Synthesis of Novel Thiophene Hybridized Thiadiazolyl Schiff Bases (TTS) as COX-2 Selective Inhibitor

https://doi.org/10.14233/ajchem.2023.27745
Geeta Mishra
Amity Institute of Pharmacy, Lucknow, Amity University Uttar Pradesh, Sector-125, Noida-201313, India Faculty of Pharmacy, Babu Banarasi Das Northern India Institute of Technology, Lucknow-226028, India
https://orcid.org/0000-0001-5118-2594
Parmesh K. Dwivedi
Amity Institute of Pharmacy, Lucknow, Amity University Uttar Pradesh, Sector-125, Noida-201313, India
https://orcid.org/0000-0002-6269-2810
Neeraj Verma
Hygia College of Pharmacy, Lucknow-226013, India
https://orcid.org/0000-0002-7037-6121
Sajal Srivastava
Amity Institute of Pharmacy, Lucknow, Amity University Uttar Pradesh, Sector-125, Noida-201313, India
https://orcid.org/0000-0003-2060-981X
Ashok K Singh
Amity Institute of Pharmacy, Lucknow, Amity University Uttar Pradesh, Sector-125, Noida-201313, India
https://orcid.org/0000-0002-4853-2028
Devdutt Chaturvedi
Department of Chemistry, School of Physical Sciences, Mahatma Gandhi Central University, Motihari-845401, India
https://orcid.org/0000-0003-0117-8698

Corresponding Author(s) : Parmesh K. Dwivedi

pkdwivedi@lko.amity.edu; parmeshdwivedi@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 6 (2023): Vol 35 Issue 6, 2023

Abstract

A novel series of thiophene hybridized thiadiazolyl Schiff bases (TTS) were designed and synthesized using copper nitrate (CuII) catalyzed synthesis of Schiff bases and their subsequent ferric chloride (FeIII) catalyzed cyclization into thiadiazoles. The design of molecules was inspired by the well-documented anti-inflammatory properties of thiadiazoles, Schiff bases and thiophene. Based on information from mass spectroscopy, IR, 1H and 13C NMR measurements, the structures of the recently synthesized compounds were determined. The purpose of molecular docking was to better understand the interactions between drug candidates and COX-1 (PDB ID: 3KK6) and COX-2 (PDB ID: 3Q7D) inflammation-related targets. Compounds 3a-f showed a more stable binding complex with COX-2 (-8.09 to -9.13 kcal/mol) when compared to COX-1 (-4.86 to -5.94 kcal/mol). Additionally, the carrageenan-induced rat paw oedema model was used for the in vivo analysis and compound 3a demonstrated excellent anti-inflammatory activity when compared to the reference drug, diclofenac. Interestingly, the mRNA expression analysis using qRT-PCR demonstrates a specific suppression of COX-2 as compared to COX-1, further supporting the earlier findings. Altogether, the findings could provide an opportunity for these compounds to be developed as novel lead molecules for rational alternatives of NSAIDS.

Keywords

Thiophene-thiadiazolyl Schiff base Catalysis Anti-inflammatory activity NSAIDs COX-1 COX-2
Mishra, G., Dwivedi, P. K., Verma, N., Srivastava, S., Singh, A. K., & Chaturvedi, D. (2023). Cu(II) and Fe(III) Catalyzed Synthesis of Novel Thiophene Hybridized Thiadiazolyl Schiff Bases (TTS) as COX-2 Selective Inhibitor. Asian Journal of Chemistry, 35(6), 1518–1524. https://doi.org/10.14233/ajchem.2023.27745
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