An Improved Synthesis of Key Intermediate to the Formation of selected Indolin-2-ones Derivatives Incorporating Ultrasound and Deep Eutectic Solvent (DES) Blend of Techniques, for some Biological Activities and Molecular Docking Studies

Md Bakht; Mohd Imran; Abida Khan; Md. Alam; Anouar Hassane; Mohammed Alshammari; Noushin Ajmal; Archana Vimal; Awanish Kumar; Yassine Riadi

doi:10.3390/ecsoc-23-06592

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An Improved Synthesis of Key Intermediate to the Formation of selected Indolin-2-ones Derivatives Incorporating Ultrasound and Deep Eutectic Solvent (DES) Blend of Techniques, for some Biological Activities and Molecular Docking Studies

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¹ Department of Chemistry, College Science and Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box- 173, Al-Kharj 11942, Saudi Arabia
² Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Northern Border University, Rafha 91911, P.O. Box 840 Kingdom of Saudi Arabia
³ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Northern Border University, Rafha 91911, P.O. Box 840 Kingdom of Saudi Arabia.
⁴ Department of Chemistry, College Science and Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box- 173, Al-Kharj 11942, Saudi Arabia.
⁵ Department of Basic Sciences and Humanities, Pratap University, Jaipur, 303104, Rajasthan, India
⁶ Department of Biotechnology, National Institute of Technology Raipur C. G., INDIA.
⁷ Department of Biotechnology, National Institute of Technology Raipur C. G., INDIA
⁸ Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, P.O. Box- 173, Al-Kharj 11942, Saudi Arabia

Published: 14 November 2019 by MDPI in The 23rd International Electronic Conference on Synthetic Organic Chemistry session Bioorganic, Medicinal and Natural Products Chemistry

https://doi.org/10.3390/ecsoc-23-06592

Abstract:

We have developed a new idea to synthesize key intermediate molecule by utilizing deep eutectic solvent (DES) and ultrasound in a multistep reaction to ensure process cost-effective. Key intermediate (3) and final compounds (4a-n) were synthesized in a higher yield of 95% and 80-88% respectively.Further, final compounds (4a-n) were assessed for their anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation.The compounds 4f, 4g, 4j, 4l, and 4m showed good anti-inflammatory activity, while 4f, 4i, and 4n exhibited very good analgesic activity ascompared to the standard drug. The ulcerogenicity of selected compounds was far less than the indomethacin. The ligands had also shown a good docking score (4f = -6.859 and 4 n= -7.077) as compared to control indomethacin (-6.109).State-of-art DFT theory was used to validate the lipid peroxidation mechanism of the active compoundswhich was in good agreement with the variations of BDEs and IP of the tested compounds.

Keywords: Thiazole-indole; DES; Ultrasound; anti-inflammatory; analgesic; ulcerogenic; lipid peroxidation; molecular docking; DFT theory

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