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Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024

Copyright (c) 2024 DIMPLE PIRGAL, SS Karki, S Kumar, Metikurki

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Synthesis, In silico Study and Cytotoxicity Evaluation of Some Newly Synthesized Stilbene Derivatives

https://doi.org/10.14233/ajchem.2024.31942
Dimple Pirgal
Department of Pharmaceutical Chemistry, KLE College of Pharmacy, 2nd Block, Rajajinagar, Bengaluru-560010, India; Dr. Prabhakar B. Kore Basic Science Research Centre, Off-Campus, KLE College of Pharmacy (A Constituent Unit of KLE Academy of Higher Education and Research, Belagavi) Bengaluru-560010, India
https://orcid.org/0000-0001-7565-674X
Subhas S. Karki
Department of Pharmaceutical Chemistry, KLE College of Pharmacy, 2nd Block, Rajajinagar, Bengaluru-560010, India; Dr. Prabhakar B. Kore Basic Science Research Centre, Off-Campus, KLE College of Pharmacy (A Constituent Unit of KLE Academy of Higher Education and Research, Belagavi) Bengaluru-560010, India
https://orcid.org/0000-0002-5599-3594
Sujeet Kumar
Department of Pharmaceutical Chemistry, KLE College of Pharmacy, 2nd Block, Rajajinagar, Bengaluru-560010, India; Department of Pharmaceutical Chemistry, NITTE College of Pharmaceutical Sciences, Govindapura, Yelahanka, Bengaluru-560064, India
https://orcid.org/0000-0002-0833-158X
Basavraj Metikurki
Department of Pharmaceutical Chemistry, NITTE College of Pharmaceutical Sciences, Govindapura, Yelahanka, Bengaluru-560064, India
https://orcid.org/0000-0002-5112-2468

Corresponding Author(s) : Dimple Pirgal

dimplepirgal@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024

Abstract

A series of 12 stilbene derivatives (23-34) were synthesized by reacting benzyl-triphenylphosphonium chlorides (9-14) and hydrochloride salt of 3,5-disubstituted-4-hydroxybenzaldehydes (21-22). The synthesized molecules were tested against the human breast cancer cell line MCF7 by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in 10% Dulbecco’s modified Eagle Medium (DMEM). Compound 23 exhibited significant cytotoxicity, with 1.11% viability at a concentration of 200 µM, compared to the reference standard resveratrol (15.14%) and 5-fluorouracil (51.86%). All the synthesized derivatives demonstrated equipotency to 5-fluorouracil (5-FU) at all the tested concentrations. The docking study was conducted on the tyrosine-protein kinase/Janus Kinase 2(JAK2) receptor using Autodock Vina. The results of the docking study suggest that, with the exception of compounds 29 (-6.7 kcal/mol) and 32 (-7.1 kcal/mol), most of the synthesized derivatives have exhibited glide scores greater than the standard resveratrol (-7.8 kcal/mol). This implies that these compounds 23-34 have a strong binding affinity to the JAK2 receptor, which is relevant in the context of cancer research, as JAK2 is associated with various signaling pathways involved in cell proliferation and survival.

Keywords

Resveratrol Stilbene MCF7 JAK2 MTT
Pirgal, D., Karki, S. S., Kumar, S., & Metikurki, B. (2024). Synthesis, In silico Study and Cytotoxicity Evaluation of Some Newly Synthesized Stilbene Derivatives. Asian Journal of Chemistry, 36(8), 1881–1888. https://doi.org/10.14233/ajchem.2024.31942
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