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Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023

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Evaluation of Anticancer Potential of N(4)-Alkyl Substituted 5-Methoxyisatin Thiosemicarbazones: Synthesis, Characterization and Molecular Docking

https://doi.org/10.14233/ajchem.2023.26967
Upendra Chaudhary
Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu 44618, Nepal
Vijay Gurung
Faculty of Life Science and Biotechnology, South Asian University, Akbar Bhawan, Chanakyapuri, New Delhi-110021, India
Sayed Tariq Pachakhan
Faculty of Life Science and Biotechnology, South Asian University, Akbar Bhawan, Chanakyapuri, New Delhi-110021, India
Jhashanath Adhikari Subin
3 Department of Chemistry, D.A.V. College, Jawalakhel, Lalitpur 44700, Nepal
Yuba Raj Pokharel
Faculty of Life Science and Biotechnology, South Asian University, Akbar Bhawan, Chanakyapuri, New Delhi-110021, India
Paras Nath Yadav
Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu 44618, Nepal

Corresponding Author(s) : Yuba Raj Pokharel

yrp@sau.ac.in

Asian Journal of Chemistry, Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023

Abstract

(Z)-N-ethyl-2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazine-1-carbothioamide (MeOIstEt) and (Z)-2-(5-methoxy-2-oxoindolin-3-ylidene)-N-methylhydrazine-1-carbothioamide (MeOIstMe) were synthesized and subjected to elemental analysis and various characterization techniques viz. IR, 1H NMR, 13C NMR, UV-Vis and HRMS. The synthesized N(4)-alkyl substituted thiosemicarbazones were evaluated for their anticancer activity against various cancer cell lines like breast cancer (MCF-7), skin cancer (A431) and lung cancer (A549). In micromolar concentrations, the synthesized compounds exhibited moderate anticancer activity (IC50, 6.59-36.49 μM). The compound MeOIstEt was found to be more effective than MeOIstMe against A549 and MCF-7 cell lines, whereas compound MeOIstMe was found to be more potent against A431 cell lines. From flexible receptor molecular docking calculations in a hydrated environment, one of the compounds showed better binding affinity than one FDA approved drug. The insights from computational studies have strengthened the experimental findings and vice-versa. This work demonstrates the role of multiple approaches in finding better drug candidate with efficient anti-cancer properties.

Keywords

Anticancer activity Breast cancer 5-Methoxyisatin Molecular docking Thiosemicarbazones
Chaudhary, U., Gurung, V., Tariq Pachakhan, S., Adhikari Subin, J., Raj Pokharel, Y., & Nath Yadav, P. (2023). Evaluation of Anticancer Potential of N(4)-Alkyl Substituted 5-Methoxyisatin Thiosemicarbazones: Synthesis, Characterization and Molecular Docking. Asian Journal of Chemistry, 35(3), 605–616. https://doi.org/10.14233/ajchem.2023.26967
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