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

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Feb 28, 2023
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Feb 27, 2023

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

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
yrp@sau.ac.in
Faculty of Life Science and Biotechnology, South Asian University, Akbar Bhawan, Chanakyapuri, New Delhi-110021, India
Paras Nath Yadav
pnyadav219@gmail.com
Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu 44618, Nepal

Corresponding Author(s) : Yuba Raj Pokharel

yrp@sau.ac.in

Corresponding Author(s) : Paras Nath Yadav

pnyadav219@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 3 (2023): Vol 35 Issue 3 page 605-616

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
ChaudharyU., GurungV., Tariq PachakhanS., Adhikari SubinJ., Raj PokharelY., & Nath YadavP. (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. Retrieved from https://asianpubs.org/index.php/ajchem/article/view/27758
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