Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):

Share this content! On (X network) By

Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study Publisher Pubmed

Bakherad Z¹ ; Safavi M² ; Fassihi A¹ ; Sadeghialiabadi H¹ ; Bakherad M³ ; Rastegar H⁴ ; Saeedi M^{5, 6} ; Ghasemi JB⁷ ; Saghaie L¹ ; Mahdavi M⁸

Show Affiliations

1. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, 81746-73461, Iran
2. Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, 33535-111, Iran
3. School of Chemistry, Shahrood University of Technology, Shahrood, 3619995161, Iran
4. Food and Drug Control Laboratories, Food and Drug Laboratory Research Center, MOE and ME, Tehran, 1113615911, Iran
5. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 14176, Iran
6. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, 14176, Iran
7. Drug Design in Silico Lab, Chemistry Faculty, School of Sciences, University of Tehran, Teheran, 1417614418, Iran
8. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Research Institute, Tehran University of Medical Sciences, Tehran, 1417653761, Iran

Source: Chemistry and Biodiversity Published:2019

Abstract

In this work, two novel series of indole-thiosemicarbazone derivatives were designed, synthesized, and evaluated for their cytotoxic activity against MCF-7, A-549, and Hep-G2 cell lines in comparison to etoposide and colchicine as the reference drugs. Generally, the synthesized compounds showed better cytotoxicity towards A-549 and Hep-G2 than MCF-7. Among them, (2E)-2-{[2-(4-chlorophenyl)-1H-indol-3-yl]methylidene}-N-(4-methoxyphenyl)hydrazinecarbothioamide (8l) was found to be the most potent compound against A-549 and Hep-G2, at least three times more potent than etoposide. The morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that compound 8l induced apoptosis in A-549 cells. Moreover, molecular docking methodology was exploited to elucidate the details of molecular interactions of the studied compounds with putative targets. © 2019 Wiley-VHCA AG, Zurich, Switzerland

Related Docs

View other Related Docs

1. Anti-Cancer, Anti-Oxidant and Molecular Docking Studies of Thiosemicarbazone Indole-Based Derivatives, Research on Chemical Intermediates (2019)

2. Design, Synthesis, and Cytotoxicity Evaluation of Novel Indole-Acylhydrazone Derivatives of 4-Pyridinone As Potential Histone Deacetylase-2 Inhibitors, Research in Pharmaceutical Sciences (2022)

3. Preparation of Some Novel Imidazopyridine Derivatives of Indole As Anticancer Agents: One-Pot Multicomponent Synthesis, Biological Evaluation and Docking Studies, Research on Chemical Intermediates (2019)

4. In Silico and in Vitro Studies of Thiosemicarbazone-Indole Hybrid Compounds As Potent Α-Glycosidase Inhibitors, Computational Biology and Chemistry (2022)

5. Novel Catechol Derivatives of Arylimidamides As Antileishmanial Agents, Chemistry and Biodiversity (2018)

6. Novel 9-(Alkylthio)-Acenaphtho[1,2-E]-1,2,4-Triazine Derivatives: Synthesis, Cytotoxic Activity and Molecular Docking Studies on B-Cell Lymphoma 2 (Bcl-2), DARU, Journal of Pharmaceutical Sciences (2014)

7. Synthesis, Characterization, Cytotoxic Screening, and Density Functional Theory Studies of New Derivatives of Quinazolin-4(3H)-One Schiff Bases, Research in Pharmaceutical Sciences (2017)

8. Novel Tocopherol Succinate-Polyoxomolybdate Bioconjugate As Potential Anti-Cancer Agent, Journal of Inorganic and Organometallic Polymers and Materials (2021)

Experts (# of related papers)

View all Related Experts

Farshid Hassanzadeh (13)

Mahboubeh Rostami (9)

Other Related Docs

9. Synthesis and Antimicrobial Evaluation of Some 2,5 Disubstituted 1,3,4-Oxadiazole Derivatives, Research in Pharmaceutical Sciences (2017)

10. Synthesis of Novel Conjugated Benzofuran-Triazine Derivatives: Antimicrobial and In-Silico Molecular Docking Studies, Heliyon (2023)

11. Synthesis and Cytotoxic Evaluation of Some New 3-(2-(2-Phenylthiazol-4-Yl) Ethyl)-Quinazolin-4(3H) One Derivatives With Potential Anticancer Effects, Research in Pharmaceutical Sciences (2017)

12. Some Novel Hybrid Quinazoline-Based Heterocycles As Potent Cytotoxic Agents, Research in Pharmaceutical Sciences (2022)

13. Qsar Study of Some 5-Methyl/Trifluoromethoxy-1H-Indole-2,3-Dione-3- Thiosemicarbazone Derivatives As Anti-Tubercular Agents, Research in Pharmaceutical Sciences (2009)

14. Monastrol Derivatives: In Silico and in Vitro Cytotoxicity Assessments, Research in Pharmaceutical Sciences (2020)

15. Synthesis and Cytotoxic Evaluation of Some Novel 3-[2-(2-Phenyl-Thiazol-4-Yl)-Ethyl] -3H-Pyrido [2,3-D]Pyrimidin-4-One Derivatives, Research in Pharmaceutical Sciences (2021)

16. Synthesis and Cytotoxic Activity Evaluation of Some New 1, 3, 4-Oxadiazole, 1, 3, 4-Thiadiazole and 1, 2, 4- Triazole Derivatives Attached to Phthalimide, Research in Pharmaceutical Sciences (2021)

17. Design, Synthesis, in Silico Studies, and Antiproliferative Evaluations of Novel Indolin-2-One Derivatives Containing 3-Hydroxy-4-Pyridinone Fragment, Bioorganic and Medicinal Chemistry Letters (2022)

18. Synthesis, Biological Evaluation and Molecular Docking Study of Dihydropyrimidine Derivatives As Potential Anticancer Agents, Journal of Heterocyclic Chemistry (2020)

19. The Art of Design in Azlactone-Benzoxazinone Chemistry, Docking Studies and in Vitro Cytotoxicity Evaluation, Australian Journal of Chemistry (2022)

20. Synthesis and Cytotoxic Evaluation of Some Novel Diarylamide Possessing Quinoxalinedione Based on Sorafenib, Research in Pharmaceutical Sciences (2018)

21. Pyrimido[4,5-B]Indole Derivatives Bearing 1,2,4-Oxadiazole Moiety As Mdm2 Inhibitor Candidates in Cancer Treatment, Future Medicinal Chemistry (2023)

22. Biological Evaluation, Docking and Molecular Dynamic Simulation of Some Novel Diaryl Urea Derivatives Bearing Quinoxalindione Moiety, Research in Pharmaceutical Sciences (2017)

23. Synthesis, Qsar Modeling, and Molecular Docking Studies of 1,2,3-Triazole-Pyrazole Hybrids As Significant Anti-Cancer and Anti-Microbial Agents, Journal of Molecular Structure (2025)

24. In Silico Screening for Novel Tyrosine Kinase Inhibitors With Oxindole Scaffold As Anti-Cancer Agents: Design, Qsar Analysis, Molecular Docking and Admet Studies, Journal of Computational Biophysics and Chemistry (2022)

25. Synthesis, Characterization, Molecular Docking, Antimalarial, and Antiproliferative Activities of Benzyloxy-4-Oxopyridin Benzoate Derivatives, Research in Pharmaceutical Sciences (2022)

26. Synthesis, Biological Assessment, and Computational Investigations of Nifedipine and Monastrol Analogues As Anti-Leishmanial Major and Anti-Microbial Agents, Molecular Diversity (2023)

27. Synthesis, Biological and Docking Studies of Thiadiazole Amide Derivatives Containing Anthranilic Acid, Journal of Sciences, Islamic Republic of Iran (2023)

28. Synthesis and Evaluation of Thiadiazole-Based Antileishmanial Agents, Journal of Reports in Pharmaceutical Sciences (2020)

29. Synthesis, Cytotoxic Evaluation, and Molecular Docking Studies of Some New 1, 3, 4-Oxadiazole-Based Compounds, Research in Pharmaceutical Sciences (2020)

30. Synthesis, Cytotoxic Effect Assessment and Molecular Docking Studies of Disubstituted Thiadiazole Including Oxadiazole As Hybrid Component, Hacettepe University Journal of the Faculty of Pharmacy (2022)

Style	Citing Format
MLA	Bakherad Z, et al.. "Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study." Chemistry and Biodiversity, vol. 16, no. 4, 2019, pp. -.
APA	Bakherad Z, Safavi M, Fassihi A, Sadeghialiabadi H, Bakherad M, Rastegar H, Saeedi M, Ghasemi JB, Saghaie L, Mahdavi M (2019). Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study. Chemistry and Biodiversity, 16(4), -.
Chicago	Bakherad Z, Safavi M, Fassihi A, Sadeghialiabadi H, Bakherad M, Rastegar H, Saeedi M, Ghasemi JB, Saghaie L, Mahdavi M. "Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study." Chemistry and Biodiversity 16, no. 4 (2019): -.
Harvard	Bakherad Z et al. (2019) 'Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study', Chemistry and Biodiversity, 16(4), pp. -.
Vancouver	Bakherad Z, Safavi M, Fassihi A, Sadeghialiabadi H, Bakherad M, Rastegar H, et al.. Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study. Chemistry and Biodiversity. 2019;16(4):-.
BibTex	@article{ author = {Bakherad Z and Safavi M and Fassihi A and Sadeghialiabadi H and Bakherad M and Rastegar H and Saeedi M and Ghasemi JB and Saghaie L and Mahdavi M}, title = {Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study}, journal = {Chemistry and Biodiversity}, volume = {16}, number = {4}, pages = {-}, year = {2019} }
RIS	TY - JOUR AU - Bakherad Z AU - Safavi M AU - Fassihi A AU - Sadeghialiabadi H AU - Bakherad M AU - Rastegar H AU - Saeedi M AU - Ghasemi JB AU - Saghaie L AU - Mahdavi M TI - Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study JO - Chemistry and Biodiversity VL - 16 IS - 4 SP - EP - PY - 2019 ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract