Isfahan University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! On (X network) By
Synthesis, Cytotoxic Effect Assessment and Molecular Docking Studies of Disubstituted Thiadiazole Including Oxadiazole As Hybrid Component Publisher



Hassanzadeh F1 ; Jafari E1 ; Zarei S1 ; Sadeghialiabadi H1
Authors
Show Affiliations
Authors Affiliations
  1. 1. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran

Source: Hacettepe University Journal of the Faculty of Pharmacy Published:2022


Abstract

Cancer is the second leading cause of death in the world. Due to toxicity and resistance to common therapies, the attempt to develop new anticancer agents has become a major challenge. Oxadiazole and thiadiazole are of interest building blocks used in drug design. Hybrids of thiadiazole-oxadiazole have been synthesized with significant cytotoxic effects. Considering importance of mentioned scaffolds some of the thiadiazole-oxadiazole derivatives were synthesized by three steps in this study. Firstly, thiol function of 2-amino-5-mercapto-1, 3, 4-thiadiazole was alkylated by benzyl chloride derivatives to give compounds (1a-c). The reaction of chloroacetyl chloride with amine group of compounds (1a–c) terminates to amide derivatives (2a-c). Definitive products were produced by treatment of corresponding amide derivatives with 5-(4-chlorophenyl)-1, 3, 4-oxadiazole-2-thiol. Synthesized compounds were evaluated by MTT assay against three cell lines. The final molecules were docked in the active sites of the epidermal growth factor receptor tyrosine kinase to assay the possible interactions. Final products showed range of cytotoxic activity of moderate to good against tested cell lines. Compound (3a) demonstrated a higher cytotoxic activity against MCF-7 (IC50: 26 µM) and Lncap (IC50: 37 µM) cell lines in comparison with other compounds. The highest docking score was-10.55 kcal/mol for compound 3a. © 2022, Hacettepe University, Faculty of Pharmacy. All rights reserved.
Related Docs
View other Related Docs
1. Synthesis, Biological and Docking Studies of Thiadiazole Amide Derivatives Containing Anthranilic Acid, Journal of Sciences, Islamic Republic of Iran (2023)
2. 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)
3. Synthesis, Cytotoxic Evaluation, and Molecular Docking Studies of Some New 1, 3, 4-Oxadiazole-Based Compounds, Research in Pharmaceutical Sciences (2020)
4. Synthesis and Cytotoxic Evaluation of Some Quinazolinone- 5-(4-Chlorophenyl) 1, 3, 4-Oxadiazole Conjugates, Research in Pharmaceutical Sciences (2019)
5. Synthesis and Antimicrobial Evaluation of Some 2,5 Disubstituted 1,3,4-Oxadiazole Derivatives, Research in Pharmaceutical Sciences (2017)
6. Synthesis and Evaluation of Thiadiazole-Based Antileishmanial Agents, Journal of Reports in Pharmaceutical Sciences (2020)
7. Quinazolinone-Based Hybrids With Diverse Biological Activities: A Mini-Review, Journal of Research in Medical Sciences (2022)
8. Docking and Qsar Studies of Some Quinazolinone Derivatives As Possible Inhibitors of Thyrosine Kinase, Turkish Computational and Theoretical Chemistry (2022)
Experts (# of related papers)
View all Related Experts
Farshid Hassanzadeh (20)
Ghadamali Khodarahmi (16)
Other Related Docs
9. Pyrimido[4,5-B]Indole Derivatives Bearing 1,2,4-Oxadiazole Moiety As Mdm2 Inhibitor Candidates in Cancer Treatment, Future Medicinal Chemistry (2023)
10. 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)
11. Novel Catechol Derivatives of Arylimidamides As Antileishmanial Agents, Chemistry and Biodiversity (2018)
12. Quantum Mechanical/Molecular Mechanical and Docking Study of the Novel Analogues Based on Hybridization of Common Pharmacophores As Potential Anti-Breast Cancer Agents, Research in Pharmaceutical Sciences (2017)
13. Synthesis, Characterization, Cytotoxic Screening, and Density Functional Theory Studies of New Derivatives of Quinazolin-4(3H)-One Schiff Bases, Research in Pharmaceutical Sciences (2017)
14. Synthesis, and Molecular Docking Studies of Novel 1,2,3-Triazoles-Linked Pyrazole Carboxamides As Significant Anti-Microbial and Anti-Cancer Agents, Results in Chemistry (2024)
15. Design, Synthesis, and Cytotoxicity Evaluation of Novel Indole-Acylhydrazone Derivatives of 4-Pyridinone As Potential Histone Deacetylase-2 Inhibitors, Research in Pharmaceutical Sciences (2022)
16. Anti-Cancer, Anti-Oxidant and Molecular Docking Studies of Thiosemicarbazone Indole-Based Derivatives, Research on Chemical Intermediates (2019)
17. Quinazolinone and Quinazoline Derivatives: Recent Structures With Potent Antimicrobial and Cytotoxic Activities, Research in Pharmaceutical Sciences (2016)
18. Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study, Chemistry and Biodiversity (2019)
19. Exploring the Interaction Between Epidermal Growth Factor Receptor Tyrosine Kinase and Some of the Synthesized Inhibitors Using Combination of In-Silico and In-Vitro Cytotoxicity Methods, Research in Pharmaceutical Sciences (2018)
20. Some Novel Hybrid Quinazoline-Based Heterocycles As Potent Cytotoxic Agents, Research in Pharmaceutical Sciences (2022)
21. Synthesis and Cytotoxic Evaluation of Two Novel Anthraquinone Derivatives, Farmaco (2004)
22. Dihydropyrimidine Derivatives As Mdm2 Inhibitors, Chemical Biology and Drug Design (2024)
23. Monastrol Derivatives: In Silico and in Vitro Cytotoxicity Assessments, Research in Pharmaceutical Sciences (2020)
24. 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)
25. Design of Novel Potential Aromatase Inhibitors Via Hybrid Pharmacophore Approach: Docking Improvement Using the Qm/Mm Method, RSC Advances (2015)
26. Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation, Chemistry and Biodiversity (2017)
27. Synthesis and Cytotoxic Evaluation of Novel Quinozalinone Derivatives With Substituted Benzimidazole in Position 3, Research in Pharmaceutical Sciences (2019)
28. Design, Synthesis and Biological Activity of Hybrid Antifungals Derived From Fluconazole and Mebendazole, European Journal of Medicinal Chemistry (2023)
29. 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)
30. Synthesis and Cytotoxic Evaluation of Some New 4(3H)-Quinazolinones on Hela Cell Line, Research in Pharmaceutical Sciences (2012)
31. The Art of Design in Azlactone-Benzoxazinone Chemistry, Docking Studies and in Vitro Cytotoxicity Evaluation, Australian Journal of Chemistry (2022)
32. Synthesis and Cytotoxic Evaluation of Some Novel Diarylamide Possessing Quinoxalinedione Based on Sorafenib, Research in Pharmaceutical Sciences (2018)
33. 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)
34. Synthesis of Some Benzothiazole Derivatives Based on 3-Hydroxypyridine-4-One and Benzaldehyde and Evaluation of Their Β-Amyloid Aggregation Inhibition Using Both Experimental Methods and Molecular Dynamic Simulation, Chemistry and Biodiversity (2023)
35. Synthesis, Characterization, Molecular Docking, Antimalarial, and Antiproliferative Activities of Benzyloxy-4-Oxopyridin Benzoate Derivatives, Research in Pharmaceutical Sciences (2022)
36. 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)
37. Benzothiazolopyridine Compounds: Facial Synthesis, Characterization, and Molecular Docking Study on Estrogen and Progesterone Receptors, Journal of Molecular Structure (2021)
38. Synthesis and Biological Evaluation of Tetrahydropyrimidine and Dihydropyridine Derivatives Against Leishmania Major, Acta Parasitologica (2022)
39. Synthesis, Biological Assessment, and Computational Investigations of Nifedipine and Monastrol Analogues As Anti-Leishmanial Major and Anti-Microbial Agents, Molecular Diversity (2023)
40. Investigation of Biological Effects of New Tetrazole Compounds on Cancer Cell Lines (Hela, Mcf-7) and Common Microorganisms (Staphylococcus Aureus, Escherichia Coli, Candida Albicans), Journal of Isfahan Medical School (2023)
41. Synthesis and Cytotoxic Evaluation of Some Derivatives of Triazole-Quinazolinone Hybrids, Research in Pharmaceutical Sciences (2019)
42. Synthesis and Cytotoxicity Evaluation of Some New 6-Nitro Derivatives of Thiazole-Containing 4-(3H)-Quinazolinone, Research in Pharmaceutical Sciences (2016)
43. Synthesis and Antifungal Activity Evaluation of a Fluconazole Analog Derived From Dithiocarbamate, Journal of Mazandaran University of Medical Sciences (2024)
44. Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Novel Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties As Potential Cytotoxic and Antimicrobial Agents, Iranian Journal of Basic Medical Sciences (2017)
45. Synthesis and Primary Cytotoxic Screening of Some 3-Sulfonamide Substituted Benzamido-Benzimidazolones, Iranian Journal of Pharmaceutical Research (2005)