Design, Synthesis, in Silico Studies, and Antiproliferative Evaluations of Novel Indolin-2-One Derivatives Containing 3-Hydroxy-4-Pyridinone Fragment

Science Communicator Platform

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

Share this content! On (X network) By

Design, Synthesis, in Silico Studies, and Antiproliferative Evaluations of Novel Indolin-2-One Derivatives Containing 3-Hydroxy-4-Pyridinone Fragment Publisher Pubmed

Shirvani P¹ ; Fayyazi N^{1, 2} ; Van Belle S³ ; Debyser Z³ ; Christ F³ ; Saghaie L¹ ; Fassihi A¹

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Science, Isfahan University of Medical Science, Hezar Jerib, 817416-73461, Isfahan, Iran
2. Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
3. Department of Pharmacological and Pharmaceutical Sciences, Laboratory of Molecular Virology and Gene Therapy, KU Leuven, Belgium

Source: Bioorganic and Medicinal Chemistry Letters Published:2022

Abstract

Keeping in view the pharmacological properties of indolinones as promising scaffold as kinase inhibitors, herein, a novel series of 3-hydrazonoindolin-2-one derivatives bearing 3-hydroxy-4-pyridinone moiety were synthesized, studied by molecular docking, and fully characterized by spectroscopic techniques. All the prepared compounds were evaluated for their cytotoxicity attributes against a panel of tumor cell lines, including non-small cell lung cancer (A549), breast carcinoma (MCF-7), acute myeloid leukemia (AML), and chronic myeloid leukemia (CML). They displayed moderate to promising antiproliferative effects toward A549 and MCF-7 cells but remarkable results against AML and CML. Especially, compound 10k was found to be more potent against AML (EC50 = 0.69 μM) compare to the other halogen-substituted derivatives. FMS-like tyrosine kinase 3 (FLT3) is known to be expressed in AML cancer cells. The molecular docking studies demonstrated that our prepared compounds were potentially bound to AML active site through essential H-bond and other vital interactions with critical binding residues. © 2022

Related Docs

View other Related Docs

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

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

4. 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)

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

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

7. Design of Novel Potential Aromatase Inhibitors Via Hybrid Pharmacophore Approach: Docking Improvement Using the Qm/Mm Method, RSC Advances (2015)

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

Experts (# of related papers)

View all Related Experts

Farshid Hassanzadeh (23)

Ghadamali Khodarahmi (16)

Other Related Docs

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

10. The Neutrophil-To-Lymphocyte Ratio As a New Prognostic Factor in Cancers: A Narrative Review, Frontiers in Oncology (2023)

11. 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)

12. Persicoimidate Isolated From Allium Ampeloprasum Subsp. Persicum With Apoptotic Effects Against Breast Cancer Cell Lines, Iranian Journal of Pharmaceutical Sciences (2020)

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. Multifunctional Plant Virus Nanoparticles for Targeting Breast Cancer Tumors, Vaccines (2022)

15. Apoptosis-Inducing Effect of Spiroaminopyrimidine Analogue in Nb4 Leukemia Cells Via Down-Regulation of Birc5 Expression, Experimental Oncology (2019)

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

17. Exploiting New Strategies in Combating Head and Neck Carcinoma: A Comprehensive Review on Phytochemical Approaches Passing Through Pi3k/Akt/Mtor Signaling Pathway, Phytotherapy Research (2024)

18. New 3-Hydroxypyridine-4-One Analogues: Their Synthesis, Antimicrobial Evaluation, Molecular Docking, and in Silico Adme Prediction, Medicinal Chemistry (2024)

19. Therapeutic Opportunities in Breast Cancer by Targeting Macrophage Migration Inhibitory Factor As a Pleiotropic Cytokine, Breast Cancer: Basic and Clinical Research (2024)

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

21. Synthesis, Anti-Hiv-1 and Antiproliferative Evaluation of Novel 4-Nitroimidazole Derivatives Combined With 5-Hydroxy-4-Pyridinone Moiety, Journal of Molecular Structure (2020)

22. Synthesis and Characterization of Some Novel Diaryl Urea Derivatives Bearing Quinoxalindione Moiety, Research in Pharmaceutical Sciences (2018)

23. Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study, Chemistry and Biodiversity (2019)

24. Hydroxypyridinone Derivatives: Synthesis and Cytotoxic Evaluation, Journal of Reports in Pharmaceutical Sciences (2013)

25. 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)

26. 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)

27. Unusual Ingenoids From Euphorbia Erythradenia Bioss. With Pro-Apoptotic Effects, Fitoterapia (2013)

28. Synthesis and Cytotoxic Evaluation of Two Novel Anthraquinone Derivatives, Farmaco (2004)

29. Dihydropyrimidine Derivatives As Mdm2 Inhibitors, Chemical Biology and Drug Design (2024)

30. Two New Dammarane Triterpenes Isolated From Cleome Khorassanica Bunge & Bien With Cytotoxicity Against Du-145 and Lncap Prostate Cancer Cell Lines, Journal of Asian Natural Products Research (2020)

31. Synthesis and Cytotoxic Evaluation of Some Quinazolinone- 5-(4-Chlorophenyl) 1, 3, 4-Oxadiazole Conjugates, Research in Pharmaceutical Sciences (2019)

32. An Integrated in Silico Screening Strategy for Identifying Promising Disruptors of P53-Mdm2 Interaction, Computational Biology and Chemistry (2019)

33. Formononetin and Dihydroartemisinin Act Synergistically to Induce Apoptosis in Human Acute Myeloid Leukemia Cell Lines, Cell Journal (2024)

34. Potential Role of Thymoquinone to Treat Gastrointestinal Cancers: Insights Into Its Molecular Mechanisms, Naunyn-Schmiedeberg's Archives of Pharmacology (2025)

35. Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation, Chemistry and Biodiversity (2017)

36. Quercetin Modulates Signal Transductions and Targets Non-Coding Rnas Against Cancer Development, Cellular Signalling (2023)

37. Melatonin for Gastric Cancer Treatment: Where Do We Stand?, Naunyn-Schmiedeberg's Archives of Pharmacology (2025)

38. 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)

39. Biological Effects of Letrozole-Loaded Lipid Nanocapsules on Mcf-7 Cell Line, Journal of Isfahan Medical School (2013)

40. Design, Synthesis, Bioactivity Analyses, and Molecular Docking Study of Triazine-Tyrosine Based Derivatives As Drugs Like Fingolimod for Treatment of Multiple Sclerosis, Polycyclic Aromatic Compounds (2024)

41. Synergistic Antitumor Effect of Nvp-Bez235 and Cape on Mda-Mb-231 Breast Cancer Cells, Biomedicine and Pharmacotherapy (2017)

42. Synthesis and Cytotoxic Evaluation of Some New 4(3H)-Quinazolinones on Hela Cell Line, Research in Pharmaceutical Sciences (2012)

43. Molecular Modelling Study on Pyrrolo[2,3-B]Pyridine Derivatives As C-Met Kinase Inhibitors: A Combined Approach Using Molecular Docking, 3D-Qsar Modelling and Molecular Dynamics Simulation, Molecular Simulation (2020)

44. Design, Synthesis, and Anticancer Activity of Phosphonic Acid Diphosphate Derivative of Adenine-Containing Butenolide and Its Water-Soluble Derivatives of Paclitaxel With High Antitumor Activity, Bioorganic and Medicinal Chemistry (2003)

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

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

47. Phytochemical Analysis of Daphne Pontica L. Stems With Their Pro-Apoptotic Properties Against Du-145 and Lncap Prostate Cancer Cells, DARU, Journal of Pharmaceutical Sciences (2022)

48. 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)

49. Quinazolinone-Based Hybrids With Diverse Biological Activities: A Mini-Review, Journal of Research in Medical Sciences (2022)

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

Style	Citing Format
MLA	Shirvani P, et al.. "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, vol. 70, no. , 2022, pp. -.
APA	Shirvani P, Fayyazi N, Van Belle S, Debyser Z, Christ F, Saghaie L, Fassihi A (2022). 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, 70(), -.
Chicago	Shirvani P, Fayyazi N, Van Belle S, Debyser Z, Christ F, Saghaie L, Fassihi A. "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 70, no. (2022): -.
Harvard	Shirvani P et al. (2022) '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, 70(), pp. -.
Vancouver	Shirvani P, Fayyazi N, Van Belle S, Debyser Z, Christ F, Saghaie L, et al.. 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;70():-.
BibTex	@article{ author = {Shirvani P and Fayyazi N and Van Belle S and Debyser Z and Christ F and Saghaie L and Fassihi A}, title = {Design, Synthesis, in Silico Studies, and Antiproliferative Evaluations of Novel Indolin-2-One Derivatives Containing 3-Hydroxy-4-Pyridinone Fragment}, journal = {Bioorganic and Medicinal Chemistry Letters}, volume = {70}, number = {}, pages = {-}, year = {2022} }
RIS	TY - JOUR AU - Shirvani P AU - Fayyazi N AU - Van Belle S AU - Debyser Z AU - Christ F AU - Saghaie L AU - Fassihi A TI - Design, Synthesis, in Silico Studies, and Antiproliferative Evaluations of Novel Indolin-2-One Derivatives Containing 3-Hydroxy-4-Pyridinone Fragment JO - Bioorganic and Medicinal Chemistry Letters VL - 70 IS - SP - EP - PY - 2022 ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract