Isfahan University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! On (X network) By
Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation Publisher Pubmed



Asadi P1 ; Khodarahmi G1 ; Jahaniannajafabadi A2 ; Saghaie L1 ; Hassanzadeh F1
Authors
Show Affiliations
Authors Affiliations
  1. 1. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, 81746-73461, Iran
  2. 2. Department of Pharmaceutical Biotechnology, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, 81746-73461, Iran

Source: Chemistry and Biodiversity Published:2017


Abstract

Cytotoxic and antimicrobial agents structurally based on quinazolinone, benzofuran and imidazole pharmacophores, have been designed and synthesized. Spectral (IR, 1H-NMR) and elemental analysis data established the structures of these novel 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride hybrid derivatives. All the synthesized compounds were evaluated for in vitro cytotoxicity and antimicrobial activities. Cytotoxic evaluation using MTT assay revealed that compounds 12c, 12g and 12i exhibited significant cytotoxicity with IC50 values 1, 1, and 0.57 μm on this cell line, respectively. Biological activity of the synthesized compounds as antibacterial agent were also evaluated against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-positive (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungi (Candida albicans) strains. All compounds 12a – 12i showed slightly higher activity against Gram-positive bacteria than the Gram-negative one. Among the nine new compounds screened, 3-[1-(5-bromo-1-benzofuran-2-yl)-2-(6-chloro-4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride (12e) has pronounced higher antimicrobial activity against all tested strains. These results demonstrated potential importance of molecular hybridization in the development of new lead molecules with major cytotoxicity and antimicrobial activity. © 2017 Wiley-VHCA AG, Zurich, Switzerland
Related Docs
View other Related Docs
1. 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)
2. Synthesis and Cytotoxicity Evaluation of Some New 6-Nitro Derivatives of Thiazole-Containing 4-(3H)-Quinazolinone, Research in Pharmaceutical Sciences (2016)
3. Synthesis, Spectroscopic Characterization, Antimicrobial Evaluation and Molecular Docking Study of Novel Triazine-Quinazolinone Based Hybrids, Journal of Molecular Structure (2018)
4. Synthesis and Cytotoxic Evaluation of Some New 4(3H)-Quinazolinones on Hela Cell Line, Research in Pharmaceutical Sciences (2012)
5. Synthesis and Cytotoxic Evaluation of Novel Quinozalinone Derivatives With Substituted Benzimidazole in Position 3, Research in Pharmaceutical Sciences (2019)
6. Antibacterial, Antifungal and Cytotoxic Evaluation of Some New 2,3-Disubstituted 4(3H)-Quinazolinone Derivatives, Research in Pharmaceutical Sciences (2012)
7. 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)
8. Synthesis and Cytotoxic Evaluation of Some Derivatives of Triazole-Quinazolinone Hybrids, Research in Pharmaceutical Sciences (2019)
Experts (# of related papers)
View all Related Experts
Farshid Hassanzadeh (29)
Ghadamali Khodarahmi (22)
Other Related Docs
9. Antibacterial, Antifungal and Cytotoxic Evaluation of Some New Quinazolinone Derivatives, Research in Pharmaceutical Sciences (2012)
10. 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)
11. Quinazolinone-Based Hybrids With Diverse Biological Activities: A Mini-Review, Journal of Research in Medical Sciences (2022)
12. 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)
13. Docking Study, Synthesis and Antimicrobial Evaluation of Some Novel 4-Anilinoquinazoline Derivatives, Research in Pharmaceutical Sciences (2017)
14. Synthesis and Cytotoxic Evaluation of Some Quinazolinone- 5-(4-Chlorophenyl) 1, 3, 4-Oxadiazole Conjugates, Research in Pharmaceutical Sciences (2019)
15. Some Novel Hybrid Quinazoline-Based Heterocycles As Potent Cytotoxic Agents, Research in Pharmaceutical Sciences (2022)
16. Quinazolinone and Quinazoline Derivatives: Recent Structures With Potent Antimicrobial and Cytotoxic Activities, Research in Pharmaceutical Sciences (2016)
17. 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)
18. Docking and Qsar Studies of Some Quinazolinone Derivatives As Possible Inhibitors of Thyrosine Kinase, Turkish Computational and Theoretical Chemistry (2022)
19. New 3-Hydroxypyridine-4-One Analogues: Their Synthesis, Antimicrobial Evaluation, Molecular Docking, and in Silico Adme Prediction, Medicinal Chemistry (2024)
20. Synthesis and Antimicrobial Evaluation of Some 2,5 Disubstituted 1,3,4-Oxadiazole Derivatives, Research in Pharmaceutical Sciences (2017)
21. Synthesis, Antimicrobial Evaluation, Molecular Docking, and Adme Studies of Some Novel 3-Hydroxypyridine-4-One Derivatives, ChemistrySelect (2023)
22. Synthesis, Anti-Hiv-1 and Antiproliferative Evaluation of Novel 4-Nitroimidazole Derivatives Combined With 5-Hydroxy-4-Pyridinone Moiety, Journal of Molecular Structure (2020)
23. Design of Novel Potential Aromatase Inhibitors Via Hybrid Pharmacophore Approach: Docking Improvement Using the Qm/Mm Method, RSC Advances (2015)
24. Benzofuran As a Promising Scaffold for the Synthesis of Antimicrobial and Antibreast Cancer Agents: A Review, Journal of Research in Medical Sciences (2015)
25. 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)
26. Synthesis and Antitubercular Activity of Novel 4-Substituted Imidazolyl-2,6-Dimethyl-N3,N5-Bisaryl-1,4-Dihydropyridine-3,5-Dicarboxamides, European Journal of Medicinal Chemistry (2009)
27. Novel N-Α-Amino Acid Spacer-Conjugated Phthalimide–Triazine Derivatives: Synthesis, Antimicrobial and Molecular Docking Studies, Amino Acids (2023)
28. The Art of Design in Azlactone-Benzoxazinone Chemistry, Docking Studies and in Vitro Cytotoxicity Evaluation, Australian Journal of Chemistry (2022)
29. Pyrimido[4,5-B]Indole Derivatives Bearing 1,2,4-Oxadiazole Moiety As Mdm2 Inhibitor Candidates in Cancer Treatment, Future Medicinal Chemistry (2023)
30. Solvent-Free Synthesis, Adme Prediction, and Evaluation of Antibacterial Activity of Novel Sulfonamide Derivatives, Russian Journal of Organic Chemistry (2019)
31. Biological Evaluation, Docking and Molecular Dynamic Simulation of Some Novel Diaryl Urea Derivatives Bearing Quinoxalindione Moiety, Research in Pharmaceutical Sciences (2017)
32. Synthesis, Characterization, Molecular Docking, Antimalarial, and Antiproliferative Activities of Benzyloxy-4-Oxopyridin Benzoate Derivatives, Research in Pharmaceutical Sciences (2022)
33. Synthesis, Antimicrobial Evaluation and Qsar Study of Some 3-Hydroxypyridine-4-One and 3-Hydroxypyran-4-One Derivatives, European Journal of Medicinal Chemistry (2009)
34. 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)
35. New Thiosemicarbazide-1,2,3-Triazole Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, and Biological Evaluation, Journal of Molecular Structure (2019)
36. Synthesis, Biological Assessment, and Computational Investigations of Nifedipine and Monastrol Analogues As Anti-Leishmanial Major and Anti-Microbial Agents, Molecular Diversity (2023)
37. Synthesis of Some New 2,3-Disubstituted-4(3H)Quinazolinone Derivatives, Research in Pharmaceutical Sciences (2012)
38. Synthesis, Biological and Docking Studies of Thiadiazole Amide Derivatives Containing Anthranilic Acid, Journal of Sciences, Islamic Republic of Iran (2023)
39. Synthesis, Cytotoxic Evaluation, and Molecular Docking Studies of Some New 1, 3, 4-Oxadiazole-Based Compounds, Research in Pharmaceutical Sciences (2020)
40. Synthesis and Antifungal Activity Evaluation of a Fluconazole Analog Derived From Dithiocarbamate, Journal of Mazandaran University of Medical Sciences (2024)
41. Cyclic Imide Derivatives: As Promising Scaffold for the Synthesis of Antimicrobial Agents, Journal of Research in Medical Sciences (2018)
42. 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)
43. Synthesis and Primary Cytotoxic Screening of Some 3-Sulfonamide Substituted Benzamido-Benzimidazolones, Iranian Journal of Pharmaceutical Research (2005)
44. 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)
45. Synthesis of Novel Conjugated Benzofuran-Triazine Derivatives: Antimicrobial and In-Silico Molecular Docking Studies, Heliyon (2023)
46. 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)
47. Antimicrobial and Cytotoxic Naphthoquinones From Microbial Origin: An Updated Review, Mini-Reviews in Medicinal Chemistry (2024)
48. 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)
49. Synthetic Approaches and Structural Diversity of Triazolylbutanols Derived From Voriconazole in the Antifungal Drug Development, European Journal of Medicinal Chemistry (2022)
50. Design, Synthesis and Biological Activity of Hybrid Antifungals Derived From Fluconazole and Mebendazole, European Journal of Medicinal Chemistry (2023)