Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents
A new series of N-substituted azetidinones (9a–h) synthesized by condensation of 4-arylidene hydrazino 1-isobutyl-1H-imidazo[4,5-c]quinolines (8a–h) with chloroacetyl chloride afforded 4-arylazetidin-2-ones (9a–h). The synthesized compounds were characterized by 1H NMR, 13C NMR, mass spectral and el...
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| Format: | Article |
| Language: | English |
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Elsevier
2017-01-01
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| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610314001264 |
| _version_ | 1818023248271507456 |
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| author | Reshma Kayarmar G.K. Nagaraja Prashantha Naik H. Manjunatha B.C. Revanasiddappa T. Arulmoli |
| author_facet | Reshma Kayarmar G.K. Nagaraja Prashantha Naik H. Manjunatha B.C. Revanasiddappa T. Arulmoli |
| author_sort | Reshma Kayarmar |
| collection | DOAJ |
| description | A new series of N-substituted azetidinones (9a–h) synthesized by condensation of 4-arylidene hydrazino 1-isobutyl-1H-imidazo[4,5-c]quinolines (8a–h) with chloroacetyl chloride afforded 4-arylazetidin-2-ones (9a–h). The synthesized compounds were characterized by 1H NMR, 13C NMR, mass spectral and elemental analyses. All synthesized compounds were screened for their in vitro antimicrobial and anticancer activities. The hydrazone derivatives (8a–h) showed good antibacterial activity. Compounds 9a and 9b exhibited good anticancer activity. In a molecular docking study compounds 9a and 9b showed minimum binding energy and good affinity towards the active pocket. Thus, are believed to be good inhibitors of β-tubulin. |
| first_indexed | 2024-12-10T03:41:18Z |
| format | Article |
| id | doaj.art-d3664b433b8d4851abd340a5f18eb26a |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-12-10T03:41:18Z |
| publishDate | 2017-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-d3664b433b8d4851abd340a5f18eb26a2022-12-22T02:03:34ZengElsevierJournal of Saudi Chemical Society1319-61032017-01-0121S1S434S44410.1016/j.jscs.2014.07.003Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agentsReshma Kayarmar0G.K. Nagaraja1Prashantha Naik2H. Manjunatha3B.C. Revanasiddappa4T. Arulmoli5Department of Chemistry, Mangalore University, Mangalagangotri 574199, IndiaDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, IndiaDepartment of Biosciences, Mangalore University, Mangalagangotri 574199, IndiaDepartment of P.G. Studies and Research in Biotechnology and Bioinformatics, Kuvempu University, Shankaraghatta 577451, Karnataka, IndiaDepartment of Pharmaceutical Chemistry, NGSM Institute of Pharmaceutical Science Paneer, Deralakatte Mangalore 575018, Karnataka, IndiaDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, IndiaA new series of N-substituted azetidinones (9a–h) synthesized by condensation of 4-arylidene hydrazino 1-isobutyl-1H-imidazo[4,5-c]quinolines (8a–h) with chloroacetyl chloride afforded 4-arylazetidin-2-ones (9a–h). The synthesized compounds were characterized by 1H NMR, 13C NMR, mass spectral and elemental analyses. All synthesized compounds were screened for their in vitro antimicrobial and anticancer activities. The hydrazone derivatives (8a–h) showed good antibacterial activity. Compounds 9a and 9b exhibited good anticancer activity. In a molecular docking study compounds 9a and 9b showed minimum binding energy and good affinity towards the active pocket. Thus, are believed to be good inhibitors of β-tubulin.http://www.sciencedirect.com/science/article/pii/S1319610314001264ImidazoquinolineHydrazoneAzetidinoneAntimicrobial activityAnticancer activityβ-TubulinDocking study |
| spellingShingle | Reshma Kayarmar G.K. Nagaraja Prashantha Naik H. Manjunatha B.C. Revanasiddappa T. Arulmoli Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents Journal of Saudi Chemical Society Imidazoquinoline Hydrazone Azetidinone Antimicrobial activity Anticancer activity β-Tubulin Docking study |
| title | Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents |
| title_full | Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents |
| title_fullStr | Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents |
| title_full_unstemmed | Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents |
| title_short | Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents |
| title_sort | synthesis and characterization of novel imidazoquinoline based 2 azetidinones as potent antimicrobial and anticancer agents |
| topic | Imidazoquinoline Hydrazone Azetidinone Antimicrobial activity Anticancer activity β-Tubulin Docking study |
| url | http://www.sciencedirect.com/science/article/pii/S1319610314001264 |
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