Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation
β-carboline consists of a pyridine ring fused to an indole skeleton; it possesses numerous pharmacological activities, including anticancer. Previously, we reported a satisfactory 2D and 3D QSAR study on β-carboline derivatives. Based on QSAR studies, we designed, synthesized, characterized, and scr...
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MDPI AG
2022-10-01
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| Series: | Chemistry |
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| Online Access: | https://www.mdpi.com/2624-8549/4/4/91 |
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| author | Ravindra Kumar Chourasiya Ram Kishore Agrawal Ankur Vaidya |
| author_facet | Ravindra Kumar Chourasiya Ram Kishore Agrawal Ankur Vaidya |
| author_sort | Ravindra Kumar Chourasiya |
| collection | DOAJ |
| description | β-carboline consists of a pyridine ring fused to an indole skeleton; it possesses numerous pharmacological activities, including anticancer. Previously, we reported a satisfactory 2D and 3D QSAR study on β-carboline derivatives. Based on QSAR studies, we designed, synthesized, characterized, and screened fourteen β-carboline derivatives for anticancer activity. Eleven of them demonstrated potent anticancer activity against both liver (HepG2) and adenocarcinoma (A549) cell lines. Compound 1-(<i>N</i>, <i>N</i>-dimethylbenzenamine)-3-(4-(p-tolylmethanimine)-5-thio-1, 2, 4-triazol-3-yl) β-carboline (<b>9</b>) was found to be most potent against both cancer cell lines and equipotent towards standard drug Adriamycin. Compounds 1-(p-tolyl)-3-(4-(p-(iminomethyl)-<i>N</i>, <i>N</i>-dimethylbenzenamine) -5-thio-1, 2, 4-triazol-3-yl) β-carboline (<b>4</b>) and 1-(<i>N</i>, <i>N</i>-dimethylbenzenamine)-3-(4-(m-tolylmethanimine)-5-thio-1, 2, 4-triazol-3-yl) β-carboline (<b>10</b>) were found to be 7 to 10 times less potent as compared to Adriamycin against the HepG2 cell line. Molecular docking was also performed with the Glide docking program to explore the binding mode between the synthesized β-carboline derivatives and the receptor CDK2 [1AQ1] protein. |
| first_indexed | 2024-03-09T17:12:24Z |
| format | Article |
| id | doaj.art-6e05f6ed06fb4c6da9ccfc6579821fa5 |
| institution | Directory Open Access Journal |
| issn | 2624-8549 |
| language | English |
| last_indexed | 2024-03-09T17:12:24Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry |
| spelling | doaj.art-6e05f6ed06fb4c6da9ccfc6579821fa52023-11-24T13:58:32ZengMDPI AGChemistry2624-85492022-10-01441395140610.3390/chemistry4040091Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological EvaluationRavindra Kumar Chourasiya0Ram Kishore Agrawal1Ankur Vaidya2Department of Pharmaceutical Sciences, Dr. Harisingh Gour University, Sagar 470003, MP, IndiaDepartment of Pharmaceutical Sciences, Dr. Harisingh Gour University, Sagar 470003, MP, IndiaFaculty of Pharmacy, Uttar Pradesh University of Medical Sciences, Saifai, Etawah 206130, UP, Indiaβ-carboline consists of a pyridine ring fused to an indole skeleton; it possesses numerous pharmacological activities, including anticancer. Previously, we reported a satisfactory 2D and 3D QSAR study on β-carboline derivatives. Based on QSAR studies, we designed, synthesized, characterized, and screened fourteen β-carboline derivatives for anticancer activity. Eleven of them demonstrated potent anticancer activity against both liver (HepG2) and adenocarcinoma (A549) cell lines. Compound 1-(<i>N</i>, <i>N</i>-dimethylbenzenamine)-3-(4-(p-tolylmethanimine)-5-thio-1, 2, 4-triazol-3-yl) β-carboline (<b>9</b>) was found to be most potent against both cancer cell lines and equipotent towards standard drug Adriamycin. Compounds 1-(p-tolyl)-3-(4-(p-(iminomethyl)-<i>N</i>, <i>N</i>-dimethylbenzenamine) -5-thio-1, 2, 4-triazol-3-yl) β-carboline (<b>4</b>) and 1-(<i>N</i>, <i>N</i>-dimethylbenzenamine)-3-(4-(m-tolylmethanimine)-5-thio-1, 2, 4-triazol-3-yl) β-carboline (<b>10</b>) were found to be 7 to 10 times less potent as compared to Adriamycin against the HepG2 cell line. Molecular docking was also performed with the Glide docking program to explore the binding mode between the synthesized β-carboline derivatives and the receptor CDK2 [1AQ1] protein.https://www.mdpi.com/2624-8549/4/4/91β-carbolinepharmacophoreQSAR[(SW) kNN MFA]dockingsynthesis |
| spellingShingle | Ravindra Kumar Chourasiya Ram Kishore Agrawal Ankur Vaidya Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation Chemistry β-carboline pharmacophore QSAR [(SW) kNN MFA] docking synthesis |
| title | Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation |
| title_full | Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation |
| title_fullStr | Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation |
| title_full_unstemmed | Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation |
| title_short | Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation |
| title_sort | promising anticancer activity of β carboline derivatives design synthesis and pharmacological evaluation |
| topic | β-carboline pharmacophore QSAR [(SW) kNN MFA] docking synthesis |
| url | https://www.mdpi.com/2624-8549/4/4/91 |
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