Synthesis of Palladium-Catalysed C-C Bond Forming 5-Chloro Quinolines via Suzuki-Miyaura Coupling; Anti-Pancreatic Cancer Screening on PANC-1 Cell Lines.
| Title: | Synthesis of Palladium-Catalysed C-C Bond Forming 5-Chloro Quinolines via Suzuki-Miyaura Coupling; Anti-Pancreatic Cancer Screening on PANC-1 Cell Lines. |
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| Authors: | Rahman A; Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Center, Kadur, Chikkamagaluru, Karnataka, India -, 577548.; Ningegowda NB; Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Center, Kadur, Chikkamagaluru, Karnataka, India -, 577548.; Siddappa MK; Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Center, Kadur, Chikkamagaluru, Karnataka, India -, 577548.; Pargi M; Laboratory of Experimental Medicine, Department of Biotechnology, Kuvempu University, Shankargatta, Shimoga, Karnataka, India -, 577451.; Kumaraswamy HM; Laboratory of Experimental Medicine, Department of Biotechnology, Kuvempu University, Shankargatta, Shimoga, Karnataka, India -, 577451.; Satyanarayan ND; Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Center, Kadur, Chikkamagaluru, Karnataka, India -, 577548.; Achur R; Department of Biochemistry, Kuvempu University, Shankargatta, Shimoga, Karnataka, India -, 577451. |
| Source: | Chemistry & biodiversity [Chem Biodivers] 2023 Jan; Vol. 20 (1), pp. e202200622. Date of Electronic Publication: 2022 Dec 13. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: Verlag Helvetica Chimica Acta Country of Publication: Switzerland NLM ID: 101197449 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1612-1880 (Electronic) Linking ISSN: 16121872 NLM ISO Abbreviation: Chem Biodivers Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Zürich, Switzerland : Hoboken, NJ : Verlag Helvetica Chimica Acta ; Distributed in the USA by Wiley, c2004- |
| MeSH Terms: | Quinolines*/chemistry ; Neoplasms*; Palladium/chemistry ; Humans ; Molecular Structure ; Early Detection of Cancer ; Cell Line ; Ligands ; Pyridines ; Pancreatic Neoplasms |
| Abstract: | Pancreatic cancer is the most severe among other cancers due to its late detection and less chance of survivability. Heterocycles are proven ring systems in the treatment of various cancers and this is due to the presence of two biodynamic molecules combined, which have a greater synergistic efficacy in many anticancer drugs. Quinoline and pyridine ring systems are brought together to obtain greater potency and this is achieved by coupling both using Pd-catalyst, and in the present investigation, Suzuki-Miyaura coupling (SMC) reactions are adopted to generate potent molecular entities. Pancreatic cancer is difficult to treat due to overexpression of the VEGFR2 protein. VEGFR2 is targeted to design the molecules of quinoline-coupled pyridine moieties and is docked to evaluate the protein-ligand interaction at the binding site. The binding affinity of conjugates revealed the potency and capability of ligands to inhibit the VEGFR2 pathway. The in-silico ADMET properties determined their inherent pharmacokinetic feasibility. The synthesized conjugates have been evaluated by MTT assay against the human pancreatic cancer cell lines (PANC-1). Among the series, compounds 5d, 5e, and 5h exhibited a greater inhibitory activity against the cell lines with an IC50 value of 82.32±1.38, 54.74±1.18 and 80.35±1.68 μM. In the present exploration, 5e exhibited greater inhibitory activity and it could be a promising lead for the development of new chemotherapeutics against pancreatic cancer.; (© 2022 Wiley-VHCA AG, Zurich, Switzerland.) |
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| Contributed Indexing: | Keywords: EGFR; VEGFR2; angiogenesis; clioquinol; cytotoxicity; tyrosine kinase receptor |
| Substance Nomenclature: | 5TWQ1V240M (Palladium); 0 (Quinolines); 0 (Ligands); 0 (Pyridines) |
| Entry Date(s): | Date Created: 20221128 Date Completed: 20230124 Latest Revision: 20231213 |
| Update Code: | 20260130 |
| DOI: | 10.1002/cbdv.202200622 |
| PMID: | 36437502 |
| Database: | MEDLINE |
Journal Article