Chemistry of Renieramycins. 15. Synthesis of 22-O-Ester Derivatives of Jorunnamycin A and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cells
| Autor: | Supakarn Chamni, Naoki Saito, Pithi Chanvorachote, Khanit Suwanborirux, Nanae Mori, Natchanun Sirimangkalakitti, Kornvika Charupant |
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| Rok vydání: | 2016 |
| Předmět: |
Stereochemistry
Pharmaceutical Science Antineoplastic Agents Marine Biology Quinolones 010402 general chemistry 01 natural sciences Analytical Chemistry Structure-Activity Relationship Carcinoma Non-Small-Cell Lung Tetrahydroisoquinolines Drug Discovery medicine Animals Humans Cytotoxic T cell Cytotoxicity Lung cancer IC50 Pharmacology Ester derivatives Molecular Structure biology 010405 organic chemistry Chemistry Alkaloid Organic Chemistry Isoquinolines Thailand biology.organism_classification medicine.disease Porifera respiratory tract diseases 0104 chemical sciences Sponge Complementary and alternative medicine Molecular Medicine Non small cell Cisplatin Drug Screening Assays Antitumor |
| Zdroj: | Journal of Natural Products. 79:2089-2093 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.6b00433 |
| Popis: | Eighteen 22-O-ester derivatives of jorunnamycin A (2) were prepared via 2, and their cytotoxicity against human non-small-cell lung cancer (NSCLC) cells was evaluated. Preliminary study of the structure-cytotoxicity relationship revealed that the ester part containing a nitrogen-heterocyclic ring elevated the cytotoxicity of the 22-O-ester derivatives. Among them, 22-O-(4-pyridinecarbonyl) ester 6a is the most potent compound (IC50 1.1 and 1.6 nM), exhibiting 21-fold and 5-fold increases in cytotoxicity against the H292 and H460 NSCLC cell lines, respectively, relative to renieramycin M (1), the major cytotoxic bistetrahydroisoquinolinequinone alkaloid of the Thai blue sponge Xestospongia sp. |
| Databáze: | OpenAIRE |
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