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2006-05-06

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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/56314

Synthesis and structure - Activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D

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Recurs relacionat

http://dx.doi.org/10.1021/jm0602458

Resum

The marine alkaloid, Lamellarin D (Lam-D), has shown potent cytotoxicity in numerous cancer cell lines, and was recently identified as a potent topoisomerase I inhibitor. A library of open lactone analogs of Lam-D was prepared from a methyl 5,6-dihydropyrrolo[2,1-a]isoquinoline-3- carboxylate scaffold (1) by introducing various aryl groups through sequential and regioselective bromination, followed by Pd(0)-catalyzed Suzuki cross-coupling chemistry. The compounds were obtained in a 24-44% overall yield, and tested in a panel of three human tumor cell lines, MDA-MB- 231 (breast), A-549 (lung), and HT-29 (colon), to evaluate their cytotoxic potential. From these data the SAR study concluded that more than 75% of the open-chain Lam-D analogs tested showed cytotoxicity in a low micromolar GI50 range.

Matèries

Alcaloides, Productes naturals marins, Compostos heterocíclics, Medicaments antineoplàstics, Isoquinolina

Matèries (anglès)

Alkaloids, Marine natural products, Heterocyclic compounds, Antineoplastic agents, Isoquinoline

Citació

Col·leccions

Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Química Inorgànica i Orgànica)

Citació

PLA QUERAL, Daniel, et al. Synthesis and structure - Activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D. Journal of Medicinal Chemistry. 2006. Vol. 49, num. 11, pags. 3257-3268. ISSN 0022-2623. [consulted: 18 of August of 2026]. Available at: https://hdl.handle.net/2445/56314

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