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Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

Bosque, Irene ; Gonzalez-Gomez, Jose C ; Loza, María Isabel ; Brea, José

Journal of organic chemistry, 2014-05, Vol.79 (9), p.3982-3991 [Periódico revisado por pares]

United States: American Chemical Society

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Título:
Natural Tetraponerines: A General Synthesis and Antiproliferative Activity
Autor: Bosque, Irene ; Gonzalez-Gomez, Jose C ; Loza, María Isabel ; Brea, José
Assuntos: Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological Products - chemical synthesis ; Biological Products - chemistry ; Biological Products - pharmacology ; Cell Proliferation - drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Heterocyclic Compounds, 3-Ring - chemical synthesis ; Heterocyclic Compounds, 3-Ring - chemistry ; Heterocyclic Compounds, 3-Ring - pharmacology ; Humans ; MCF-7 Cells ; Molecular Conformation ; Stereoisomerism ; Structure-Activity Relationship
É parte de: Journal of organic chemistry, 2014-05, Vol.79 (9), p.3982-3991
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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Descrição: A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5–6–5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6–6–5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7.
Editor: United States: American Chemical Society
Idioma: Inglês

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Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

Bosque, Irene ; Gonzalez-Gomez, Jose C ; Loza, María Isabel ; Brea, José

United States: American Chemical Society

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