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Preparation of S14161 and Its Analogues and the Discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a More Potent Antitumor Agent in Vitro

Preparation of S14161 and Its Analogues and the Discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a More Potent Antitumor Agent in Vitro

Shu-Qiang Yin, Min Shi, Ting-Ting Kong, Cheng-Mei Zhang, Kunkun Han, Biyin Cao, Zubin Zhang, Xiaolin Du, Long-Qian Tang, Xinliang Mao, Zhao-Peng Liu

Bioorg Med Chem Lett. 2013 Jun 1;23(11):3314-9.

PMID: 23601711

Abstract:

The small chemical compound 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) was recently identified as an inhibitor of the phosphoinositide 3-kinase (PI3K). In the present study, we designed a novel synthesis of S14161 and prepared a series of its analogues via the oxa-Michael-Henry reaction in the presence of catalytic amounts of l-proline and triethylamine. Further structural simplification led to the identification of 6-bromo-8-ethoxy-3-nitro-2H-chromene (BENC-511) that exhibited potent antiproliferative activities against a panel of 12 tumor cell lines. Compared with S14161, BENC-511 was more potent in blocking the AKT phosphorylation and inducing cancer cell apoptosis. BENC-511 also displayed more potent effects on human umbilical vein epithelial cells (HUVEC) migration, suggesting its anti-angiogenesis activity.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP883046502	S14161		883046-50-2	Price

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