Compounds > 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene

8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene and triethylenediamine

8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene has been researched along with triethylenediamine* in 1 studies

Other Studies

1 other study(ies) available for 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2h-chromene and triethylenediamine

Article	Year
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. Bioorganic & medicinal chemistry letters, 2013, Jun-01, Volume: 23, Issue:11 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. Topics: Antineoplastic Agents; Benzopyrans; Binding Sites; Catalysis; Cell Line, Tumor; Cell Movement; Cell Proliferation; Drug Evaluation, Preclinical; Drug Screening Assays, Antitumor; Human Umbilical Vein Endothelial Cells; Humans; Molecular Docking Simulation; Neovascularization, Physiologic; Phosphatidylinositol 3-Kinases; Phosphoinositide-3 Kinase Inhibitors; Phosphorylation; Piperazines; Proline; Protein Structure, Tertiary; Proto-Oncogene Proteins c-akt	2013

Article

Year

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.

Bioorganic & medicinal chemistry letters, 2013, Jun-01, Volume: 23, Issue:11

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.

Topics: Antineoplastic Agents; Benzopyrans; Binding Sites; Catalysis; Cell Line, Tumor; Cell Movement; Cell Proliferation; Drug Evaluation, Preclinical; Drug Screening Assays, Antitumor; Human Umbilical Vein Endothelial Cells; Humans; Molecular Docking Simulation; Neovascularization, Physiologic; Phosphatidylinositol 3-Kinases; Phosphoinositide-3 Kinase Inhibitors; Phosphorylation; Piperazines; Proline; Protein Structure, Tertiary; Proto-Oncogene Proteins c-akt

2013