3-[(β-alanyl)amino]naphtho[2,3-b]thiophene-4,9-dione trifluoroacetate | 1309667-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[(β-alanyl)amino]naphtho[2,3-b]thiophene-4,9-dione trifluoroacetate
• 英文别名: 3-amino-N-(4,9-dioxobenzo[f][1]benzothiol-3-yl)propanamide;2,2,2-trifluoroacetic acid
• CAS: 1309667-55-7
• 化学式: C₂HF₃O₂*C₁₅H₁₂N₂O₃S
• 分子量: 414.362
• InChiKey: WBFRIIZROPKMQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-[N-(tert-butoxycarbonyl)-β-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione 在 三乙基硅烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 3-[(β-alanyl)amino]naphtho[2,3-b]thiophene-4,9-dione trifluoroacetate
  参考文献：
  名称：

  Design, Synthesis, and Cytotoxic Evaluation of Acyl Derivatives of 3-Aminonaphtho[2,3-b]thiophene-4,9-dione, a Quinone-Based System

  摘要：

  A series of 3-acyl derivatives of the dihydronaphtho[2,3-b]thiophen-4,9-dione system were studied with respect to cytotoxicity and topoisomerase II inhibitory activity. These analogues were designed as electron-deficient anthraquinone analogues with potential intercalation ability. Derivatives 3-(diethylamino)-N-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)propanamide (11m) and 3-(2-(dimethyl-amino)ethylamino)-N-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)propanamide (11p) showed a high efficacy in cell lines that were highly resistant to treatment with doxorubicin, such as MDA-MB435 (melanoma), IGROV (ovarian), and SF-295 (glioblastoma) human cell lines. Both compounds inhibit topoisomerase II mediated relaxation of DNA, while only 11p incites arrest at the S phase in Caco-2 cells, inducing a delay of cell cycle progression and an increase of cell differentiation. The ability of these derivatives to modulate small heat shock proteins and cardiotoxicy effects was also explored. In addition, the DNA-binding properties of these compounds were investigated and discussed.

  DOI：

  10.1021/jm200094h

文献信息

• Design, Synthesis, and Cytotoxic Evaluation of Acyl Derivatives of 3-Aminonaphtho[2,3-<i>b</i>]thiophene-4,9-dione, a Quinone-Based System
  作者：Isabel Gomez-Monterrey、Pietro Campiglia、Claudio Aquino、Alessia Bertamino、Ilaria Granata、Alfonso Carotenuto、Diego Brancaccio、Paola Stiuso、Ilaria Scognamiglio、M. Rosaria Rusciano、Angela Serena Maione、Maddalena Illario、Paolo Grieco、Bruno Maresca、Ettore Novellino

  DOI：10.1021/jm200094h

  日期：2011.6.23

  A series of 3-acyl derivatives of the dihydronaphtho[2,3-b]thiophen-4,9-dione system were studied with respect to cytotoxicity and topoisomerase II inhibitory activity. These analogues were designed as electron-deficient anthraquinone analogues with potential intercalation ability. Derivatives 3-(diethylamino)-N-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)propanamide (11m) and 3-(2-(dimethyl-amino)ethylamino)-N-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)propanamide (11p) showed a high efficacy in cell lines that were highly resistant to treatment with doxorubicin, such as MDA-MB435 (melanoma), IGROV (ovarian), and SF-295 (glioblastoma) human cell lines. Both compounds inhibit topoisomerase II mediated relaxation of DNA, while only 11p incites arrest at the S phase in Caco-2 cells, inducing a delay of cell cycle progression and an increase of cell differentiation. The ability of these derivatives to modulate small heat shock proteins and cardiotoxicy effects was also explored. In addition, the DNA-binding properties of these compounds were investigated and discussed.