1-(2-(dimethylamino)ethyl)-3-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)urea | 1309751-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-(dimethylamino)ethyl)-3-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)urea
• 英文别名: 1-[2-(Dimethylamino)ethyl]-3-(4,9-dioxobenzo[f][1]benzothiol-3-yl)urea
• CAS: 1309751-85-6
• 化学式: C₁₇H₁₇N₃O₃S
• 分子量: 343.406
• InChiKey: UNDHBOZWNFFIRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-(dimethylamino)ethyl)-3-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)urea 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 1-(2-(dimethylamino)ethyl)-3-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)urea hydrochloride
  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
• 作为产物：
  描述：

  3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 1-(2-(dimethylamino)ethyl)-3-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)urea
  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.