3-(N-tert-butyloxyalanyl)aminonaphtho[2,3-b]thiophene-4,9-dione | 1215117-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(N-tert-butyloxyalanyl)aminonaphtho[2,3-b]thiophene-4,9-dione
• 英文别名: tert-butyl N-[(2S)-1-[(4,9-dioxobenzo[f][1]benzothiol-3-yl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 1215117-93-3
• 化学式: C₂₀H₂₀N₂O₅S
• 分子量: 400.455
• InChiKey: QGMXJXCDMDKELM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(N-tert-butyloxyalanyl)aminonaphtho[2,3-b]thiophene-4,9-dione 、 三氟乙酸 在 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到3-[(L-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
• 作为产物：
  描述：

  3-[N-(tert-butoxycarbonyl)-L-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到3-(N-tert-butyloxyalanyl)aminonaphtho[2,3-b]thiophene-4,9-dione
  参考文献：
  名称：

  Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based α,α-amino esters

  摘要：

  描述了一种从相应的α,α-氨基酸酯合成新型醌基胺及其衍生物的非同寻常且高效的合成方法。该过程涉及在碱性水解过程中通过氢转移实现醌基体系的氧化脱羧。这种合成方法以良好的产率，快速地合成出可能具有细胞毒性的新型醌类化合物。

  DOI：

  10.1039/b918898c

文献信息

• Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based α,α-amino esters
  作者：Pietro Campiglia、Claudio Aquino、Alessia Bertamino、Nicoletta De Simone、Marina Sala、Sabrina Castellano、Marisabella Santoriello、Paolo Grieco、Ettore Novellino、Isabel M. Gomez-Monterrey

  DOI：10.1039/b918898c

  日期：——

  An unusual and efficient method for the synthesis of new quinone-based amine and its derivatives from the corresponding α,α-amino ester is described. The procedure involves the quinone-based system's oxidative decarboxylation via hydride transfer throughout basic hydrolysis. This synthetic method provides, with good yields, rapid access to new potentially cytotoxic quinones.

  描述了一种从相应的α,α-氨基酸酯合成新型醌基胺及其衍生物的非同寻常且高效的合成方法。该过程涉及在碱性水解过程中通过氢转移实现醌基体系的氧化脱羧。这种合成方法以良好的产率，快速地合成出可能具有细胞毒性的新型醌类化合物。
• 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.