3-[N-(tert-butoxycarbonyl)-L-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione | 642471-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[N-(tert-butoxycarbonyl)-L-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione
• 英文别名: ethyl 3-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4,9-dioxo-2H-benzo[f][1]benzothiole-3-carboxylate
• CAS: 642471-95-2
• 化学式: C₂₃H₂₆N₂O₇S
• 分子量: 474.535
• InChiKey: BGEMDRPZLCMNSJ-AKYMPMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[N-(tert-butoxycarbonyl)-L-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以86%的产率得到3-(L-alanyl)amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione hydrochloride
  参考文献：
  名称：

  New benzo[g]isoquinoline-5,10-diones and dihydrothieno [2,3-b]naphtho-4,9-dione derivatives

  摘要：

  Novel antitumoral agents with quinonic structure were synthesized and evaluated for their in vitro cytotoxic activities. This study examines the cytotoxic activities of several aryl benzo[g]isoquinoline-5,10-dione derivatives and a number of aminoacyl dihydrothieno[2,3-b]naphtho-4.9-dione (DTNQ) derivatives containing amino acids in position 3 of the ring system. Compound 6 showed remarkable cytotoxic activity at submicromolar concentration not only against several human leukaemia and solid tumour cell lines, but also toward sensitive and resistant human cell lines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00310-9
• 作为产物：
  描述：

  ethyl (4R)-2-(3-nitrophenyl)-1,3-thiazolidine-4-carboxylate 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 3-[N-(tert-butoxycarbonyl)-L-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione
  参考文献：
  名称：

  New benzo[g]isoquinoline-5,10-diones and dihydrothieno [2,3-b]naphtho-4,9-dione derivatives

  摘要：

  Novel antitumoral agents with quinonic structure were synthesized and evaluated for their in vitro cytotoxic activities. This study examines the cytotoxic activities of several aryl benzo[g]isoquinoline-5,10-dione derivatives and a number of aminoacyl dihydrothieno[2,3-b]naphtho-4.9-dione (DTNQ) derivatives containing amino acids in position 3 of the ring system. Compound 6 showed remarkable cytotoxic activity at submicromolar concentration not only against several human leukaemia and solid tumour cell lines, but also toward sensitive and resistant human cell lines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00310-9

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.