ethyl 3-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate | 1092546-11-6

• 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: ethyl 3-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate
• 英文别名: ethyl 3-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-4,9-dioxo-2H-thieno[2,3-g]quinoline-3-carboxylate
• CAS: 1092546-11-6
• 化学式: C₂₈H₂₉N₃O₇S
• 分子量: 551.62
• InChiKey: OASXJGLEKFDQIA-BVFFRPSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate 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71%的产率得到3-(N-tert-butyloxylphenylalanyl)aminothiophene [2,3-g]quinoline-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
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 ethyl 3-amino-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 3-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate
  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

• Antitumor Agents 6. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Spiro[imidazolidine-4,3′-thieno[2,3-<i>g</i>]quinoline]-tetraones and Spiro[thieno[2,3-<i>g</i>]quinoline-3,5′-[1,2,4]triazinane]-tetraones with Potent Antiproliferative Activity
  作者：Adele Bolognese、Gaetano Correale、Michele Manfra、Anna Esposito、Ettore Novellino、Antonio Lavecchia

  DOI：10.1021/jm8007689

  日期：2008.12.25

  Two series of quinolinquinone derivatives, 2'H-spiro[imidazolidine-4,3'-thieno[2,3-g]quinoline]-2,4',5,9'-tetraones (2a-n) and 2H-spiro[thieno[2,3-g]quinoline-3.5'-[1,2,4]triazinane]-3',4,6',9-tetraones (3a-e), were designed and synthesized using the previously described ethyl 3-amino-4,9-dioxo-2,3,4,9-tetrahydrothieno[2,3-g]quinoline-3-carboxylate (1) as a starting material. All compounds were evaluated for their anti proliferative activity against a panel of representative liquid and solid human tumor cell lines and exhibit IC(50) values in the micromolar/submicromolar range. Series 2 displayed higher cytotoxicity than did series 3. The nature of the substituents on both imidazoline and triazinane N1 nitrogen markedly affected the activity profile of these series. Spectrophotometric and fluorescence measurements as well as Unwinding assays performed on the most cytotoxic compounds, 2c, 2g, and 2k, showed that they are nonintercalative DNA agents and inhibit the catalytic activity of Topo II in a concentration-dependent mode. 2g was the most active Topo II inhibitor with activity levels comparable to those of VP-16.
• 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。