ethyl 1-(phenylsulfonyl)-3-indoleglyoxylate | 116325-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 1-(phenylsulfonyl)-3-indoleglyoxylate
• 英文别名: ethyl 1-(phenylsulfonyl)indole-3-glyoxalate；ethyl 1-(phenylsulfonyl)indole-3-glyoxylate；Ethyl 2-[1-(benzenesulfonyl)indol-3-yl]-2-oxoacetate
• CAS: 116325-16-7
• 化学式: C₁₈H₁₅NO₅S
• 分子量: 357.387
• InChiKey: GEJQBHWBFGHOIB-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  555.5±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 ethyl 1-(phenylsulfonyl)-3-indoleglyoxylate 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.5h， 以77%的产率得到2-羟基-2-(N-(苯基磺酰基)吲哚-3-基)丙酸乙酯
  参考文献：
  名称：

  Synthesis, in vitro antiproliferative activities, and Chk1 inhibitory properties of pyrrolo[3,4-a]carbazole-1,3-diones, pyrrolo[3,4-c]carbazole-1,3-diones, and 2-aminopyridazino[3,4-a]pyrrolo[3,4-c]carbazole-1,3,4,7-tetraone

  摘要：

  The synthesis of substituted pyrrolo[3,4-a]carbazole-1,3-diones, pyrrolo[3,4-c]carbazole-1-,3-diones, and 2-aminopyridazino[3,4-a]pyrrolo[3,4-c]carbazole-1,3,4,7-tetraone is reported. Their inhibitory properties toward Checkpoint I kinase (Chk1) have been evaluated and their in vitro antiproliferative activities toward three tumor cell lines: murine leukemia L1210, human colon carcinoma HT29 and HCT116 have been determined. From the biological results, it appears that, in contrast with the upper E heterocycle, the lower D heterocycle is not absolutely required for Chk1 inhibition. The ATP binding pocket of Chk1 seems to be adaptable to substitution of the nitrogen of the imide E heterocycle with a hydroxymethyl group, allowing the fundamental hydrogen bond with the Glu(85) residue of the enzyme. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.026
• 作为产物：
  描述：

  2-氧代-3-吲哚羧酸乙酯 、 苯磺酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到ethyl 1-(phenylsulfonyl)-3-indoleglyoxylate
  参考文献：
  名称：

  五元芳香杂环作为 Diels-Alder 反应中的亲二烯体。呋喃、吡咯和吲哚

  摘要：

  添加 Diels Alder du butadiene-1,3 et de l'isoprene: 获得 de 衍生 de benzofurane, indole et carbazole; 替代品的效果

  DOI：

  10.1021/ja00229a039

文献信息

• Five-membered aromatic heterocycles as dienophiles in Diels-Alder reactions. Furan, pyrrole, and indole
  作者：Ernest. Wenkert、Peter D. R. Moeller、Serge R. Piettre

  DOI：10.1021/ja00229a039

  日期：1988.10

  Additions Diels Alder du butadiene-1,3 et de l'isoprene: obtention de derives de benzofuranne, indole et carbazole; effets des substituants

  添加 Diels Alder du butadiene-1,3 et de l'isoprene: 获得 de 衍生 de benzofurane, indole et carbazole; 替代品的效果
• DEMOPOULOS, VASSILIS J., SYNTH. COMMUN., 19,(1989) N3-14, C. 2585-2594
  作者：DEMOPOULOS, VASSILIS J.

  DOI：——

  日期：——
• WENKERT, ERNEST;MOELLER, PETER D. R.;PIETTRE, SERGE R., J. AMER. CHEM. SOC., 110,(1988) N 21, C. 7188-7194
  作者：WENKERT, ERNEST、MOELLER, PETER D. R.、PIETTRE, SERGE R.

  DOI：——

  日期：——
• Demopoulos, Vassilis J., Synthetic Communications, 1989, vol. 19, # 13-14, p. 2585 - 2594
  作者：Demopoulos, Vassilis J.

  DOI：——

  日期：——
• Synthesis, in vitro antiproliferative activities, and Chk1 inhibitory properties of pyrrolo[3,4-a]carbazole-1,3-diones, pyrrolo[3,4-c]carbazole-1,3-diones, and 2-aminopyridazino[3,4-a]pyrrolo[3,4-c]carbazole-1,3,4,7-tetraone
  作者：Elisabeth Conchon、Fabrice Anizon、Bettina Aboab、Roy M. Golsteyn、Stéphane Léonce、Bruno Pfeiffer、Michelle Prudhomme

  DOI：10.1016/j.ejmech.2007.03.026

  日期：2008.2

  The synthesis of substituted pyrrolo[3,4-a]carbazole-1,3-diones, pyrrolo[3,4-c]carbazole-1-,3-diones, and 2-aminopyridazino[3,4-a]pyrrolo[3,4-c]carbazole-1,3,4,7-tetraone is reported. Their inhibitory properties toward Checkpoint I kinase (Chk1) have been evaluated and their in vitro antiproliferative activities toward three tumor cell lines: murine leukemia L1210, human colon carcinoma HT29 and HCT116 have been determined. From the biological results, it appears that, in contrast with the upper E heterocycle, the lower D heterocycle is not absolutely required for Chk1 inhibition. The ATP binding pocket of Chk1 seems to be adaptable to substitution of the nitrogen of the imide E heterocycle with a hydroxymethyl group, allowing the fundamental hydrogen bond with the Glu(85) residue of the enzyme. (c) 2007 Elsevier Masson SAS. All rights reserved.