ethyl 2-diazo-2H-indole-3-carboxylate | 869844-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: ethyl 2-diazo-2H-indole-3-carboxylate
• 英文别名: Ethyl 2-diazoindole-3-carboxylate
• CAS: 869844-16-6
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: PCVBBVPSSDBLSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-2H-indole-3-carboxylate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以100%的产率得到3-(ethoxycarbonyl)-1H-indole-2-diazonium chloride
  参考文献：
  名称：

  2-Diazo-2H-indoles

  摘要：

  2-Diazo-2H-indoles were prepared by diazotization of the corresponding 1H-indol-2-amines and subsequent neutralization. On the basis of NMR data and ab initio, and semiempirical calculations, we suggest that the zwitterionic form A is the most representative structure for 2-diazo-2H-indoles. In fact, spectral data are compatible with a IH-indole structure, and the fully optimized molecules gave distances in agreement with those reported for the anion obtained from 1H-indole. The calculated charges are compatible with a zwitterionic structure in which the negative charge is mainly located at the ring N-atom at variance with the case of diazopyrroles and 3-diazo-3H-indoles where the negative charge is essentially located on the ipso C-atom.

  DOI：

  10.1002/1522-2675(20010815)84:8<2212::aid-hlca2212>3.0.co;2-s
• 作为产物：
  描述：

  2-氨基吲哚-3-羧酸乙酯 在 sodium nitrite 、 sodium carbonate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 3.0h， 以60%的产率得到ethyl 2-diazo-2H-indole-3-carboxylate
  参考文献：
  名称：

  2-Diazo-2H-indoles

  摘要：

  2-Diazo-2H-indoles were prepared by diazotization of the corresponding 1H-indol-2-amines and subsequent neutralization. On the basis of NMR data and ab initio, and semiempirical calculations, we suggest that the zwitterionic form A is the most representative structure for 2-diazo-2H-indoles. In fact, spectral data are compatible with a IH-indole structure, and the fully optimized molecules gave distances in agreement with those reported for the anion obtained from 1H-indole. The calculated charges are compatible with a zwitterionic structure in which the negative charge is mainly located at the ring N-atom at variance with the case of diazopyrroles and 3-diazo-3H-indoles where the negative charge is essentially located on the ipso C-atom.

  DOI：

  10.1002/1522-2675(20010815)84:8<2212::aid-hlca2212>3.0.co;2-s

文献信息

• Synthesis and antiproliferative activity of [1,2,3,5]tetrazino[5,4-a]indoles, a new class of azolo-tetrazinones
  作者：Paola Barraja、Patrizia Diana、Antonino Lauria、Alessandra Montalbano、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione

  DOI：10.1016/j.bmc.2004.10.028

  日期：2005.1

  Eight derivatives of the new ring system [1,2,3,5]tetrazino[5,4-a]indole-4-one 7, were synthesised in good yields by reaction of 2-diazoindoles with alkyl or aryl isocyanates. Compounds 7 were screened at National Cancer Institute (NCI) for their activity against a panel of approximately 60 human tumour cell lines. Some of them showed antiproliferative activity having generally GI(50) in the micromolar range. The most sensitive cell lines were SF-295, SNB-75 and SF-539 of the CNS cancer sub-panel, SR of the leukaemia sub-panel, UACC-62 of the melanoma sub-panel and OVCAR-4 of the ovarian cancer sub-panel. (C) 2004 Elsevier Ltd. All rights reserved.