4-chloro-1,2-dimethyl-6,7-dihydro-1H-indole-5-carbaldehyde | 853730-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-1,2-dimethyl-6,7-dihydro-1H-indole-5-carbaldehyde
• 英文别名: 4-Chloro-1,2-dimethyl-6,7-dihydroindole-5-carbaldehyde
• CAS: 853730-78-6
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: YENWLEVXCBSZJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-1,2-dimethyl-6,7-dihydro-1H-indole-5-carbaldehyde 在 potassium tert-butylate 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (E)-3-(4-Ethylsulfanyl-1,2-dimethyl-1H-indol-5-yl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and photochemotherapeutic activity of thiopyrano[2,3-e]indol-2-ones

  摘要：

  A series of derivatives of the new ring system thiopyrano[2,3-e]indol-2-one was prepared with the aim of obtaining new photochemotherapeutic drugs. Biological screenings were performed on this new class of photoactivable drugs and a strong anti-proliferative effect was observed upon irradiation with UVA light. The compound bearing a methyl substituent at the pyrrole nitrogen resulted as the most interesting showing IC50 in the nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.016
• 作为产物：
  描述：

  4-oxo-1-methyl-2-methyl-4,5,6,7-tetrahydroindole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 4-chloro-1,2-dimethyl-6,7-dihydro-1H-indole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis and photochemotherapeutic activity of thiopyrano[2,3-e]indol-2-ones

  摘要：

  A series of derivatives of the new ring system thiopyrano[2,3-e]indol-2-one was prepared with the aim of obtaining new photochemotherapeutic drugs. Biological screenings were performed on this new class of photoactivable drugs and a strong anti-proliferative effect was observed upon irradiation with UVA light. The compound bearing a methyl substituent at the pyrrole nitrogen resulted as the most interesting showing IC50 in the nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.016

文献信息

• Thiopyrano[2,3-e]indol-2-ones: Angelicin heteroanalogues with potent photoantiproliferative activity
  作者：Paola Barraja、Patrizia Diana、Alessandra Montalbano、Anna Carbone、Girolamo Cirrincione、Giampietro Viola、Alessia Salvador、Daniela Vedaldi、Francesco Dall’Acqua

  DOI：10.1016/j.bmc.2008.10.002

  日期：2008.11

  A new class of compounds, the thiopyrano[2,3-e]indol-2-ones, bioisosters of the angular furocoumarin angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents. In particular 7,8-dimethyl-thiopyranoindolone 6c s showed a remarkable phototoxicity and a great dose UVA dependence reaching IC(50) values at submicromolar level. This latter photoinduced a massive apoptosis and

  为了获得新的光化学治疗剂，合成了一类新的化合物，即角呋喃香豆素当归的生物等位基因thiopyrano [2,3-e] indol-2-ones。特别是7,8-二甲基-硫代吡喃并吲哚酮6c s表现出了显着的光毒性，并且在亚微摩尔水平上对UVA的依赖性很大，达到了IC（50）值。后者光诱导大量的细胞凋亡，并对脂质和蛋白质产生显着的光损伤。尽管它不插入DNA，但它能够引起DNA碱基的光氧化。