2-Oxo-1,2,3,4-tetrahydrocarbazol | 40429-00-3

• 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: 2-Oxo-1,2,3,4-tetrahydrocarbazol
• 英文别名: 1,3,4,9-tetrahydro-2H-carbazol-2-one；3,4-Dihydro-1H-carbazol-2(9H)-one；1,3,4,9-tetrahydrocarbazol-2-one
• CAS: 40429-00-3
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: LGXBMDJOLNSLEI-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  388.8±42.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Oxo-1,2,3,4-tetrahydrocarbazol 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以70.3%的产率得到(E)-1,3,4,9-tetrahydro-2H-carbazol-2-one oxime
  参考文献：
  名称：

  Discovery of tetrahydrocarbazoles as dual pERK and pRb inhibitors

  摘要：

  The extracellular signal-regulated kinase (ERK) is one of the most important molecular targets for cancer that controls diverse cellular processes such as proliferation, survival, differentiation and motility. Similarly, the Rb (retinoblastoma protein) is a tumor suppressor protein and its function is to prevent excessive cell growth by inhibiting cell cycle progression. When the cell is ready to divide, pRb is phosphorylated, becomes inactive and allows cell cycle progression. Herein, we discovered a new series of tetrahydrocarbazoles as dual inhibitors of pERK and pRb phosphorylation. The in-house small molecule library was screened for inhibition of pERK and pRb phosphorylation, which led to the discovery of tetrahydrocarbazole series of compounds as potential leads. N-(3-methylcyclopenty1)-6-nitro-2,3,4,4a,9,9a-hexahydro-1H-carbazol-2-amine (1) is the dual inhibitor lead identified through screening, displaying inhibition of PERK and pRb phosphorylation with IC50 values of 5.5 and 4.8 mu M, respectively. A short structure-activity relationship (SAR) study has been performed, which identified another dual inhibitor 9-methyl-N-(4-methylbenzy1)-2,3,4,4a,9,9a-hexahydro-1H-carbazol-2-amine (16) with IC50 values 4.4 and 3.5 mu M for inhibition of pERK and pRb phosphorylation, respectively. This compound has a potential for further lead optimization to discover promising molecularly-targeted anticancer agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.062
• 作为产物：
  描述：

  3-吲哚丙酸 在 dirhodium tetraacetate N-甲基吗啉 、 氯甲酸乙酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-Oxo-1,2,3,4-tetrahydrocarbazol
  参考文献：
  名称：

  铑（II）催化从2-吡咯基和3-吲哚基α-重氮-β-酮酸酯和α-重氮酮衍生的类胡萝卜素的分子内插入

  摘要：

  衍生自2-吡咯基乳酸，2-吡咯基丙酸，3-吲哚基乳酸和3-吲哚基丙酸的α-重氮-β-酮酸酯和α-二氮酮在经过催化的乙酸铑（II）处理后，提供了类胡萝卜素衍生的环化产物。

  DOI：

  10.1016/j.tet.2003.12.019

文献信息

• The reactions of some tetrahydro-β-carbolines, of hexahydroazepino[3,4-b]indoles, and of tetrahydrocarbazolones with arenesulphonyl azides
  作者：A. Sydney Bailey、Marazban H. Vandrevala

  DOI：10.1039/p19800001512

  日期：——

  9-dimethyl-1,2,3,4-tetrahydro-β-carboline react with arenesulphonyl azides forming indoline-3-spiropyrrolidines; 2,10-dimethyl-3,4,5,10-tetrahydroazepino[3,4-b]indol-1 (2H)-one and 2,10-dimethyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole react to form indoline-3-spiropiperidines. 9-Methyl-2-oxo-tetrahydrocarbazole reacts with p-chlorobenzenesulphonyl azide to form 1-methyl-2-p-chlorophenylsulphonylimino

  2,9-二甲基-1,2,3,4-四氢-1-氧代-β-咔啉和2,9-二甲基-1,2,3,4-四氢-β-咔啉与芳磺酰叠氮化物反应形成二氢吲哚- 3-螺吡咯烷; 2,10-二甲基-3,4,5,10-四氢氮杂环庚烷[3,4- b ]吲哚-1（2 H）-one和2,10-二甲基-1,2,3,4,5,10-六氢氮杂环庚烷[3,4- b ]吲哚反应形成吲哚啉-3-螺哌啶。9-甲基-2-氧代-四氢咔唑与对氯苯磺酰基叠氮化物反应形成1-甲基-2-对氯苯磺酰氨基-3'-氧代吲哚-3-螺旋环戊烷。
• Intramolecular Carbenoid Insertions: the Reactions of α-Diazoketones Derived from Pyrrolyl and Indolyl Carboxylic Acids with Rhodium(II) Acetate
  作者：Mohamed Salim、Alfredo Capretta

  DOI：10.1016/s0040-4020(00)00725-0

  日期：2000.10

  α-Diazoketones derived from pyrrolyl- and indolyl-carboxylic acids were prepared and their Rh2(OAc)4 catalyzed decomposition chemistry was studied. These reactions generally resulted in the alkylation of the heteroaromatic system by the ketocarbenoid and in some instances the systems underwent CH or NH insertions. Evidence that some of these reactions proceed via a cyclopropane intermediate is presented

  制备了由吡咯基和吲哚基羧酸衍生的α-重氮酮，并研究了其Rh 2（OAc）4催化的分解化学。这些反应通常导致酮类化合物对杂芳族系统进行烷基化，在某些情况下，该系统进行了CH或NH插入。提供了其中一些反应通过环丙烷中间体进行的证据。所描述的方法提供了易于接近稠合的吡咯基-或吲哚基-环烷酮体系的方法，其中羰基为杂芳族系统的β。
• WO2006/89053
  申请人：——

  公开号：——

  公开（公告）日：——
• Gazengel, Jean-Marie; Lancelot, Jean-Charles; Rault, Sylvain, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1135 - 1139
  作者：Gazengel, Jean-Marie、Lancelot, Jean-Charles、Rault, Sylvain、Robba, Max

  DOI：——

  日期：——
• Kumar, Yatendra; Saxena, Anil K.; Jain, Padam C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 11, p. 996
  作者：Kumar, Yatendra、Saxena, Anil K.、Jain, Padam C.、Anand, Nitya

  DOI：——

  日期：——