9-methyl-1,3,4,9-tetrahydro-2H-carbazol-2-one | 75142-86-8

• 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: 9-methyl-1,3,4,9-tetrahydro-2H-carbazol-2-one
• 英文别名: 9-methyl-2-oxo-1,2,3,4-tetrahydrocarbazole；9-methyl-3,4-dihydro-1H-carbazol-2-one
• CAS: 75142-86-8
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: SJXAFZQBNABECG-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C(Solv: ethanol (64-17-5))
• 沸点：
  398.2±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  p-chlorobenzenesulfonyl azide 、 9-methyl-1,3,4,9-tetrahydro-2H-carbazol-2-one 以 二甲基亚砜 为溶剂， 反应 48.0h， 以55%的产率得到2-p-chlorophenylsulphonylimino-1-methyl-3'-oxoindoline-3-spirocyclopentane
  参考文献：
  名称：

  某些四氢-β-咔啉，六氢氮杂环庚烷[3,4- b ]吲哚和四氢咔唑酮与芳磺酰叠氮化物的反应

  摘要：

  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。

  DOI：

  10.1039/p19800001512
• 作为产物：
  描述：

  苯肼 在 对甲苯磺酸一水合物 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 58.17h， 生成 9-methyl-1,3,4,9-tetrahydro-2H-carbazol-2-one
  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

文献信息

• Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
  作者：Daniel Clare、Benjamin C. Dobson、Phillip A. Inglesby、Christophe Aïssa

  DOI：10.1002/anie.201910821

  日期：2019.11.4

  The functionalization of aryl and heteroaryls using α‐carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α‐carbonyl sulfoxonium ylides onto benzenes, benzofurans and N‐p‐toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles

  尽管亚砜叶立德具有有利的安全性，但在没有导向基团帮助的情况下使用α-羰基亚砜叶立德对芳基和杂芳基进行官能化迄今为止仍然是一个被忽视的领域。本文描述了在 HFIP 中碱存在下，α-羰基亚锍叶立德在苯、苯并呋喃和 N-对甲苯磺酰吲哚上的环化，而吡咯和N-甲基吲哚在铱催化剂存在下进行环化。值得注意的是，这两组条件对于每组底物都是化学特异性的。
• BAILEY A. S.; VANDREVALA M. H., J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 7, 1512-1515
  作者：BAILEY A. S.、 VANDREVALA M. H.

  DOI：——

  日期：——