9H-咔唑-2-羧酸 | 51094-28-1

• 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
• 中文名称: 9H-咔唑-2-羧酸
• 英文名称: 9H-carbazole-2-carboxylic acid
• 英文别名: carbazole-2-carboxylic acid；Carbazol-2-carbonsaeure
• CAS: 51094-28-1
• 化学式: C₁₃H₉NO₂
• mdl: MFCD04499966
• 分子量: 211.22
• InChiKey: SNHLDNRYSKNZRC-UHFFFAOYSA-N

物化性质

• 熔点：
  319 °C
• 沸点：
  497.2±18.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9H-咔唑-2-羧酸 在 叠氮磷酸二苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 叔丁醇 、 二氯甲烷 为溶剂， 反应 18.0h， 以38%的产率得到9H-咔唑-2-胺
  参考文献：
  名称：

  Design, synthesis, and evaluation of potent Wnt signaling inhibitors featuring a fused 3-ring system

  摘要：

  The Wnt signaling pathway is a critical developmental pathway which operates through control of cellular functions such as proliferation and differentiation. Aberrant Wnt signaling has been linked to the formation and metastasis of tumors. Porcupine, a member of the membrane -bound O-acyltransferase family of proteins, is an important component of the Wnt pathway. Porcupine catalyzes the palmitoylation of Wnt proteins, a process needed for their secretion and activity. Here we report a novel series of compounds obtained by a scaffold hybridization strategy from a known porcupine inhibitor class. The leading compound 59 demonstrated subnanomolar inhibition of Wnt signaling in a paracrine cellular assay. Compound 59 also showed excellent chemical, plasma and liver microsomal stabilities. Furthermore, compound 59 exhibited good pharmacokinetic profiles with 30% oral bioavailability in rat. Collectively, these results strongly support further optimization of this novel scaffold to develop better Wnt pathway inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.026
• 作为产物：
  描述：

  9H-咔唑-2-甲腈 在 氢氧化钾 作用下， 生成 9H-咔唑-2-羧酸
  参考文献：
  名称：

  DE504341

  摘要：

  公开号：

文献信息

• [EN] FUNCTIONALISED AND SUBSTITUTED CARBAZOLES AS ANTI-CANCER AGENTS<br/>[FR] CARBAZOLES FONCTIONNALISÉS ET SUBSTITUÉS UTILISÉS EN TANT QU'AGENTS ANTI-CANCÉREUX
  申请人：NOVOGEN LTD

  公开号：WO2016008010A1

  公开（公告）日：2016-01-21

  The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a disease or disorder, such as a proliferative disease (preferably cancer), using compounds of the invention.

  本发明涉及抗肌球蛋白化合物，其制备方法，以及利用本发明的化合物治疗或预防疾病或紊乱的方法，如增生性疾病（最好是癌症）。
• CARBAZOLE CARBOXAMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS
  申请人：Liu Qingjie

  公开号：US20100160303A1

  公开（公告）日：2010-06-24

  Compounds having the formula (I), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are useful as kinase modulators, including Btk modulation.

  具有化学式(I)的化合物，以及其对映体、非对映异构体、药用可接受的盐，可用作激酶调节剂，包括Btk调节。
• Synthesis of the Carbazole Scaffold Directly from 2-Aminobiphenyl by Means of Tandem C-H Activation and C-N Bond Formation
  作者：Hans-René Bjørsvik、Vijayaragavan Elumalai

  DOI：10.1002/ejoc.201601191

  日期：2016.11

  An efficient method for the synthesis of the carbazole scaffold was designed and investigated. The method was developed to produce substituted carbazoles by an intramolecular combination of a free amine group and an arene. The steps of the method involved tandem Pd-catalyzed C–H activation and intramolecular C–N bond formation. The method showed good functional group tolerance, and substituent(s) could

  设计并研究了一种合成咔唑支架的有效方法。该方法被开发用于通过游离胺基团和芳烃的分子内组合来生产取代的咔唑。该方法的步骤包括串联 Pd 催化的 C-H 活化和分子内 C-N 键的形成。该方法显示出良好的官能团耐受性，并且取代基可以在2-氨基联苯底物的两个环中的任何一个或两个环上。闭环后，还原的 Pd 催化剂被过氧化氢氧化成 PdII。新方法也被证明可以很好地与相应的 2-N-乙酰氨基联苯一起使用。
• Process of preparing imidazolines
  申请人：IG FARBENINDUSTRIE AG

  公开号：US02176843A1

  公开（公告）日：1939-10-17

  Imidazolines substituted in the 2-position are obtained by condensing N : N1-ethyleneurea, or an N : N1-ethyleneurea substituted at a carbon atom by a hydrocarbon radicle, with a monocarboxylic acid other than formic acid, the reaction occurring with elimination of water and carbon dioxide. In a typical example, N : N1-ethyleneurea and oleic acid, heated to 280-300 DEG C., yield 2-heptadecenyl-imidazoline. Examples are given also of the manufacture of imidazolines from N : N1-ethyleneurea and stearic acid, palmitic acid, benzoic acid, butyric acid, a - and b -naphthoic acids, diphenyl-4-carboxylic acid, carbazole-2-carboxylic acid, and an acid (molecular weight 238) obtained by the oxidation of paraffin. In a further example, N : N1-propylene urea is heated with benzoic acid to yield a mixture of 4- and 5-methyl-2-phenylimidazolines. Carbazole-2-carboxylic acid is obtainable by fusing 2-chloracetyl-N-acetylcarbazole with caustic potash.

  在2-位置取代的咪唑啉可通过将N：N1-乙烯脲或在碳原子上被烃基取代的N：N1-乙烯脲与除甲酸以外的一种单羧酸缩合而得到，反应发生时会排除水和二氧化碳。在一个典型的例子中，将N：N1-乙烯脲和油酸加热至280-300摄氏度，会生成2-十七碳烯基咪唑啉。还提供了从N：N1-乙烯脲和硬脂酸、棕榈酸、苯甲酸、丁酸、α-和β-萘甲酸、二苯基-4-羧酸、咔唑-2-羧酸以及通过对烷烃氧化得到的一种酸（分子量为238）制备咪唑啉的示例。另外，将N：N1-丙烯脲与苯甲酸加热可得到4-和5-甲基-2-苯基咪唑啉的混合物。咔唑-2-羧酸可通过将2-氯乙酰-N-乙酰咔唑与氢氧化钾熔融得到。
• [EN] TETRACYCLIC PYRAZOLE DERIVATIVES AS KINASE INHIBITORS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM<br/>[FR] DERIVES DE PYRAZOLE TETRACYCLIQUE UTILISES COMME INHIBITEURS DE KINASE, PROCESSUS DE PREPARATION CORRESPONDANT ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：PHARMACIA ITALIA SPA

  公开号：WO2004071507A1

  公开（公告）日：2004-08-26

  The present invention provides a method for treating diseases caused by and/or associated with an altered protein kinase activity which comprises administering to a mammal in need thereof an effective amount of a tetracyclic pyrazole. The invention also provides specific tetracyclic pyrazole derivatives, useful intermediates, a library comprising at least two of them, a process for their preparation and the pharmaceutical compositions containing them, which are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, viral infections, autoimmune diseases and neurodegenerative disorders.

  本发明提供了一种治疗由改变的蛋白激酶活性引起和/或与之相关的疾病的方法，包括向需要的哺乳动物施用有效量的四环吡唑。该发明还提供了特定的四环吡唑衍生物、有用的中间体、包含至少两种中间体的库、它们的制备方法以及含有它们的药物组合物，这些药物组合物在治疗由改变的蛋白激酶活性引起和/或与之相关的疾病方面具有用处，如癌症、细胞增殖障碍、病毒感染、自身免疫疾病和神经退行性疾病。