1-chloro-5-methyl-9-methoxy-6H-pyrido<4,3-b>carbazole | 72237-96-8

• 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: 1-chloro-5-methyl-9-methoxy-6H-pyrido<4,3-b>carbazole
• 英文别名: 1-chloro-9-methoxy-5-methyl-6H-pyrido[4,3-b]carbazole
• CAS: 72237-96-8
• 化学式: C₁₇H₁₃ClN₂O
• 分子量: 296.756
• InChiKey: GGEZCLAJEIKELU-UHFFFAOYSA-N

物化性质

• 沸点：
  552.3±45.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.91
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-chloro-5-methyl-9-methoxy-6H-pyrido<4,3-b>carbazole 在 盐酸 、 苄基三乙基氯化铵 、 水 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以90%的产率得到1-chloro-9-hydroxy-5-methyl-6H-pyrido[4,3-b]carbazole
  参考文献：
  名称：

  [EN] PYRIDOCARBAZOLE TYPE COMPOUNDS AND APPLICATIONS THEREOF
  [FR] COMPOSÉ DE TYPE PYRIDOCARBAZOLE ET LEURS APPLICATIONS

  摘要：

  公开号：

  WO2010095042A8
• 作为产物：
  描述：

  9-Methoxy-5-methylpyrido<4,3-b>carbazol-1(2H)-on 生成 1-chloro-5-methyl-9-methoxy-6H-pyrido<4,3-b>carbazole
  参考文献：
  名称：

  RIVALLE, C.;WENDLING, F.;TAMBOURIN, P.;LHOSTE, J. -M.;BISAGNI, E.;CHERMAN+, J. MED. CHEM., 1983, 26, N 2, 181-185

  摘要：

  DOI：

文献信息

• Antitumor amino-substituted pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinolines and pyrido[4,3-b]carbazole derivatives: synthesis and evaluation of compounds resulting from new side chain and heterocycle modifications
  作者：Christian Rivalle、Francoise Wendling、Pierre Tambourin、Jean Marc Lhoste、Emile Bisagni、Jean Claude Chermann

  DOI：10.1021/jm00356a012

  日期：1983.2

  11-dimethyl-6H-pyrido[4,3-b]carba zole (4b), which display important antitumor properties, were performed either on the side chain or on the intercalating heterocycle. Side chains were introduced by direct substitution of the corresponding chloro derivatives and 6-N-methyl-9-hydroxypyrido[4,3-b]carbazoles analogues were prepared via 9-O-benzoyl-1-chloroellipticines. Evaluation of all new compounds shows no significant

  10-[[[3-（二乙基氨基）丙基]氨基] -6-甲基-5H-吡啶基[3'，4'：4,5]吡咯并[2,3-g] i异喹啉（1b）和1的新修饰对[[[3-（二乙基氨基）丙基]氨基] -9-甲氧基-5,11-二甲基-6H-吡啶基[4,3-b]卡巴唑（4b）进行了重要的抗肿瘤研究，侧链或插入杂环上。通过直接取代相应的氯衍生物引入侧链，并通过9-O-苯甲酰基-1-氯玫瑰树碱制备6-N-甲基-9-羟基吡啶并[4,3-b]咔唑类似物。与模型化合物1b和4b相比，对所有新化合物的评估均显示L1210白血病系统的体外细胞毒性和ILS百分比没有显着增加。
• Structure-activity relationship in a series of newly synthesized 1-amino-substituted ellipticine derivatives
  作者：Claire Ducrocq、Francoise Wendling、Jean Claude Chermann、Martine Tourbez-Perrin、Christian Rivalle、Pierre Tambourin、Francois Pochon、Emile Bisagni

  DOI：10.1021/jm00185a012

  日期：1980.11

  corresponding 9-methoxylated compounds. However, their antitumor efficiencies on the in vivo experimental systems do not confirm the advantage of demethylation. The presence of a [(dialkylamino)alkyl]amino side chain at the 1 position of ellipticines increases the antitumor potency: 1-[[3-(diethylamino)propyl]amino]-5,11-dimethyl-6H-pyrido[4,3-b]carbazole (5) is a very potent antitumor compound (% ILS of 134 on

  据报道，基于相应的1-氯玫瑰树碱的取代，合成了一系列1-氨基取代的吡啶并[4,3-b]咔唑衍生物。描述了对体外生长的肿瘤细胞的细胞毒性特性，最有效的体外细胞毒性化合物的体内急性毒性以及对L1210白血病系统的抗肿瘤特性。在该系列中，未观察到与DNA的明显缔合常数与体外细胞毒性或体外抗肿瘤效率之间的相关性。9-羟基化衍生物在体外比相应的9-甲氧基化化合物更具细胞毒性。然而，它们在体内实验系统上的抗肿瘤效率并未证实去甲基化的优势。
• Use of indole-derived compounds for the preparation of a medicament that can be used to treat diseases related to the splicing process
  申请人：Tazi Jamal

  公开号：US20070054905A1

  公开（公告）日：2007-03-08

  The invention relates to indole-derived compounds and to the use of said compounds for the preparation of a medicament that can be used to treat diseases related to the process of splicing pre-messenger RNAs in the cell, such as Frasier syndrome, frontotemporal dementia linked to chromonsoem 17 (a form of Parkinson's disease), Leigh syndrome (a type of encephalopathy), atypical cystic fibrosis, certain neuropathologies including Alzheimer's disease linked to a mutation in the Tau protein, muscle atorphy which affects the SMN (survival of Motor Neuron) gene, depression linked to a serotonin splicing impairment, and certain cancers in which the global splicing process is affected (e.g. breast cancer, colon cancer and certain lymphomas), as well as viral diseases such as AIDS.

  该发明涉及吲哚衍生物化合物及其用于制备药物的用途，该药物可用于治疗与细胞内预信使RNA剪接过程相关的疾病，如弗雷泽综合征、与染色体17相关的额颞叶痴呆症（一种帕金森病形式）、利综合征（一种脑病类型）、非典型囊性纤维化、某些神经病理学疾病，包括与Tau蛋白突变相关的阿尔茨海默病、影响SMN（运动神经元存活）基因的肌肉萎缩、与血清素剪接障碍相关的抑郁症，以及全局剪接过程受影响的某些癌症（例如乳腺癌、结肠癌和某些淋巴瘤），以及病毒性疾病，如艾滋病。
• PYRIDOCARBAZOLE TYPE COMPOUNDS AND APPLICATIONS THEREOF
  申请人：Lafanechere Laurence

  公开号：US20120041017A1

  公开（公告）日：2012-02-16

  Pyridocarbazole-type compounds of formula (I): are provided as a medicament, and more particularly for application in anticancer chemotherapy. Also provided is a pharmaceutical composition with the compound and methods for preventing and/or treating neurodegenerative-type pathologies, such as Alzheimer's disease and schizophrenia, parasitoses, such as malaria, or glaucomas.

  提供了化学式（I）的吡啶咔唑类化合物作为药物，特别是用于抗癌化疗的应用。还提供了含有该化合物的制药组合物以及预防和/或治疗神经退行性疾病类型，如阿尔茨海默病和精神分裂症，寄生虫病，如疟疾，或青光眼的方法。
• Pyridocarbazole type compounds and applications thereof
  申请人：Lafanechere Laurence

  公开号：US08604048B2

  公开（公告）日：2013-12-10

  Pyridocarbazole-type compounds of formula (I): are provided as a medicament, and more particularly for application in anticancer chemotherapy. Also provided is a pharmaceutical composition with the compound and methods for preventing and/or treating neurodegenerative-type pathologies, such as Alzheimer's disease and schizophrenia, parasitoses, such as malaria, or glaucomas.

  提供一种化合物，其为公式（I）所示的吡啶并[3,4]咔唑型化合物，作为药物，特别是用于抗癌化疗的应用。还提供了含有该化合物的制药组合物以及预防和/或治疗神经退行性病理，如阿尔茨海默病和精神分裂症，寄生虫病，如疟疾，或青光眼的方法。