(3-nitrophenyl)-(9H-pyrido[2,3-b]indol-4-yl)amine | 1214220-18-4

• 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: (3-nitrophenyl)-(9H-pyrido[2,3-b]indol-4-yl)amine
• 英文别名: N-(3-nitrophenyl)-9H-pyrido[2,3-b]indol-4-amine
• CAS: 1214220-18-4
• 化学式: C₁₇H₁₂N₄O₂
• 分子量: 304.308
• InChiKey: NSTVFNSHCSHEMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9H-吡啶并[2,3-B]吲哚 在 双氧水 、 溶剂黄146 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 (3-nitrophenyl)-(9H-pyrido[2,3-b]indol-4-yl)amine
  参考文献：
  名称：

  Discovery of 4-anilino α-carbolines as novel Brk inhibitors

  摘要：

  Dysregulation of cell signalling processes caused by an enhanced activity of protein kinases mainly contributes to cancer progression. Protein kinase inhibitors have been established as promising drugs that inhibit such overactive protein kinases in cancer cells. The formation of metastases, which makes a therapy difficult, remains a great challenge for cancer treatment. Recently, breast tumor kinase (Brk) was discovered as novel and interesting target for a cancer therapy because Brk participates in both cell dysregulation and metastasis. We discovered 4-anilino substituted a-carboline compounds as a novel class of highly active Brk inhibitors. In the current work, structure-activity relationships are discussed including docking results obtained for 4-anilino alpha-carbolines. A first profiling of selective kinase inhibition and a proof of concept for the antiproliferative effects is demonstrated. These results qualify the compounds as a promising class of novel antitumor agents. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.002

文献信息

• Alpha-carboline inhibitors of NMP-ALK, RET, and Bcr-Abl
  申请人：Università Degli Studi Di Milano - Bicocca

  公开号：EP2161271A1

  公开（公告）日：2010-03-10

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in the description, to their pharmaceutical compositions and use thereof for the treatment of cancer expressing oncogenic ALK protein, particularly anaplastic large cell lymphoma (ALCL), diffuse large B cell lymphoma (DLBCL), inflammatory myofibroblastic tumours (IMT) and non-small cell lung cancer (NSCLC).

  本发明涉及式(I)的化合物，其中R1、R2和R3如描述中所定义，以及它们的药物组合物及其在治疗表达癌基因ALK蛋白的癌症，特别是间变性大细胞淋巴瘤(ALCL)、弥漫性大B细胞淋巴瘤(DLBCL)、炎性肌纤维母细胞瘤(IMT)和非小细胞肺癌(NSCLC)中的用途。
• Synthesis of 2-, 3-, and 4-Substituted Pyrido[2,3-b]indoles by C-N, C-O, and C-C(sp) Bond Formation
  作者：Cédric Schneider、David Goyard、David Gueyrard、Benoît Joseph、Peter G. Goekjian

  DOI：10.1002/ejoc.201000795

  日期：2010.12

  The synthesis of 2-, 3-, and 4-substituted alpha-carbolines is described starting from the corresponding chloropyrido[2,3-b]-indoles by Buchwald-Hartwig and Sonogashira cross-coupling reactions. Regioselective Sonogashira reactions on 2,4-dichloropyrido[2,3-b]indoles are also presented as an efficient route to unsymmetrically 2,4-disubstituted alpha-carbolines.

  通过 Buchwald-Hartwig 和 Sonogashira 交叉偶联反应，从相应的氯吡啶并 [2,3-b]-吲哚开始合成 2-、3-和 4-取代的 α-咔啉。2,4-二氯吡啶并 [2,3-b] 吲哚上的区域选择性 Sonogashira 反应也被认为是不对称 2,4-二取代 α-咔啉的有效途径。
• ALFA-CARBOLINE INHIBITORS OF NPM-ALK, RET, AND BCR-ABL
  申请人：Gambacorti Passerini Carlo

  公开号：US20110281862A1

  公开（公告）日：2011-11-17

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in the description, to their pharmaceutical compositions and use thereof for the treatment of cancer expressing oncogenic ALK protein, particularly anaplastic large cell lymphoma (ALCL), diffuse large B cell lymphoma (DLBCL), inflammatory myofibroblastic tumours (IMT) and non-small cell lung cancer (NSCLC).

  本发明涉及式（I）的化合物，其中R1，R2和R3如描述中所定义，以及它们的制药组合物和用于治疗表达癌基因ALK蛋白的癌症的用途，特别是间变性大细胞淋巴瘤（ALCL），弥漫性大B细胞淋巴瘤（DLBCL），炎性肌成纤维细胞瘤（IMT）和非小细胞肺癌（NSCLC）。
• US8895744B2
  申请人：——

  公开号：US8895744B2

  公开（公告）日：2014-11-25
• [EN] ALFA-CARBOLINE INHIBITORS OF NPM-ALK, RET, AND BCR-ABL<br/>[FR] INHIBITEURS DE NPM-ALK, RET, ET BCR-ABL À BASE D'ALPHA-CARBOLINE
  申请人：UNIV MILANO BICOCCA

  公开号：WO2010025872A2

  公开（公告）日：2010-03-11

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in the description, to their pharmaceutical compositions and use thereof for the treatment of cancer expressing oncogenic ALK protein, particularly anaplastic large cell lymphoma (ALCL), diffuse large B cell lymphoma (DLBCL), inflammatory myofibroblastic tumours (IMT) and non-small cell lung cancer (NSCLC).