(2'Z)-7-azaindirubin | 1202876-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (2'Z)-7-azaindirubin
• 英文别名: (3Z)-3-(3-oxo-1H-indol-2-ylidene)-1H-pyrrolo[2,3-b]pyridin-2-one
• CAS: 1202876-70-7
• 化学式: C₁₅H₉N₃O₂
• 分子量: 263.255
• InChiKey: YIRSIXXVSDFDIN-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.09
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2'Z)-7-azaindirubin 在 吡啶 、 盐酸羟胺 作用下， 反应 24.0h， 以95%的产率得到(2'Z,3'E)-7-azaindirubin-3'-oxime
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of 7-Azaindirubin-3′-oxime, a 7-Aza Isostere of the Natural Indirubin Pharmacophore

  摘要：

  The bis-indole alkaloid indirubin and its analogues bear a very interesting natural pharmacophore. They are recognized mainly as kinase inhibitors, but several other activities make them possible candidates for preclinical studies. Based on the previously reported activity of 7-bromoindirubin-3'-oxime and its derivatives, the synthesis of indirubins bearing a heterocyclic nitrogen atom at position 7 was carried out. Herein, we report the first synthesis of 7-azaindirubin-3'-oxime (12) as well as its antiproliferative activity against 57 cancer cell lines and its inhibitory activity against a series of kinases. 7-Azaindirubin (10) and its 3'-oxime derivative (12) showed reduced activity as kinase inhibitors in comparison with other known indirubin derivatives, but antiproliferative activity with a best GI(50) value of 0.77 mu M.

  DOI：

  10.1021/np9003905
• 作为产物：
  描述：

  1H-吡咯[2,3-B]吡啶-2,3-二酮 、 吲哚乙酸酯 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.08h， 以73%的产率得到(2'Z)-7-azaindirubin
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of 7-Azaindirubin-3′-oxime, a 7-Aza Isostere of the Natural Indirubin Pharmacophore

  摘要：

  The bis-indole alkaloid indirubin and its analogues bear a very interesting natural pharmacophore. They are recognized mainly as kinase inhibitors, but several other activities make them possible candidates for preclinical studies. Based on the previously reported activity of 7-bromoindirubin-3'-oxime and its derivatives, the synthesis of indirubins bearing a heterocyclic nitrogen atom at position 7 was carried out. Herein, we report the first synthesis of 7-azaindirubin-3'-oxime (12) as well as its antiproliferative activity against 57 cancer cell lines and its inhibitory activity against a series of kinases. 7-Azaindirubin (10) and its 3'-oxime derivative (12) showed reduced activity as kinase inhibitors in comparison with other known indirubin derivatives, but antiproliferative activity with a best GI(50) value of 0.77 mu M.

  DOI：

  10.1021/np9003905

文献信息

• Conjugate of Benzofuranone and Indole or Azaindole, and Preparation and Uses Thereof
  申请人：LUODA BIOSCIENCES, INC.

  公开号：US20160185771A1

  公开（公告）日：2016-06-30

  The present invention relates to an oxo indirubin or isoindigo derivative, an oxo aza indirubin or isoindigo derivative, and their optical isomers, racemes, cis/trans isomers and pharmaceutically acceptable salts, which can be used for preparing a drug for treating or preventing diseases such as glucose metabolic disorder, inflammatory or autoimmune disease, neurodegenerative disease, a mental illness, tissue proliferation disease or tumors.

  本发明涉及一种酮基吲哚蓝或异靛蓝衍生物，一种酮基氮杂吲哚蓝或异靛蓝衍生物，以及它们的光学异构体、消旋体、顺反异构体和药学上可接受的盐，可用于制备治疗或预防葡萄糖代谢紊乱、炎症或自身免疫疾病、神经退行性疾病、精神疾病、组织增生疾病或肿瘤等疾病的药物。
• Indirubin derivatives, and uses thereof
  申请人：CITY OF HOPE

  公开号：US11524937B2

  公开（公告）日：2022-12-13

  Indirubin is the major active anti-tumor component of a traditional Chinese herbal medicine used for treatment of chronic myelogenous leukemia (CML). Indirubin derivatives (IRDs) potently reduce the viabilities of various cancer cells and affect kinase activities. IRDs disclosed herein provide new therapeutics for cancer and conditions regulated by the kinase activities.

  靛红素是一种用于治疗慢性骨髓性白血病（CML）的传统中药的主要抗肿瘤活性成分。靛红衍生物（IRDs）能有效降低各种癌细胞的存活率并影响激酶活性。本文公开的 IRDs 为癌症和受激酶活性调节的疾病提供了新的治疗方法。
• [EN] CONJUGATE OF BENZOFURANONE AND INDOLE OR AZAINDOLE, AND PREPARATION AND USES THEREOF<br/>[FR] CONJUGUÉ DE BENZOFURANONE ET D'INDOLE OU D'AZA-INDOLE ET LEUR PRÉPARATION ET LEURS UTILISATIONS
  申请人：LUODA BIOSCIENCES INC

  公开号：WO2014190758A1

  公开（公告）日：2014-12-04

  本申请公开了一种氧代靛玉红或异靛蓝衍生物、以及氧代氮杂靛玉红或异靛蓝的衍生物，以及其光学异构体、外消旋体、顺反异构体和药学上可接受的盐，其可以用于制备预防或治疗如糖代谢紊乱、炎性和自身免疫性疾病、神经退化性疾病、精神性疾病、组织增生性疾病或肿瘤等疾病的药物。
• INDIRUBIN DERIVATIVES, AND USES THEREOF
  申请人：CITY OF HOPE

  公开号：US20200247750A1

  公开（公告）日：2020-08-06

  Indirubin is the major active anti-tumor component of a traditional Chinese herbal medicine used for treatment of chronic myelogenous leukemia (CML). Indirubin derivatives (IRDs) potently reduce the viabilities of various cancer cells and affect kinase activities. IRDs disclosed herein provide new therapeutics for cancer and conditions regulated by the kinase activities.
• US9868734B2
  申请人：——

  公开号：US9868734B2

  公开（公告）日：2018-01-16