3-aminomethylene-indolin-2-one | 64757-79-5

• 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-aminomethylene-indolin-2-one
• 英文别名: 3-Aminomethylen-indolin-2-on；(3Z)-3-(aminomethylidene)-1H-indol-2-one
• CAS: 64757-79-5
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: TWNBFBFTWZXLAG-ALCCZGGFSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  390.1±42.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-aminomethylene-indolin-2-one 在 吡啶 、 palladium on activated charcoal 、 乙醇 作用下， 生成 N-(2-oxo-indolin-3-ylmethyl)-acetamide
  参考文献：
  名称：

  3-Hydroxymethyleneoxindole and its Derivatives

  摘要：

  DOI：

  10.1021/ja01523a068
• 作为产物：
  描述：

  (Z)-3-chloromethylene-indolin-2-one 在 ammonium hydroxide 作用下， 以55%的产率得到3-aminomethylene-indolin-2-one
  参考文献：
  名称：

  Wasalexins A和B，来自芥末的新植物抗毒素：分离，合成和抗真菌活性。

  摘要：

  芥蓝（Wasabia japonica，同种Eutrema wasabi）中两种植物抗毒素的化学结构测定，芥蓝对黑腿真菌[Leptosphaeria maculans（Desm。）Ces。等人，无性阶段Phoma lingam（Tode ex Fr.）Desm。]，以及它们的合成和对P. lingam和山葵假单胞菌的分离物的抗真菌活性已有报道。

  DOI：

  10.1016/s0960-894x(99)00523-5

文献信息

• METHOD OF USING AN INDOLINONE MOLECULE AND DERIVATIVES FOR INHIBITING LIVER FIBROSIS AND HEPATITIS
  申请人：Acclaim BioMed USA LLC

  公开号：US20150045395A1

  公开（公告）日：2015-02-12

  This invention relates to methods of reversing and inhibiting liver fibrosis and hepatitis using a small indolinone molecule Hesperadin and related compounds. Methods of identifying such agents and using them to inhibit the expression of collagens and ECM proteins including MMPs and TIMPs in purified hepatic stellate cells are provided. In vivo data of Hesperadin in inhibiting induced collagen production are presented. This method of specifically targeting drugs to hepatic stellate cells in vivo, provides a novel therapy for liver diseases.

  本发明涉及使用小分子indolinone Hesperadin及其相关化合物来逆转和抑制肝纤维化和肝炎的方法。提供了识别这些药物并将它们用于抑制纯化肝星状细胞中胶原和ECM蛋白质表达（包括MMPs和TIMPs）的方法。介绍了Hesperadin在抑制诱导的胶原产生方面的体内数据。这种特异性靶向药物作用于肝星状细胞的方法，为治疗肝病提供了一种新的疗法。
• Method of using an indolinone molecule and derivatives for inhibiting liver fibrosis and hepatitis
  申请人：Acclaim BioMed USA LLC

  公开号：US10450295B2

  公开（公告）日：2019-10-22

  This invention relates to methods of reversing and inhibiting liver fibrosis and hepatitis using a small indolinone molecule Hesperadin and related compounds. Methods of identifying such agents and using them to inhibit the expression of collagens and ECM proteins including MMPs and TIMPs in purified hepatic stellate cells are provided. In vivo data of Hesperadin in inhibiting induced collagen production are presented. This method of specifically targeting drugs to hepatic stellate cells in vivo, provides a novel therapy for liver diseases.

  本发明涉及使用小吲哚啉酮分子 Hesperadin 和相关化合物逆转和抑制肝纤维化和肝炎的方法。本发明提供了鉴定此类制剂并使用它们抑制胶原和 ECM 蛋白（包括纯化肝星状细胞中的 MMPs 和 TIMPs）表达的方法。介绍了 Hesperadin 抑制诱导胶原蛋白生成的体内数据。这种在体内将药物特异性靶向肝星状细胞的方法为治疗肝病提供了一种新的疗法。
• Behringer; Weissauer, Chemische Berichte, 1952, vol. 85, p. 774,777
  作者：Behringer、Weissauer

  DOI：——

  日期：——
• Discovery of inhibitors of brassinin oxidase based on the scaffolds of the phytoalexins brassilexin and wasalexin
  作者：M. Soledade C. Pedras、Zoran Minic、Vijay K. Sarma-Mamillapalle、Mojmir Suchy

  DOI：10.1016/j.bmc.2010.02.054

  日期：2010.4

  Inhibitors of brassinin oxidase (BOLm), a unique phytoalexin detoxifying enzyme produced by the plant pathogenic fungus Leptosphaeria maculans (asexual stage Phoma lingam), were designed based on scaffolds of the phytoalexins brassilexin and wasalexin. Evaluation of these compounds using purified BOLm established that the inhibitory effect of brassilexin and derivatives decreased as follows: 6-chlorobrassilexin approximate to 6-bromobrassilexin > 5-bromobrassilexin approximate to 5-chlorobrassilexin approximate to 6-fluorobrassilexin > 8-methylbrassilexin > brassilexin approximate to 5-fluorobrassilexin. 6-Chlorobrassilexin was determined to be the best competitive inhibitor of BOLm discovered to date, with a K-i = 31 mu M. Importantly, brassilexin and derivatives did not appear to induce BOLm in fungal cultures. Overall, these results suggest that the brassilexin scaffold is a good lead for further development of paldoxins against L. maculans, as it inhibits competitively BOLm without apparent induction. (C) 2010 Elsevier Ltd. All rights reserved.
• US4145422A
  申请人：——

  公开号：US4145422A

  公开（公告）日：1979-03-20