(E)-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile | 726208-00-0

• 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: (E)-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile
• 英文别名: (3-Oxo-1,3-dihydroindol-2-ylidene) phenylacetonitrile；(2E)-2-(3-oxo-1H-indol-2-ylidene)-2-phenylacetonitrile
• CAS: 726208-00-0
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: KMXPWAQWOVKAIV-SQFISAMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 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：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile 在 sodium ethanolate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 5-Ethyl-4-phenyl-pyridazino[4,3-b]indol-3-amine
  参考文献：
  名称：

  Novel Pyridazino[4,3-b]indoles with Dual Inhibitory Activity against Mycobacterium tuberculosis and Monoamine Oxidase

  摘要：

  Tuberculosis is one of the most common infectious diseases known to man. About 37% of the world's population (about 1.86 billion people) are infected with Mycobacterium tuberculosis. According to the World Health Organization, every year approximately 8 million people develop active tuberculosis and almost 2 million of those die from the disease. The incidence of multidrug-resistant tuberculosis (MDR-TB) is increasing. The present drug regimen for treating tuberculosis has been in existence for 30 years. New drugs that will shorten total treatment duration, improve the treatment of MDR-TB, and address latent tuberculosis are the most urgent need of tuberculosis control programs. A new series of synthetic 3-amino-4-arylpyridazino[4,3-b]indoles (pyridazinoindoles) were identified as inhibitors of Mycobacterium tuberculosis. The design, synthesis, and antimycobacterial activity of these compounds are described. While the most active compounds are still not comparable to the front-line drugs rifampicin and isoniazid, they do show promise. Most of the pyridazinoindoles with appreciable antituberculosis activity also inhibit monoamine oxidase, suggestive of a novel inhibitory effect on mycobacterial redox reactions.

  DOI：

  10.1021/jm030479g
• 作为产物：
  描述：

  邻硝基苯乙酮 在 水 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成 (E)-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile
  参考文献：
  名称：

  邻硝基查尔酮意外环化为 2-亚烷基吲哚啉-3-酮

  摘要：

  描述了一种从邻硝基查耳酮制备 2-(3-oxindolin-2-ylidene) 乙腈的原始、简便且高效的方法。特征转化是氰化物阴离子触发的迈克尔加成到查尔酮，然后是与 Baeyer-Drewson 反应机制相关的级联环化。

  DOI：

  10.1039/d0ra03520c

文献信息

• One-Pot Synthesis of (E)-2-(3-Oxoindolin-2-ylidene)-2-arylacetonitriles
  作者：Nicolai A. Aksenov、Alexander V. Aksenov、Igor A. Kurenkov、Nikita K. Kirillov、Dmitrii A. Aksenov、Nikolai A. Arutiunov、Daria S. Aksenova、Michael Rubin

  DOI：10.3390/molecules27092808

  日期：——

  A highly efficient and expeditious one-pot approach towards 2-(3-oxoindolin-2-yl)acetonitriles was designed, which involves a base-assisted aldol reaction of ortho-nitroacetophenones, followed by hydrocyanation, triggering an unusual reductive cyclization reaction.

  设计出了一种高效、快速的 2-(3-氧代吲哚啉-2-基)乙腈一锅法，该方法涉及邻硝基苯乙酮的碱辅助醛醇反应，然后进行氢氰酸化，引发不寻常的还原环化反应。
• Unexpected cyclization of <i>ortho</i>-nitrochalcones into 2-alkylideneindolin-3-ones
  作者：Nicolai A. Aksenov、Dmitrii A. Aksenov、Nikolai A. Arutiunov、Daria S. Aksenova、Alexander V. Aksenov、Michael Rubin

  DOI：10.1039/d0ra03520c

  日期：——

  An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from ortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically related to the Baeyer–Drewson reaction.

  描述了一种从邻硝基查耳酮制备 2-(3-oxindolin-2-ylidene) 乙腈的原始、简便且高效的方法。特征转化是氰化物阴离子触发的迈克尔加成到查尔酮，然后是与 Baeyer-Drewson 反应机制相关的级联环化。
• Novel Pyridazino[4,3-<i>b</i>]indoles with Dual Inhibitory Activity against <i>Mycobacterium </i><i>t</i><i>uberculosis</i> and Monoamine Oxidase
  作者：Valeriya S. Velezheva、Patrick J. Brennan、Vladimir Yu. Marshakov、Dmitrij V. Gusev、Inessa N. Lisichkina、Alexander S. Peregudov、Larisa N. Tchernousova、Tatiana G. Smirnova、Sofia N. Andreevskaya、Alexei E. Medvedev

  DOI：10.1021/jm030479g

  日期：2004.6.1

  Tuberculosis is one of the most common infectious diseases known to man. About 37% of the world's population (about 1.86 billion people) are infected with Mycobacterium tuberculosis. According to the World Health Organization, every year approximately 8 million people develop active tuberculosis and almost 2 million of those die from the disease. The incidence of multidrug-resistant tuberculosis (MDR-TB) is increasing. The present drug regimen for treating tuberculosis has been in existence for 30 years. New drugs that will shorten total treatment duration, improve the treatment of MDR-TB, and address latent tuberculosis are the most urgent need of tuberculosis control programs. A new series of synthetic 3-amino-4-arylpyridazino[4,3-b]indoles (pyridazinoindoles) were identified as inhibitors of Mycobacterium tuberculosis. The design, synthesis, and antimycobacterial activity of these compounds are described. While the most active compounds are still not comparable to the front-line drugs rifampicin and isoniazid, they do show promise. Most of the pyridazinoindoles with appreciable antituberculosis activity also inhibit monoamine oxidase, suggestive of a novel inhibitory effect on mycobacterial redox reactions.