[5-Bromo-3-oxo-1,3-dihydro-indol-(2E)-ylidene]-(4-isopropyl-phenyl)-acetonitrile | 726208-10-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [5-Bromo-3-oxo-1,3-dihydro-indol-(2E)-ylidene]-(4-isopropyl-phenyl)-acetonitrile
• CAS: 726208-10-2
• 化学式: C₁₉H₁₅BrN₂O
• 分子量: 367.245
• InChiKey: ZBOALTISVVJNAP-VLGSPTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.89
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [5-Bromo-3-oxo-1,3-dihydro-indol-(2E)-ylidene]-(4-isopropyl-phenyl)-acetonitrile 在 一水合肼 、 溶剂黄146 作用下， 反应 5.0h， 生成 8-bromo-4-(4-isopropylphenyl)-5H-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：

  氰化钾 、 以 二甲基亚砜 为溶剂， 以75%的产率得到[5-Bromo-3-oxo-1,3-dihydro-indol-(2E)-ylidene]-(4-isopropyl-phenyl)-acetonitrile
  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