4-amino-3-methyl-isothiazole-5-carbonitrile | 4592-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-3-methyl-isothiazole-5-carbonitrile
• 英文别名: 4-Amino-5-cyano-3-methyl-isothiazol；5-Isothiazolecarbonitrile, 4-amino-3-methyl-；4-amino-3-methyl-1,2-thiazole-5-carbonitrile
• CAS: 4592-55-6
• 化学式: C₅H₅N₃S
• mdl: MFCD19206070
• 分子量: 139.181
• InChiKey: XZDZUCRODSLLGD-UHFFFAOYSA-N

物化性质

• 沸点：
  203.7±40.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-环戊氧基-4-甲基苯甲酰氯 、 4-amino-3-methyl-isothiazole-5-carbonitrile 生成 N-(5-cyano-3-methylisothiazol-4-yl)-3-cyclopentyloxy-4-methoxybenzamide
  参考文献：
  名称：

  Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs

  摘要：

  The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described. The effects of changes to the alkoxy groups, amide linkage, and benzamide N-phenyl ring on the inhibition of the cytosolic PDE IV from pig aorta have been investigated. As a result, some highly potent and selective PDE IV inhibitors have been identified. The most potent compounds have been further evaluated for their inhibitory potencies against PDE IV obtained from and superoxide O-2(-) generation from guinea pig eosinophils in vitro. Selected compounds have also been examined for their activities in inhibiting histamine-induced bronchospasm in anaesthetized guinea pigs. 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide (15j) showed exceptional potency in all tests and may have therapeutic potential in the treatment of asthma.

  DOI：

  10.1021/jm00037a021
• 作为产物：
  描述：

  5-cyano-3-methyl-4-nitroisothiazole 在 platinum on activated charcoal 氢气 作用下， 以 水 为溶剂， 生成 4-amino-3-methyl-isothiazole-5-carbonitrile
  参考文献：
  名称：

  1337.异噻唑。第九部分 异噻唑并嘧啶

  摘要：

  DOI：

  10.1039/jr9650007277