β-Chlor-isopropylisocyanat | 10146-79-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: β-Chlor-isopropylisocyanat
• 英文别名: 1-Chlor-2-isocyanato-propan；1-Chlormethyl-1-isocyanato-ethan；1-Chlormethyl-ethylisocyanat；β-chloro-isopropyl isocyanate；beta-Chloro-isopropyl isocyanate；1-chloro-2-isocyanatopropane
• CAS: 10146-79-9
• 化学式: C₄H₆ClNO
• mdl: MFCD19232140
• 分子量: 119.551
• InChiKey: SVMHBOVTFNUJNI-UHFFFAOYSA-N

物化性质

• 沸点：
  141-142 °C
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-Chlor-isopropylisocyanat 、 2-氯-6-肼基吡啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(1-Chloropropan-2-yl)-3-[(6-chloropyridin-2-yl)amino]urea
  参考文献：
  名称：

  5-Lipoxygenase Inhibitors:  Synthesis and Structure−Activity Relationships of a Series of 1-Aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones

  摘要：

  Synthetic routes were developed to access a variety of novel 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-one analogs which were evaluated as 5-lipoxygenase (5-LO) inhibitors. The parent structure, 1-phenylperhydro-1,2,4-triazin-3-one (4), was found to be a selective inhibitor of 5-LO in broken cell, intact cell, and human blood assays with IC50 values of 5-21 mu M. In a rat anaphylaxis model, 4 blocked leukotriene formation with an ED(50) = 7 mg/kg when administered orally. Compound 4 exhibited selectivity for inhibition of 5-LO with little activity against related enzymes: 12-LO from human platelets, 15-LO from soybean, and cyclooxygenase (COX) from sheep seminal vesicle. In pilot subacute toxicity testing, 4 did not produce methemoglobinemia in rats (400 mg/kg po daily for 9 days) or in dogs (200 mg/kg po daily for 28 days). These results indicated that the triazinone structure provided a 5-LO inhibitor template devoid of the toxicity problems observed in the related phenidone (1) and pyridazinone (3) classes of 5-LO inhibitors. The parent compound 4 is a selective, orally bioavailable 5-LO inhibitor which can serve as a useful reference standard for in vivo pharmacological studies involving leukotriene-mediated phenonmena.

  DOI：

  10.1021/jm960372b
• 作为产物：
  描述：

  2-Dichlormethylenamino-1-chlor-propan 在 水 、 三氯氧磷 作用下， 生成 β-Chlor-isopropylisocyanat
  参考文献：
  名称：

  Neue präparative Wege zu Kohlensäureimid-Derivaten

  摘要：

  DOI：

  10.1055/s-1970-21576

文献信息

• Najer et al., Bulletin de la Societe Chimique de France, 1959, p. 1611,1614
  作者：Najer et al.

  DOI：——

  日期：——
• Najer,H. et al., Bulletin de la Societe Chimique de France, 1960, p. 1544 - 1548
  作者：Najer,H. et al.

  DOI：——

  日期：——
• Kampe,K.-D., Justus Liebigs Annalen der Chemie, 1971, vol. 752, p. 142 - 162
  作者：Kampe,K.-D.

  DOI：——

  日期：——
• MULLER, KLAUS-HELMUT;KLUTH, JOACHIM;KONIG, KLAUS;GASSEN, KARL-RUDOLF;FIND+
  作者：MULLER, KLAUS-HELMUT、KLUTH, JOACHIM、KONIG, KLAUS、GASSEN, KARL-RUDOLF、FIND+

  DOI：——

  日期：——
• 5-Lipoxygenase Inhibitors:  Synthesis and Structure−Activity Relationships of a Series of 1-Aryl-2<i>H</i>,4<i>H</i>-tetrahydro-1,2,4-triazin-3-ones
  作者：Pramila A. Bhatia、Clint D. W. Brooks、Anwer Basha、James D. Ratajczyk、Bruce P. Gunn、Jennifer B. Bouska、Carmine Lanni、Patrick R. Young、Randy L. Bell、George W. Carter

  DOI：10.1021/jm960372b

  日期：1996.1.1

  Synthetic routes were developed to access a variety of novel 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-one analogs which were evaluated as 5-lipoxygenase (5-LO) inhibitors. The parent structure, 1-phenylperhydro-1,2,4-triazin-3-one (4), was found to be a selective inhibitor of 5-LO in broken cell, intact cell, and human blood assays with IC50 values of 5-21 mu M. In a rat anaphylaxis model, 4 blocked leukotriene formation with an ED(50) = 7 mg/kg when administered orally. Compound 4 exhibited selectivity for inhibition of 5-LO with little activity against related enzymes: 12-LO from human platelets, 15-LO from soybean, and cyclooxygenase (COX) from sheep seminal vesicle. In pilot subacute toxicity testing, 4 did not produce methemoglobinemia in rats (400 mg/kg po daily for 9 days) or in dogs (200 mg/kg po daily for 28 days). These results indicated that the triazinone structure provided a 5-LO inhibitor template devoid of the toxicity problems observed in the related phenidone (1) and pyridazinone (3) classes of 5-LO inhibitors. The parent compound 4 is a selective, orally bioavailable 5-LO inhibitor which can serve as a useful reference standard for in vivo pharmacological studies involving leukotriene-mediated phenonmena.