4-(6-硝基苯并噻唑-2-基)苄基膦酸二乙酯 | 101078-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 4-(6-硝基苯并噻唑-2-基)苄基膦酸二乙酯
• 英文名称: diethyl 4-(6-nitrobenzothiazol-2-yl)benzylphosphonate
• 英文别名: 2-[4-(Diethoxyphosphorylmethyl)phenyl]-6-nitro-1,3-benzothiazole
• CAS: 101078-63-1
• 化学式: C₁₈H₁₉N₂O₅PS
• 分子量: 406.399
• InChiKey: NCLBIQNVHPPDQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(6-硝基苯并噻唑-2-基)苄基膦酸二乙酯 在 盐酸 、 tin 作用下， 反应 1.33h， 生成 diethyl 4-<6-(acetylamino)benzothiazol-2-yl>benzylphosphonate
  参考文献：
  名称：

  Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator

  摘要：

  A series of 4-(benzothiazol-2-yl)benzylphosphonic acid dialkyl ester derivatives were synthesized and evaluated for coronary vasodilatory activity by Langendorff's method in the isolated guinea pig heart. Many of the phosphonic acid dialkyl esters exhibited vasodilatory activity and calcium antagonism comparable with those of diltiazem hydrochloride, whereas phosphonic acid 1b and its nonphosphonated precursor 7a were inactive. These results indicate the necessity of the diethoxyphosphinyl moiety for vasodilatory activity. Substitution of the benzothiazole ring with a variety of substituents did not significantly enhance the activity of the unsubstituted compound. Compound 10b (KB-944) was chosen for detailed pharmacological evaluation.

  DOI：

  10.1021/jm00155a037
• 作为产物：
  描述：

  2-(4-溴甲基苯基)苯并噻唑 在 硫酸 、 硝酸 作用下， 反应 1.25h， 生成 4-(6-硝基苯并噻唑-2-基)苄基膦酸二乙酯
  参考文献：
  名称：

  Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator

  摘要：

  A series of 4-(benzothiazol-2-yl)benzylphosphonic acid dialkyl ester derivatives were synthesized and evaluated for coronary vasodilatory activity by Langendorff's method in the isolated guinea pig heart. Many of the phosphonic acid dialkyl esters exhibited vasodilatory activity and calcium antagonism comparable with those of diltiazem hydrochloride, whereas phosphonic acid 1b and its nonphosphonated precursor 7a were inactive. These results indicate the necessity of the diethoxyphosphinyl moiety for vasodilatory activity. Substitution of the benzothiazole ring with a variety of substituents did not significantly enhance the activity of the unsubstituted compound. Compound 10b (KB-944) was chosen for detailed pharmacological evaluation.

  DOI：

  10.1021/jm00155a037

文献信息

• YOSHINO, KOHICHIRO;KOHNO, TOSHIHIKO;UNO, TOSHIO;TOMINORI, MORITA;TSUKAMOT+, J. MED. CHEM., 1986, 29, N 5, 820-825
  作者：YOSHINO, KOHICHIRO、KOHNO, TOSHIHIKO、UNO, TOSHIO、TOMINORI, MORITA、TSUKAMOT+

  DOI：——

  日期：——