[2-[4-(Diethoxyphosphorylmethyl)phenyl]-1,3-benzothiazol-6-yl] acetate | 101078-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: [2-[4-(Diethoxyphosphorylmethyl)phenyl]-1,3-benzothiazol-6-yl] acetate
• CAS: 101078-67-5
• 化学式: C₂₀H₂₂NO₅PS
• 分子量: 419.438
• InChiKey: YHULWHCHCXVCSV-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  569.2±60.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [2-[4-(Diethoxyphosphorylmethyl)phenyl]-1,3-benzothiazol-6-yl] acetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到diethyl 4-(5-hydroxybenzo[d] thiazol-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：

  6-甲氧基-2-(对甲苯基)苯并[D]噻唑 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氢溴酸 作用下， 以 四氯化碳 为溶剂， 反应 21.25h， 生成 [2-[4-(Diethoxyphosphorylmethyl)phenyl]-1,3-benzothiazol-6-yl] acetate
  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：——
• Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator
  作者：Kohichiro Yoshino、Toshihiko Kohno、Toshio Uno、Tominori Morita、Goro Tsukamoto

  DOI：10.1021/jm00155a037

  日期：1986.5

  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.