diethyl 4-(5-hydroxybenzo[d] thiazol-2-yl)benzylphosphonate | 101078-70-0

• 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: diethyl 4-(5-hydroxybenzo[d] thiazol-2-yl)benzylphosphonate
• 英文别名: 2-[4-(Diethoxyphosphorylmethyl)phenyl]-1,3-benzothiazol-6-ol
• CAS: 101078-70-0
• 化学式: C₁₈H₂₀NO₄PS
• 分子量: 377.401
• InChiKey: LIJYVVCKNXKBCN-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  559.1±60.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 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：
  96.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-(5-hydroxybenzo[d] thiazol-2-yl)benzylphosphonate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (E)-1-fluoro-3-((2-(4-(4-(methylamino)styryl)phenyl)benzo[d]thiazol-6-yl)oxy)propan-2-ol
  参考文献：
  名称：

  타우 응집체에 높은 선택성을 가지는 화합물, 이를 포함하는 타우 표적 프로브, 및 이의 제조 방법

  摘要：

  本发明涉及一种被表示为化学式1的化合物，该化合物展现出对τ蛋白聚集体具有优异的结合力，可用于早期诊断、预防和治疗包括痴呆在内的退行性脑疾病，以及涉及制备方法和包含该化合物的药学配方。

  公开号：

  KR20190139189A
• 作为产物：
  描述：

  6-甲氧基-2-(对甲苯基)苯并[D]噻唑 在 氢氧化钾 、 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 、 乙醇 为溶剂， 反应 21.75h， 生成 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

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.
• 타우 응집체에 높은 선택성을 가지는 화합물, 이를 포함하는 타우 표적 프로브, 및 이의 제조 방법
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR20190139189A

  公开（公告）日：2019-12-17

  본 발명은 타우 응집체에 우수한 결합력을 나타내어 치매를 포함한 퇴행성 뇌질환의 조기 진단과, 이의 예방 및 치료에 유용한 하기 화학식 1로 표시되는 화합물, 이의 제조 방법 및 이를 포함하는 약학적 조성물에 관한 것이다.

  本发明涉及一种被表示为化学式1的化合物，该化合物展现出对τ蛋白聚集体具有优异的结合力，可用于早期诊断、预防和治疗包括痴呆在内的退行性脑疾病，以及涉及制备方法和包含该化合物的药学配方。