乙基[2-(4-氯苯基)-5-(2-呋喃基)-1,3-恶唑-4-基]乙酸酯 | 88352-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 乙基[2-(4-氯苯基)-5-(2-呋喃基)-1,3-恶唑-4-基]乙酸酯
• 中文别名: 2-萘磺酸,4-羟基-3-[[4-[(4-硝基-2-硫代苯基)偶氮]-6(或7)-硫代-1-萘基]偶氮]-7-(苯基氨基)-,盐(9CI)三钠
• 英文名称: TA-1801
• 英文别名: ethyl 2-[2-(4-chlorophenyl)-5-(furan-2-yl)-4-oxazolyl]acetate；ethyl 2-[2-(4-chlorophenyl)-5-(2-furyl)-4-oxazolyl]acetate；ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate；Ethyl 2-(4-chlorophenyl)-5-(2-furyl)oxazole-4-acetate；ethyl 2-[2-(4-chlorophenyl)-5-(furan-2-yl)-1,3-oxazol-4-yl]acetate
• CAS: 88352-44-7
• 化学式: C₁₇H₁₄ClNO₄
• 分子量: 331.755
• InChiKey: HUPJQAHXMFEKJY-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C(Solv: ethanol (64-17-5))
• 沸点：
  471.0±55.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  2-8℃

制备方法与用途

生物活性

TA-1801 是一种降血脂剂。

体外研究

TA-1801 能够抑制血小板聚集。

体内研究

在正常大鼠中，0.05% 剂量的 TA-1801 可使血清胆固醇和甘油三酯水平分别降低 23% 和 35%。而在遗传性高脂血症大鼠 (THLR/1) 中，TA-1801 的活性大约是正常大鼠的 10 倍。

反应信息

• 作为反应物：
  描述：

  乙基[2-(4-氯苯基)-5-(2-呋喃基)-1,3-恶唑-4-基]乙酸酯 在 硫酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以41%的产率得到ethyl 2-(4-chlorophenyl)-5-(5-sulfo-2-furyl)-4-oxazoleacetate
  参考文献：
  名称：

  Synthesis of ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate, a hypolipidemic agent, and related compounds

  摘要：

  A series of 2-aryl and 2-alkyl derivatives of 5-furyl-4-oxazoleacetic acid and their homologues having alkyl groups at the alpha-position of the acids were synthesized and evaluated for their hypolipidemic activities in Sprague-Dawley rats. On the basis of the structure-activity relationships and subacute toxicities, ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate (35) was selected as a candidate compound for development. Compound 35 reduced serum cholesterol and triglyceride levels by 23% and 35%, respectively, at a dose of 0.05% in a diet in normal rats, and it was about 10 times more active in hereditary hyperlipidemic rats (THLR/1) than in normal rats. Compound 35 inhibited platelet aggregation in vitro and also normalized hyperaggregability of hyperlipidemic plasma platelet ex vivo.

  DOI：

  10.1021/jm00401a021
• 作为产物：
  描述：

  4-氯苯甲酰氯 在 sodium hydride 、 碳酸氢钠 、 三氯氧磷 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 8.83h， 生成 乙基[2-(4-氯苯基)-5-(2-呋喃基)-1,3-恶唑-4-基]乙酸酯
  参考文献：
  名称：

  Synthesis of ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate, a hypolipidemic agent, and related compounds

  摘要：

  A series of 2-aryl and 2-alkyl derivatives of 5-furyl-4-oxazoleacetic acid and their homologues having alkyl groups at the alpha-position of the acids were synthesized and evaluated for their hypolipidemic activities in Sprague-Dawley rats. On the basis of the structure-activity relationships and subacute toxicities, ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate (35) was selected as a candidate compound for development. Compound 35 reduced serum cholesterol and triglyceride levels by 23% and 35%, respectively, at a dose of 0.05% in a diet in normal rats, and it was about 10 times more active in hereditary hyperlipidemic rats (THLR/1) than in normal rats. Compound 35 inhibited platelet aggregation in vitro and also normalized hyperaggregability of hyperlipidemic plasma platelet ex vivo.

  DOI：

  10.1021/jm00401a021

文献信息

• Furyloxazolylacetic acid derivatives and processes for preparing same
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04642313A1

  公开（公告）日：1987-02-10

  A furyloxazolylacetic acid derivative of the formula: ##STR1## wherein R.sup.1 is alkyl of one to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, phenyl or a substituted phenyl (said substituted phenyl being phenyl group substituted with one or two radicals selected from alkyl of one to 2 carbon atoms, alkoxy of one to 2 carbon atoms and halogen), and R.sup.2 is hydrogen or alkyl of one to 12 carbon atoms. The compound (I) is useful as a hypolipidemic agent.

  一种 furyloxazolylacetic 酸衍生物的化学式为：##STR1## 其中 R.sup.1 是1至6个碳原子的烷基，5至6个碳原子的环烷基，苯基或取代苯基（所述取代苯基是苯基，其上取代有一个或两个来自1至2个碳原子的烷基、1至2个碳原子的烷氧基和卤素的基团），而 R.sup.2 是氢或1至12个碳原子的烷基。该化合物（I）可用作降脂药剂。
• LARGE CONDUCTANCE CALCIUM-ACTIVATED K CHANNEL OPENER
  申请人：Hongu Mitsuya

  公开号：US20100256165A1

  公开（公告）日：2010-10-07

  A large conductance calcium-activated K channel opener comprising as an active ingredient a nitrogen-containing 5-membered heterocyclic compound represented by the following formula (I): wherein X represents N—R 4 , O or S, R 1 and R 2 each independently represent hydrogen, halogen, carboxyl, amino, lower alkyl, lower alkoxycarbonyl, lower alkenyl, cyclo-lower alkyl, carbamoyl, aryl, heterocyclic or heterocyclic-substituted carbonyl group, R 3 represents aryl, heterocyclic or lower alkyl group, and R 4 represents hydrogen or lower alkyl group, or a pharmaceutically acceptable salt thereof.

  一种大导电性钙激活的K通道开放剂，其作为活性成分是一种含氮的5元杂环化合物，表示为以下式子（I）：其中X代表N—R4，O或S，R1和R2各自独立地表示氢、卤素、羧基、氨基、低碳基、低碳氧基羰基、低烯基、环-低碳基、氨基甲酰基、芳基、杂环或杂环取代的羰基基团，R3表示芳基、杂环或低碳基团，R4表示氢或低碳基团，或其药学上可接受的盐。
• Furyloxazolylacetic acid derivative, processes for preparing same and pharmaceutical composition
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0120270A2

  公开（公告）日：1984-10-03

  A furyloxazolylacetic acid derivative of the formula: wherein R' is lower alkyl, R2 is hydrogen atom or lower alkyl, R3 is hydrogen atom or lower alkyl and ring A is phenyl or halogenophenyl, processes for preparing same and pharmaceutical compositions containing the new compounds, which are useful as a hypolipidemic agent are disclosed.

  一种式中R'为低级烷基，R2为氢原子或低级烷基，R3为氢原子或低级烷基，环A为苯基或卤素苯基的呋喃恶唑乙酸衍生物，其制备方法以及含有该衍生物的药物组合物： 其中R'为低级烷基，R2为氢原子或低级烷基，R3为氢原子或低级烷基，环A为苯基或卤代苯基，公开了制备这些新化合物的工艺和含有这些新化合物的药物组合物，它们可用作降血脂剂。
• J. Med. Chem. 1988, 31, 1197-1204
  作者：

  DOI：——

  日期：——
• MATSUMOTO, KADZUO;TAKASIMA, XIROSIGEH
  作者：MATSUMOTO, KADZUO、TAKASIMA, XIROSIGEH

  DOI：——

  日期：——