ethyl (2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetate | 145663-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl (2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetate
• 英文别名: ethyl 2-[2-(prop-2-enoxycarbonylamino)-1,3-thiazol-4-yl]acetate
• CAS: 145663-66-7
• 化学式: C₁₁H₁₄N₂O₄S
• mdl: MFCD02325259
• 分子量: 270.309
• InChiKey: CKWVKCFWAWPFOW-UHFFFAOYSA-N

物化性质

• 密度：
  1.293±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetate 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 (4S,5R,6S)-3-[(4-Ethoxycarbonylmethyl-thiazol-2-ylamino)-methyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Mitsunobu反应在合成C-2 N-甲基碳青霉烯中的新应用

  摘要：

  N-酰基酰胺和N-酰基氨基杂环可以在Mitsunobu条件下与C-2羟甲基碳青霉烯发生区域选择性反应：酰胺的合成，氨基杂环的环外烷基化和转化为2-氨基甲基碳青霉烯的报道。

  DOI：

  10.1016/s0040-4039(00)60855-9
• 作为产物：
  描述：

  2-氨基-4-噻唑乙酸乙酯 、 氯甲酸烯丙酯 在 吡啶 作用下， 反应 15.5h， 以67.8%的产率得到ethyl (2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetate
  参考文献：
  名称：

  Discovery of hydroxamic acid analogs as dual inhibitors of phosphodiesterase-1 and -5

  摘要：

  HTS and the following synthesis of a series of the compounds led us to the discovery of hydroxamic acid analogs as potent dual inhibitors of phosphodiesterase (PDE)-1 and 5. These compounds have highly related structure and deviation of the structure usually resulted in reduced potency. This result can be used to design other molecules that may be utilized for the therapy of cardiovascular symptoms that relates to cGMP level. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.016

文献信息

• THIAZOLE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP1921074A1

  公开（公告）日：2008-05-14

  [Problem] To provide a compound which is useful as a GK activator. [Means for Resolution] As a result of an extensive study on thiazole derivatives, the present inventors have found that a compound having an oxamoyl group, a glycol group or the like on a thiazole ring and a compound having an acetamide group substituted by a bicyclic heteroaryl group such as a quinolyl have a good GK activation effect, and thereby have accomplished the present invention. Since the compounds of the present invention have a good GK activation effect, these are useful as therapeutic agents for diabetes, particularly type II diabetes.

  [问题] 提供一种作为GK激活剂有用的化合物。[解决方法] 通过对噻唑衍生物进行广泛研究，本发明人发现，在噻唑环上具有氧羰基、甘醇基或类似基团的化合物，以及在乙酰胺基团上被双环杂环芳基团（如喹啉基）取代的化合物具有良好的GK激活效果，从而完成了本发明。由于本发明的化合物具有良好的GK激活效果，因此它们可用作糖尿病的治疗药物，特别是II型糖尿病。
• Discovery of hydroxamic acid analogs as dual inhibitors of phosphodiesterase-1 and -5
  作者：Akihito Dan、Takaaki Shiyama、Kazuto Yamazaki、Naoto Kusunose、Katsuya Fujita、Hideshi Sato、Kazutaka Matsui、Masafumi Kitano

  DOI：10.1016/j.bmcl.2005.06.016

  日期：2005.9

  HTS and the following synthesis of a series of the compounds led us to the discovery of hydroxamic acid analogs as potent dual inhibitors of phosphodiesterase (PDE)-1 and 5. These compounds have highly related structure and deviation of the structure usually resulted in reduced potency. This result can be used to design other molecules that may be utilized for the therapy of cardiovascular symptoms that relates to cGMP level. (c) 2005 Elsevier Ltd. All rights reserved.
• New applications of the mitsunobu reaction in the synthesis of C-2 N-methyl carbapenems
  作者：J.C. Arnould、F. Landier、M.J. Pasquet

  DOI：10.1016/s0040-4039(00)60855-9

  日期：1992.11

  N-acyl amides and N-acylamino heterocycles can be reacted regioselectively with C-2 hydroxymethyl carbapenems under Mitsunobu conditions:synthesis of amides, exocyclic alkylation of amino heterocycles and transformation into 2-aminomethyl carbapenems are reported.

  N-酰基酰胺和N-酰基氨基杂环可以在Mitsunobu条件下与C-2羟甲基碳青霉烯发生区域选择性反应：酰胺的合成，氨基杂环的环外烷基化和转化为2-氨基甲基碳青霉烯的报道。