(Z)-4-(benzofuran-2-yl)-2-hydroxy-4-oxobut-2-enoic acid | 1224740-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (Z)-4-(benzofuran-2-yl)-2-hydroxy-4-oxobut-2-enoic acid
• 英文别名: (Z)-4-(benzofuran-2-yl)-2-hydroxy-4-oxo-but-2-enoic acid；(Z)-4-(1-benzofuran-2-yl)-2-hydroxy-4-oxobut-2-enoic acid
• CAS: 1224740-10-6
• 化学式: C₁₂H₈O₅
• 分子量: 232.193
• InChiKey: KPSMALWRUGTEPI-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-5-(2-(benzofuran-2-yl)-2-oxoethylidene)-2,2-dimethyl-1,3-dioxolan-4-one 在 sodium hydroxide 作用下， 以 水 为溶剂， 以95%的产率得到(Z)-4-(benzofuran-2-yl)-2-hydroxy-4-oxobut-2-enoic acid
  参考文献：
  名称：

  (Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives

  摘要：

  The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected alpha,gamma-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric acid along with its acid chloride was used to prepare ester, amide, and aryl derivatives. The dioxolane moiety was found to be a convenient functionality that facilitated ready unmasking by straightforward hydrolysis to reveal alpha,gamma-diketoacid derivatives or derivatization to yield ester, amide, and 2,3-pyrrolidinedione derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.032

文献信息

• Inhibitors of Mycobacterium Tuberculosis Malate Synthase, Methods of Making and Uses Thereof
  申请人：Freundlich Joel S.

  公开号：US20140171444A1

  公开（公告）日：2014-06-19

  The present invention provides aryl- or heteroaryl-diketo acid compounds effective to inhibit an activity of a Mycobacterial malate synthase enzyme or to inhibit a malate synthase activity in other bacteria having the enzyme. The compounds may be phenyl- naphthyl-, or thienyl-substituted diketo acids and carboxylate derivatives thereof. Also provided are methods of treating tuberculosis or other pathophysiological conditions associated with a malate synthase enzyme with the inhibitory compounds and methods of in silico design of the inhibitory compounds. In addition, the present invention provides the inhibitory compounds designed by this method. Furthermore, three-dimensional X-ray crystal structures of the Mycobacterial malate synthase complexed with the inhibitory compounds are provided. Further still a method for stabilizing an aromatic or heteroaromatic diketo acid or its prodrug or close analog in solution by derivatizing at least the ortho position on the aromatic ring is provided.

  本发明提供了芳基或杂环芳基二酮酸化合物，其能够有效抑制结核分枝杆菌苹果酸合酶酶活性或抑制其他具有该酶的细菌的苹果酸合酶活性。这些化合物可以是苯基、萘基或噻吩基取代的二酮酸和其羧酸衍生物。还提供了使用这些抑制剂治疗结核病或其他与苹果酸合酶酶相关的病理生理状况的方法以及通过计算机模拟设计这些抑制剂的方法。此外，本发明还提供了通过这种方法设计的抑制剂。此外，还提供了与抑制剂形成复合物的结核分枝杆菌苹果酸合酶的三维X射线晶体结构。还提供了一种通过在芳香环上至少衍生化邻位位置来稳定溶液中的芳香或杂环芳香二酮酸或其前药或类似物的方法。
• Inhibitors of mycobacterium tuberculosis malate synthase, methods of making and uses thereof
  申请人：Freundlich Joel S.

  公开号：US20100113477A1

  公开（公告）日：2010-05-06

  The present invention provides aryl- or heteroaryl-diketo acid compounds effective to inhibit an activity of a Mycobacterial malate synthase enzyme or to inhibit a malate synthase activity in other bacteria having the enzyme. The compounds may be phenyl-naphthyl-, or thienyl-substituted diketo acids and carboxylate derivatives thereof. Also provided are methods of treating tuberculosis or other pathophysiological conditions associated with a malate synthase enzyme with the inhibitory compounds and methods of in silico design of the inhibitory compounds. In addition, the present invention provides the inhibitory compounds designed by this method. Furthermore, three-dimensional X-ray crystal structures of the Mycobacterial malate synthase complexed with the inhibitory compounds are provided. Further still a method for stabilizing an aromatic or heteroaromatic diketo acid or its prodrug or close analog in solution by derivatizing at least the ortho position on the aromatic ring is provided.
• US8664255B2
  申请人：——

  公开号：US8664255B2

  公开（公告）日：2014-03-04
• (Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives
  作者：Jacques Banville、Gilles Bouthillier、Serge Plamondon、Roger Remillard、Nicholas A. Meanwell、Alain Martel、Michael A. Walker

  DOI：10.1016/j.tetlet.2010.04.032

  日期：2010.6

  The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected alpha,gamma-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric acid along with its acid chloride was used to prepare ester, amide, and aryl derivatives. The dioxolane moiety was found to be a convenient functionality that facilitated ready unmasking by straightforward hydrolysis to reveal alpha,gamma-diketoacid derivatives or derivatization to yield ester, amide, and 2,3-pyrrolidinedione derivatives. (C) 2010 Elsevier Ltd. All rights reserved.