(Z)-4-对溴苯基-2-羟基-4-氧代-2-丁烯酸 | 103344-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (Z)-4-对溴苯基-2-羟基-4-氧代-2-丁烯酸
• 英文名称: (Z)-4-p-bromophenyl-2-hydroxy-4-oxo-2-butenoic acid
• 英文别名: (Z)-4-(4-bromophenyl)-2-hydroxy-4-oxobut-2-enoic acid
• CAS: 103344-72-5
• 化学式: C₁₀H₇BrO₄
• 分子量: 271.067
• InChiKey: MSIWJEWWOVPDSE-UITAMQMPSA-N

物化性质

• 熔点：
  158-163 °C
• 沸点：
  432.2±45.0 °C(Predicted)
• 密度：
  1.740±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-对溴苯基-2-羟基-4-氧代-2-丁烯酸 在 氯化亚砜 、 sodium acetate 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 29.0h， 生成 methyl 4-(4-bromophenyl)-2,4-dioxo-3-(phenylhydrazinylidene)butanoate
  参考文献：
  名称：

  Pimenova, E. V.; Andreichikov, Yu. S., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 2.2, p. 302 - 315

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(4-溴苯基)呋喃-2,3-二酮 在 水 作用下， 生成 (Z)-4-对溴苯基-2-羟基-4-氧代-2-丁烯酸
  参考文献：
  名称：

  Kozlov, A. P.; Sychev, D. I.; Andreichikov, Yu. S., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 10, p. 1965 - 1972

  摘要：

  DOI：

文献信息

• Diketo acids and their amino acid/dipeptidic analogues as promising scaffolds for the development of bacterial methionine aminopeptidase inhibitors
  作者：Mir Mohammad Masood、Vijay K. Pillalamarri、Mohammad Irfan、Babita Aneja、Mohamad Aman Jairajpuri、Md. Zafaryab、M. Moshahid A. Rizvi、Umesh Yadava、Anthony Addlagatta、Mohammad Abid

  DOI：10.1039/c5ra03354c

  日期：——

  Diketo acids and their peptidic analogues were designed and synthesised as bacterial MetAP inhibitors. In the enzymatic assay, the representative compound 5e showed excellent inhibition of bacterial MetAPs with no cytotoxicity.

  二酮酸及其肽类类似物被设计并合成为细菌MetAP抑制剂。在酶活性测定中，代表性化合物5e显示出对细菌MetAPs的优秀抑制作用，且无细胞毒性。
• 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。
• Chemistry of iminofurans 3. *Synthesis and intramolecular cyclization of (Z)-4-aryl- 2-[3-(ethoxycarbonyl)-4,5,6,7-tetra- hydrobenzo[b]thiophen-2-ylamino]- 4-oxobuten-2-oic acids
  作者：S. A. Shipilovskikh、A. E. Rubtsov、V. V. Zalesov

  DOI：10.1007/s10593-009-0334-3

  日期：2009.6

  (Z)-4-Aryl-2-[3-(ethoxycarbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino]-4-oxobuten-2-oic acids, which exist in the enamino keto form in solutions, were synthesized by the action of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate on 4-aryl-2-hydroxy-4-oxobuten-2-oic acids. Under the influence of acetic anhydride the obtained acids undergo cyclization to ethyl 2-(5-aryl-2-oxofuran-3(2H)-ylideneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates.
• ——
  作者：V. V. Zalesov、S. S. Kataev、N. A. Pulina、N. V. Kovylyaeva

  DOI：10.1023/a:1020343221719

  日期：——

  By treating 4-aryl-2,4-dioxobutanoic acids or their alkyl esters with diazomethane alkyl 4-aryl-2-methoxy-4-oxo-2-butenoates and 1-R-3-aroyl-4-methoxy-4-methoxycarbonyl-4,5-dihydropyrazoles were prepared. O-Alkyl derivatives and substituted pyrazoles were also obtained by reaction of 4-aryl-2,4-oxobutanoic acids aryl amides with diazomethane and diazoethane.
• Nekrasov, D. D.; Shurov, S. N.; Ivanenko, O. I., Russian Journal of Organic Chemistry, 1994, vol. 30, # 1, p. 136 - 142
  作者：Nekrasov, D. D.、Shurov, S. N.、Ivanenko, O. I.、Andreichikov, Yu. S.

  DOI：——

  日期：——