α-carbomethoxytetramic acid | 37772-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: α-carbomethoxytetramic acid
• 英文别名: Methyl 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate；methyl 3-hydroxy-5-oxo-1,2-dihydropyrrole-4-carboxylate
• CAS: 37772-85-3
• 化学式: C₆H₇NO₄
• 分子量: 157.126
• InChiKey: DANTWGGJJYWTIA-UHFFFAOYSA-N

物化性质

• 熔点：
  >270 °C
• 沸点：
  389.4±42.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-carbomethoxytetramic acid 以 乙腈 为溶剂， 以95%的产率得到2,4-吡咯烷二酮
  参考文献：
  名称：

  Tetramic Acids as Scaffolds: Synthesis, Tautomeric and Antibacterial Behaviour

  摘要：

  报道了四咪酸在环氮上有各种取代基的高效合成途径、它们在溶液中的互变行为及其抗菌活性。

  DOI：

  10.1055/s-0029-1217745
• 作为产物：
  描述：

  N-Acetyl-α-carbomethoxytetramic acid 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以51%的产率得到α-carbomethoxytetramic acid
  参考文献：
  名称：

  Igglessi-Markopoulou, Olga; Sandris, Constantine, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1599 - 1606

  摘要：

  DOI：

文献信息

• One-pot synthesis of azabicyclic peroxides from tetramic acid derivatives by manganese(III)-mediated oxidative [2+2+2]cycloaddition
  作者：Firoz Alam Chowdhury、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1016/s0040-4039(98)01765-1

  日期：1998.10

  A simple azabicyclic peroxide synthesis was achieved by the manganese(III)-mediated oxidative formal [2+2+2] cycloaddition. A mixture of tetramic acid derivatives and alkenes was oxidized with manganese(III) acetate under a dry air stream to give 1-hydroxy-8-aza-2,3-dioxabicyclo[4.3.0]nonan-7-ones in good to quantitative chemical yields.

  一个简单的氮杂双环过氧化物合成是通过锰（III）介导的氧化式[2 + 2 + 2]环加成反应实现的。在干燥空气流下，用乙酸锰（III）氧化四酸衍生物和烯烃的混合物，得到定量至良好的1-羟基-8-氮杂-2,3-二氧杂双环[4.3.0]壬南-7-酮。化学收率。
• Design, synthesis and microbiological evaluation of ampicillin–tetramic acid hybrid antibiotics
  作者：Philip T Cherian、Aditi Deshpande、Martin N Cheramie、David F Bruhn、Julian G Hurdle、Richard E Lee

  DOI：10.1038/ja.2016.52

  日期：2017.1

  activities of the hybrids improved in the presence of clavulanic acid revealing that the tetramic acid moiety did not provide added protection against β-lactamases. In addition, the hybrids were found to be efflux pump substrates as their activities markedly improved against pump-inactivated strains. Unlike the catechol and hydroxamic acid siderophore β-lactam conjugates, the activities of the hybrids did not

  通过将β-内酰胺抗生素与铁螯合剂（例如儿茶酚和异羟肟酸）结合来利用铁吸收途径是克服革兰氏阴性细菌中与通透性相关的抗性的行之有效的策略。由于先前尚未为此目的检查过天然存在的铁螯合的四酸，因此设计并合成了一系列探索性新结构的氨苄青霉素-四酸杂种，这些杂物在结构上与尿嘧啶青霉素相似。针对具有代表性的临床上重要的细菌病原体，评估了新的类似物的螯合铁的能力及其MIC活性。tetra酸β-内酰胺杂化物表现出对铁的高亲和力，约为10 -30 M 3。杂种对革兰氏阳性细菌的活性较低。然而，针对革兰氏阴性细菌，它们的活性是依赖于物种的，与几种杂种相比，杂种表现出比氨苄西林更高的针对野生型铜绿假单胞菌的活性。在棒酸存在下，杂种的抗-Gram负活性得到了改善，这表明tetra酸部分并未提供针对β-内酰胺酶的额外保护作用。此外，发现杂种是外排泵底物，因为它们的活性明显增强，可抵抗泵灭活的菌株。与邻苯二酚和异羟肟酸
• Studies on the Synthesis and Bioactivities of 4-Amino Derivatives of Tetramic Acid
  作者：Yu-Xiu Liu、Hua-Ping Zhao、Hai-Bin Song、Yu-Cheng Gu、Qing-Min Wang

  DOI：10.1002/jhet.2004

  日期：2014.8

  In order to study the potential bioactivities of 4-amino tetramic acid derivatives, the 4-amination products of pyrrolidine-2,4-diones () and 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates () were prepared. The 4-amination of took place in high yield when catalyzed by acetic acid, whereas the 4-amination of was achieved through a 4-ethoxy intermediate, which was prepared by acidic etherification

  为了研究4-氨基四酸衍生物的潜在生物活性，吡咯烷-2,4-二酮的4-氨基化产物（）和4-羟基-2-氧代-2,5-二氢-1 H-吡咯-3-羧酸盐（）已准备好。4胺化当用乙酸催化时发生高收率，而乙酸的4-胺化通过4-乙氧基中间体制备，该中间体是通过酸性醚化制备的。测试了它们的除草，杀真菌，杀虫和抗肿瘤活性。生物测定表明，两种化合物在浓度为10 µg / mL时对双子叶拟南芥具有良好的除草活性，一种化合物对腐霉菌具有本能的杀真菌活性。浓度为2 µg / mL。
• Design and structure–activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones
  作者：Stefan Peukert、Yingchuan Sun、Rui Zhang、Brian Hurley、Mike Sabio、Xiaoyu Shen、Christen Gray、JoAnn Dzink-Fox、Jianshi Tao、Regina Cebula、Sompong Wattanasin

  DOI：10.1016/j.bmcl.2008.02.009

  日期：2008.3

  Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one- 3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure - activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided. (C) 2008 Elsevier Ltd. All rights reserved.
• Igglessi-Markopoulou, Olga; Sandris, Constantine, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 883 - 890
  作者：Igglessi-Markopoulou, Olga、Sandris, Constantine

  DOI：——

  日期：——