cis-2,3-epoxysuccinamic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: cis-2,3-epoxysuccinamic acid
• 英文别名: (±)-cis-2,3-epoxysuccinamic acid；(2R,3S)-3-carbamoyloxirane-2-carboxylic acid
• 化学式: C₄H₅NO₄
• 分子量: 131.088
• InChiKey: FCFUXIZBMYCYHI-NHYDCYSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-2,3-epoxysuccinamic acid 、 4-硝基-4'-氨基二苯醚 在 二甲基氨基丙基乙基碳酰胺 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以38%的产率得到(2SR,3RS)-N²-(4-(4-nitrophenoxy)phenyl)oxirane-2,3-dicarboxamide
  参考文献：
  名称：

  (±) cis-bisamido epoxides: A novel series of potent FXIII-A inhibitors

  摘要：

  A novel class of potent FXIII-A inhibitors containing a (+/-) cis-bisamido epoxide pharmacophore is described. The compounds display highly potent inhibition of FXIII-A (IC50 = 5-500 nM) in an in vitro assay. In contrast to other types of previously described covalent transglutaminase inhibitors, the bis-amido epoxides exhibited no measurable reactivity with glutathione, therefore possibly rendering this class of compounds suitable for future in vivo investigations. Additionally, the compounds show selective inhibition for FXIII-A against the cysteine protease, cathepsin S although they proved to have similar potency with a closely related transglutaminase, TGII, to that observed for FXIII-A. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.019
• 作为产物：
  描述：

  cis-2,3-epoxysuccinic anhydride 在 六甲基二硅氮烷 作用下， 以 乙醚 为溶剂， 反应 96.0h， 以63%的产率得到cis-2,3-epoxysuccinamic acid
  参考文献：
  名称：

  铜蓝蛋白二羧酸类似物的制备

  摘要：

  我们已经提出并合成了一些新的结构型天蓝素类似物，它们具有作为脂肪酸和聚酮化合物合酶多酶复合物抑制剂的潜力。这些类似物含有带有侧翼羧酸盐基团的顺式环氧化物。我们的合成物经过精心设计，可以在四到五个步骤中以收敛的方式从易得的起始原料中获得各种脂肪酸和类似聚酮化合物的侧链。总共已经制备并表征了约40种潜在的类似物，涵盖了所提出的所有结构亚类，其中大多数构成了新颖的功能组。

  DOI：

  10.1002/jhet.5570420511

文献信息

• Preparation of dicarboxylate analogues of cerulenin
  作者：Jonathan D. Moseley、James Staunton

  DOI：10.1002/jhet.5570420511

  日期：2005.7

  We have proposed and synthesized several new structural classes of Cerulenin analogues, which have potential as inhibitors of both fatty acid and polyketide synthase multi-enzyme complexes. These analogues contain cis epoxides bearing flanking carboxylate groups. Our syntheses have been designed to allow access to a wide range of fatty acid and polyketide-like side chains from readily available starting

  我们已经提出并合成了一些新的结构型天蓝素类似物，它们具有作为脂肪酸和聚酮化合物合酶多酶复合物抑制剂的潜力。这些类似物含有带有侧翼羧酸盐基团的顺式环氧化物。我们的合成物经过精心设计，可以在四到五个步骤中以收敛的方式从易得的起始原料中获得各种脂肪酸和类似聚酮化合物的侧链。总共已经制备并表征了约40种潜在的类似物，涵盖了所提出的所有结构亚类，其中大多数构成了新颖的功能组。
• (±) cis-bisamido epoxides: A novel series of potent FXIII-A inhibitors
  作者：Craig A. Avery、Richard J. Pease、Kerrie Smith、May Boothby、Helen M. Buckley、Peter J. Grant、Colin W.G. Fishwick

  DOI：10.1016/j.ejmech.2015.05.019

  日期：2015.6

  A novel class of potent FXIII-A inhibitors containing a (+/-) cis-bisamido epoxide pharmacophore is described. The compounds display highly potent inhibition of FXIII-A (IC50 = 5-500 nM) in an in vitro assay. In contrast to other types of previously described covalent transglutaminase inhibitors, the bis-amido epoxides exhibited no measurable reactivity with glutathione, therefore possibly rendering this class of compounds suitable for future in vivo investigations. Additionally, the compounds show selective inhibition for FXIII-A against the cysteine protease, cathepsin S although they proved to have similar potency with a closely related transglutaminase, TGII, to that observed for FXIII-A. (C) 2015 Elsevier Masson SAS. All rights reserved.