4-(2-benzoylhydrazinyl)-4-oxobutanoic acid | 20215-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-benzoylhydrazinyl)-4-oxobutanoic acid
• 英文别名: N-Benzoyl-N'-(3-carboxy-propionyl)-hydrazin；N²-Benzoylbernsteinsaeuremonohydrazid；N'-benzoyl-succinohydrazidic acid；succinic acid mono-(N'-benzoyl-hydrazide)；Bernsteinsaeure-mono-(N'-benzoyl-hydrazid)；Bernsteinsaeure-mono-benzhydrazid；Monobenzoyl-succinhydrazidsaeure；4-Oxo-4-[2-(phenylcarbonyl)hydrazinyl]butanoic acid
• CAS: 20215-79-6
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: BCAYFYHKUBCJIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-benzoylhydrazinyl)-4-oxobutanoic acid 在 硫酸 作用下， 生成 3-(5-苯基-1,3,4-噁二唑)丙酸
  参考文献：
  名称：

  Short,F.W.; Long,L.M., Journal of Heterocyclic Chemistry, 1969, vol. 6, p. 707 - 712

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 4-(2-benzoylhydrazinyl)-4-oxobutanoic acid
  参考文献：
  名称：

  Curtius, Journal fur praktische Chemie (Leipzig 1954), 1915, vol. <2>92, p. 102

  摘要：

  DOI：

文献信息

• Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion
  作者：Kar Kheng Yeoh、Mun Chiang Chan、Armin Thalhammer、Marina Demetriades、Rasheduzzaman Chowdhury、Ya-Min Tian、Ineke Stolze、Luke A. McNeill、Myung Kyu Lee、Esther C. Y. Woon、Mukram M. Mackeen、Akane Kawamura、Peter J. Ratcliffe、Jasmin Mecinović、Christopher J. Schofield

  DOI：10.1039/c2ob26648b

  日期：——

  Inhibition of the hypoxia-inducible factor (HIF) prolyl hydroxylases (PHD or EGLN enzymes) is of interest for the treatment of anemia and ischemia-related diseases. Most PHD inhibitors work by binding to the single ferrous ion and competing with 2-oxoglutarate (2OG) co-substrate for binding at the PHD active site. Non-specific iron chelators also inhibit the PHDs, both in vitro and in cells. We report the identification of dual action PHD inhibitors, which bind to the active site iron and also induce the binding of a second iron ion at the active site. Following analysis of small-molecule iron complexes and application of non-denaturing protein mass spectrometry to assess PHD2·iron·inhibitor stoichiometry, selected diacylhydrazines were identified as PHD2 inhibitors that induce the binding of a second iron ion. Some compounds were shown to inhibit the HIF hydroxylases in human hepatoma and renal carcinoma cell lines.

  翻译结果： 对缺氧诱导因子（HIF）脯氨酰羟化酶（PHD或EGLN酶）的抑制在治疗贫血和缺血相关疾病方面备受关注。大多数PHD抑制剂通过结合单个亚铁离子并与2-氧代戊二酸（2OG）共底物竞争结合PHD活性位点来发挥作用。非特异性铁螯合剂也能在体外和细胞内抑制PHD。我们报告了双作用PHD抑制剂的鉴定，这些抑制剂不仅与活性位点的铁结合，还能诱导在活性位点上结合第二个铁离子。通过对小分子铁络合物的分析并在非变性蛋白质谱法中评估PHD2·铁·抑制剂的比例后，鉴定出某些二酰基联氨为诱导第二个铁离子结合的PHD2抑制剂。有些化合物被证明能抑制人类肝癌和肾癌细胞系中的HIF羟化酶。
• Cavity-containing supramolecular gels as a crystallization tool for hydrophobic pharmaceuticals
  作者：Lena Kaufmann、Stuart R. Kennedy、Christopher D. Jones、Jonathan W. Steed

  DOI：10.1039/c6cc04037c

  日期：——

  We present two approaches to low-molecular-weight supramolecular gels bearing hydrophobic cavities based on calixarene-containing building blocks. Gels are formed by a calixarene based tetrahydrazide gelator or a co-gel of a...

  我们提出了两种方法，以低分子量超分子凝胶为基础，这些凝胶具有基于含杯芳烃的结构单元的疏水腔。凝胶是由基于杯芳烃的四酰肼胶凝剂或硅藻土的共凝胶形成的。
• 1,3,4-Oxadiazoles for Crystal Engineering. Convenient Synthesis and Self-Assembly: Nonchiral Chains versus Chiral Helices
  作者：Oleksii V. Gutov

  DOI：10.1021/cg400649h

  日期：2013.9.4

  A series of new 1,3,4-oxadiazoles containing carboxylic and halogen groups and a double bond have been synthesized in good yields and a multigram scale. This was achieved at room temperature from readily available 1,2-diacylhydrazines using a cheap condensation reagent (the solution of P2O5 in H2SO4). Single-crystal X-ray diffraction analysis has shown that all studied 1,3,4-oxadiazole-containing acids are self-assembled by intermolecular H-bonds into supramolecular zigzag chains or helices, depending on the tecton molecular structure and the type of H-bonding. Factors affecting helix formation have been found, and a Cambridge Structural Database (CSD) survey has been performed to support these findings. Moreover, it has been demonstrated that the tuning of the crystal structure leading to spontaneous symmetry breaking for supramolecular helices based on nonchiral molecules is possible even by as little change in molecular structure as a shift from an isopropyl substituent to a cyclopropyl. Subsequently, the studied 1,3,4-oxadiazole-containing acids and related compounds are found to be easily accessible building blocks for crystal engineering of new chiral materials with tunable supramolecular arrangement.
• Grekov,A.P.; Skripchenko,V.K., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, # 2, p. 236 - 238
  作者：Grekov,A.P.、Skripchenko,V.K.

  DOI：——

  日期：——
• [EN] NOVEL MDA-9 ANTAGONIST WITH ANTI-METASTATIC POTENTIAL<br/>[FR] NOUVEL ANTAGONISTE DE MDA -9 À POTENTIEL ANTI-MÉTASTATIQUE
  申请人：[en]VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：WO2022216930A1

  公开（公告）日：2022-10-13

  Disclosed herein are, inter cilia, compounds modulating activity and methods of use thereof for treating MDA-9/Syntenin associated conditions or disorders.