2-羟基苯甲亚氨酸乙酯 | 20857-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-羟基苯甲亚氨酸乙酯
• 英文名称: 2-hydroxybenzimino ethyl ether
• 英文别名: ethyl 2-hydroxybenzimidate；2-hydroxy-benzimidic acid ethyl ester；salicylimidic acid ethyl ester；Salicylsaeure-(aethylester-imin)；Salicylimidsaeure-aethylester；2-Hydroxybenzimidsaeure-aethylester；ethyl 2-hydroxybenzenecarboximidate
• CAS: 20857-12-9
• 化学式: C₉H₁₁NO₂
• mdl: MFCD09996125
• 分子量: 165.192
• InChiKey: VCGCYPPHDRMEFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  53.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  2-羟基苯甲亚氨酸乙酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 (4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid
  参考文献：
  名称：

  The Desferrithiocin Pharmacophore

  摘要：

  The (S)-desferrithiocin (DFT) skeleton is shown to be a useful pharmacophore on which to design orally effective iron chelators. While the study clearly indicates that formal reduction of the desazadesmethyldesferrithiocin thiazoline to a thiazolidine (6), expansion of the desmethyldesferrithiocin thiazoline to a thiazine (7), or substitution of the thiazoline sulfur of desazadesmethyldesferrithiocin by an oxygen (8 and 9) lead to a substantial loss of activity, conversion of (S)-desmethyldesferrithiocin (1) to an N-methylhydroxamate (4) or to the hexacoordinate dihydroxamate ligand (5) results in active compounds. This investigation thus demonstrates which structural components of the siderophore are required for iron clearance after oral administration and suggests the use of the desferrithiocin platform as a vector for other chelators.

  DOI：

  10.1021/jm00036a005
• 作为产物：
  描述：

  邻羟基苯甲腈 、 乙醇 在 盐酸 作用下， 生成 2-羟基苯甲亚氨酸乙酯
  参考文献：
  名称：

  Synthetic studies related to mycobactins. I. Synthesis of 2-(2'-Hydroxyphenyl)-2-oxazoline-4-carboxylic acid and related compounds

  摘要：

  介绍了几种制备 描述了 2-(2'-羟基苯基)-2-恶唑啉-4-羧酸的几种制备方法，以及对其化学反应性的研究。 的化学反应性的研究。 2-(2'-羟基苯基)-2-恶唑啉的化学反应性的研究。

  DOI：

  10.1071/ch9721797

文献信息

• 300-MHz proton study of parabactin and its gallium(III) chelate
  作者：Raymond J. Bergeron、Steven J. Kline

  DOI：10.1021/ja00323a004

  日期：1984.5

  Les spectres RMN de 1 H a 300 MHz montrent que le coordinat existe sous forme de 3 conformeres separes tandis que le chelate ne forme exclusivement que la forme Λ-cis. Discussion

  Les specters RMN de 1 H a 300 MHz montrent que le coordinatexiste sous forme de 3 conformeres separes tandis que le chelate ne forme exclusivement que la forme Λ-cis。讨论
• DESAZADESFERROTHIOCIN AND DESAZADESFERROTHIOCIN POLYETHER ANALOGUES AS METAL CHELATION AGENTS
  申请人：Malecha James

  公开号：US20110275636A1

  公开（公告）日：2011-11-10

  Disclosed herein are new compounds of desazadesferrothiocin polyether (DADFT-PE) analogues, as well as pharmaceutical compositions comprising them and their application as metal chelation agents for the treatment of disease. Methods of chelation of iron and other metals in a human or animal subject are also provided for the treatment of metal overload and toxicity.

  本文披露了新的去氮去除铁硫胺聚醚（DADFT-PE）类似物化合物，以及包含它们的药物组合物，以及它们作为金属螯合剂用于治疗疾病的应用。还提供了在人类或动物主体中螯合铁和其他金属的方法，用于治疗金属过载和中毒。
• Total Synthesis of Vulnibactin: A Natural Product Iron Chelator
  作者：Raymond Bergeron、Neelam Bharti、Shailendra Singh

  DOI：10.1055/s-2007-965960

  日期：2007.4

  A short, high-yield, flexible synthesis is described for accessing vulnibactin and related siderophores, e.g., vibriobactin analogues and homologues. The spectral properties of the synthetic vulnibactin are identical with those reported for the natural product, thus confirming the proposed structure of vulnibactin.

  本文描述了一种简短、高产、灵活的合成方法，可用于获得硫杆菌素和相关的苷元，如弧菌素类似物和同系物。合成的硫杆菌素的光谱特性与天然产物的光谱特性相同，从而证实了硫杆菌素的拟议结构。
• DESAZADESFERROTHIOCIN ANALOGUES AS METAL CHELATION AGENTS
  申请人：FerroKin BioSciences, Inc.

  公开号：US20150259306A1

  公开（公告）日：2015-09-17

  Disclosed herein are new compounds of desazadesferrothiocin polyether (DADFT-PE) analogues, as well as pharmaceutical compositions comprising them and their application as metal chelation agents for the treatment of disease. Methods of chelation of iron and other metals in a human or animal subject are also provided for the treatment of metal overload and toxicity.

  本文披露了新的去氮去铁硫单环醚（DADFT-PE）类似物化合物，以及包含它们的制药组合物，以及它们作为金属螯合剂用于治疗疾病的应用。还提供了用于治疗人类或动物主体中金属过载和毒性的铁和其他金属螯合方法。
• New synthetic probes of the iron transport system of Paracoccus denitrificans
  作者：George M. Buckley、Gerald Pattenden、Donald A. Whiting

  DOI：10.1016/s0040-4020(01)85669-6

  日期：1994.1

  A range of analogues of parabactin A 4 and agrobactin A 5 have been synthesised. All these comounds were able to chelate iron, and to promote the growth of iron-starved Paracoccus denitrificans to varying degrees. A degree of flexibilty in the siderophore receptor system is thus demonstrated which may be exploitable for the transport of new siderophore - antibiotic conjugates.