ethyl 2,3-dihydroxybenzimidate | 96649-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 2,3-dihydroxybenzimidate
• 英文别名: ethyl 2,3-dihydroxybenzenecarboximidate
• CAS: 96649-28-4
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: LLPPJWIMLXBXLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  73.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-dihydroxybenzimidate 、 N⁴-(L-threonyl)-N¹,N⁷-bis(2,3-dihydroxybenzoyl)norspermidine hydrochloride 以 甲醇 为溶剂， 反应 30.0h， 以65%的产率得到fluvibactin
  参考文献：
  名称：

  不对称位点在选择铁载体作为延缓剂中的意义。

  摘要：

  描述了微生物铁螯合剂L-氟维巴汀，其非天然对映体，D-氟维巴汀，L-高氟维巴汀和L-agrobactin的合成。关键步骤包括在1,1-羰基二咪唑存在下，用2,3-双（苄氧基）苯甲酸将鸟精胺，亚精胺或高精胺的末端氮选择性双酰化，然后偶联N-羟基琥珀酰亚胺酯CBZ保护的L-或D-苏氨酸与中心氮的连接 评估了每种配体在低铁环境中支持反硝化副球菌生长的有效性以及这些化合物促进铁吸收的能力。恶唑啉环的立体化学构型显示是控制微生物生长刺激和铁吸收的主要结构因素。L-黄杆菌素 L-高氟尿素和L-agrobactin均能促进生长和铁的吸收。D-氟维巴汀仅略微活跃。与微生物的天然铁载体L-parabactin一样，所研究的L-构型的所有三个配体均表现出双相动力学，即高亲和力和低亲和力。高亲和力系统（铁浓度<1 microM）产生的K（m）值介于0.11至0.23 microM之间，而V（max）值介于157至129

  DOI：

  10.1021/jm010019s
• 作为产物：
  描述：

  ethyl 2,3-bis(benzyloxy)benzimidate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.92h， 以73%的产率得到ethyl 2,3-dihydroxybenzimidate
  参考文献：
  名称：

  An efficient total synthesis of agrobactin and its gallium(III) chelate

  摘要：

  DOI：

  10.1021/jo00215a037

文献信息

• 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。
• Siderophore Conjugate Immunogenic Compositions and Vaccines
  申请人：Bergeron, JR. Raymond J.

  公开号：US20120052087A1

  公开（公告）日：2012-03-01

  An immunogenic composition comprising a siderophore covalently linked to a pharmaceutically acceptable carrier molecule wherein the antigenicity of the siderophore moiety is sufficient to stimulate an immuno-logic response to the siderophore when the composition is circulating in the bloodstream of a human or non-human animal and vaccine.

  一种免疫原性组合物，包括一个与药用可接受载体分子共价连接的铁载体，其中铁载体部分的抗原性足以在该组合物在人类或非人类动物的血液循环中循环时刺激对铁载体的免疫反应，从而形成疫苗。
• SIDEROPHORE CONJUGATE IMMUNOGENIC COMPOSITIONS AND VACCINES
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20150071961A1

  公开（公告）日：2015-03-12

  An immunogenic composition comprising a siderophore covalently linked to a pharmaceutically acceptable carrier molecule wherein the antigenicity of the siderophore moiety is sufficient to stimulate an immunologic response to the siderophore when the composition is circulating in the bloodstream of a human or non-human animal and vaccine.

  一种免疫原性组合物，包括一个与药学上可接受的载体分子共价结合的铁载体，其中铁载体基团的抗原性足以在人类或非人类动物的血液循环中刺激对铁载体的免疫反应，从而形成疫苗。
• Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators
  作者：Raymond J. Bergeron、Jan Wiegand、William R. Weimar、J. R. Timothy Vinson、Jörg Bussenius、Guo Wei Yao、James S. McManis

  DOI：10.1021/jm980340j

  日期：1999.1.1

  Further structure-activity studies of desferrithiocin analogues are carried out. (S)-desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous imp act on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Delta(2)-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.
• Vibriobactin Antibodies: A Vaccine Strategy
  作者：Raymond J. Bergeron、Neelam Bharti、Shailendra Singh、James S. McManis、Jan Wiegand、Linda G. Green

  DOI：10.1021/jm900119q

  日期：2009.6.25

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.