dimethyl (2S,3R)-2-hydroxy-3-butylsuccinate | 345347-50-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (2S,3R)-2-hydroxy-3-butylsuccinate
• 英文别名: (2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester；dimethyl (2R,3S)-2-butyl-3-hydroxybutanedioate
• CAS: 345347-50-4
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: GLQFRMFDOZOFOU-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (2S,3R)-2-hydroxy-3-butylsuccinate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid
  参考文献：
  名称：

  Novel succinate compounds, compositions and methods of use and preparation

  摘要：

  揭示了一种新型羟羧酸化合物。这些羟羧酸酯抑制肽变形酶（PDF），这是一种存在于原核生物中的酶。这些羟羧酸酯可用作抗微生物和抗生素。该发明的化合物表现出对肽变形酶的选择性抑制，而不影响其他金属蛋白酶如基质金属蛋白酶（MMPs）。该文还揭示了这些化合物的合成方法和使用方法。

  公开号：

  US20020115863A1
• 作为产物：
  描述：

  L-苹果酸二甲酯 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成 dimethyl (2S,3R)-2-hydroxy-3-butylsuccinate
  参考文献：
  名称：

  α-Substituted hydroxamic acids as novel bacterial deformylase inhibitor-based antibacterial agents

  摘要：

  We report the synthesis and biological activity of analogues of VRC3375 (N-hydroxy-3-R-butyl-3-[(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl]propionamide), an orally active peptide deformylase inhibitor. This study explores the structureactivity relationship of various chelator groups, alpha substituents, P-2' and P-3' substituents in order to achieve optimal antibacterial activity with minimal toxicity liability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.020

文献信息

• Novel succinate compounds, compositions and methods of use and preparation
  申请人：——

  公开号：US20020115863A1

  公开（公告）日：2002-08-22

  Novel hydroxamic acid compounds are disclosed. These hydroxamates inhibit peptidyl deformylase (PDF), an enzyme present in prokaryotes. The hydroxymates are useful as antimicrobials and antibiotics. The compounds of the invention display selective inhibition of peptidyl deformylase versus other metalloproteinases such as matrix metalloproteinases (MMPs). Methods of synthesis and of use of the compounds are also disclosed.

  揭示了一种新型羟羧酸化合物。这些羟羧酸酯抑制肽变形酶（PDF），这是一种存在于原核生物中的酶。这些羟羧酸酯可用作抗微生物和抗生素。该发明的化合物表现出对肽变形酶的选择性抑制，而不影响其他金属蛋白酶如基质金属蛋白酶（MMPs）。该文还揭示了这些化合物的合成方法和使用方法。
• Antifungal Activity of Homoaconitate and Homoisocitrate Analogs
  作者：Maria Milewska、Marta Prokop、Iwona Gabriel、Marek Wojciechowski、Sławomir Milewski

  DOI：10.3390/molecules171214022

  日期：——

  Thirteen structural analogs of two initial intermediates of the L-a-aminoadipate pathway of L-lysine biosynthesis in fungi have been designed and synthesized, including fluoro- and epoxy-derivatives of homoaconitate and homoisocitrate. Some of the obtained compounds exhibited at milimolar range moderate enzyme inhibitory properties against homoaconitase and/or homoisocitrate dehydrogenase of Candida albicans. The structural basis for homoisocitrate dehydrogenase inhibition was revealed by molecular modeling of the enzyme-inhibitor complex. On the other hand, the trimethyl ester forms of some of the novel compounds exhibited antifungal effects. The highest antifungal activity was found for trimethyl trans-homoaconitate, which inhibited growth of some human pathogenic yeasts with minimal inhibitory concentration (MIC) values of 16–32 mg/mL.

  我们设计并合成了真菌 L-赖氨酸生物合成途径中 L-a-氨基己二酸盐两个初始中间体的 13 种结构类似物，包括高乌头酸盐和高异柠檬酸盐的氟和环氧衍生物。其中一些化合物在毫摩尔范围内对白色念珠菌的高乌头酸酶和/或高异柠檬酸脱氢酶表现出适度的酶抑制特性。酶-抑制剂复合物的分子模型揭示了同异柠檬酸脱氢酶抑制作用的结构基础。另一方面，一些新型化合物的三甲酯形式显示出抗真菌作用。反式高乌头酸三甲酯的抗真菌活性最高，它能抑制一些人类致病酵母菌的生长，最小抑制浓度（MIC）值为 16-32 毫克/毫升。
• Novel pyrrolidine bicyclic compounds and its derivatives, compositions and methods of use
  申请人：Jacobs Jeffrey

  公开号：US20050277683A1

  公开（公告）日：2005-12-15

  N-[1-oxo-(optionally 2-aza)-2-alkyl-3-(carboxyl or thiol or hydroxyaminocarbonyl or N-hydroxyformamido)-propyl]-(aryl or heteroaryl)-azacyclo 4-7 alkanes or thiazacyclo 4-7 alkanes, salts or prodrugs thereof have interesting properties, e.g., in the treatment or prevention of disorders amenable to treatment by PDF inhibitors, such as treatment of bacterial infections.

  N-[1-氧代（可选2-氮杂）-2-烷基-3-（羧基或硫醇或羟胺甲酰或N-羟基甲酰胺基）-丙基]-(芳基或杂芳基)-氮杂环4-7烷或硫杂环4-7烷，其盐或前药具有有趣的特性，例如，在PDF抑制剂治疗可治疗的疾病，如治疗细菌感染方面具有治疗或预防的作用。
• Succinate compounds, compositions and methods of use and preparation
  申请人：Vicuron Pharmaceuticals Inc.

  公开号：US06797820B2

  公开（公告）日：2004-09-28

  Novel hydroxamic acid compounds are disclosed. These hydroxamates inhibit peptidyl deformylase (PDF), an enzyme present in prokaryotes. The hydroxymates are useful as antimicrobials and antibiotics. The compounds of the invention display selective inhibition of peptidyl deformylase versus other metalloproteinases such as matrix metalloproteinases (MMPs). Methods of synthesis and of use of the compounds are also disclosed.

  本发明揭示了新型羟肟酸化合物。这些羟肟酸盐抑制蛋白酶酰基去形成酶（PDF），该酶存在于原核生物中。这些羟肟酸盐可用作抗微生物和抗生素。本发明的化合物在选择性抑制蛋白酶酰基去形成酶方面优于其他金属蛋白酶如基质金属蛋白酶（MMPs）。本发明还揭示了该化合物的合成和使用方法。
• Pyrrolidine bicyclic compounds and its derivatives, compositions and methods of use
  申请人：Vicuron Pharmaceuticals, Inc.

  公开号：US07612059B2

  公开（公告）日：2009-11-03

  N-[1-oxo-(optionally 2-aza)-2-alkyl-3-(carboxyl or thiol or hydroxyaminocarbonyl or N-hydroxyformamido)-propyl]-(aryl or heteroaryl)-azacyclo4-7alkanes or thiazacyclo4-7alkanes, salts or prodrugs thereof have interesting properties, e.g., in the treatment or prevention of disorders amenable to treatment by PDF inhibitors, such as treatment of bacterial infections.

  N-[1-氧代（可选2-氮杂）-2-烷基-3-（羧基或硫醇或羟胺甲酰基或N-羟基甲酰胺基）-丙基]-(芳基或杂芳基)-氮杂环4-7烷或硫杂环4-7烷，其盐或前药具有有趣的性质，例如，在PDF抑制剂治疗可治疗的紊乱，如细菌感染的治疗或预防方面具有作用。