(+)-(1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid | 186541-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid
• 英文别名: (+)(6S)-2oxobicyclo[3.1.0]hexane-6-carboxylic acid；(1S,5R,6S)-2-Oxobicyclo[3.1.0]hexane-6-carboxylic acid
• CAS: 186541-47-9
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: JUIOQBDYJXJVSZ-PUFIMZNGSA-N

物化性质

• 沸点：
  328.6±25.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid 在 乙醇 、 硫酸 作用下， 反应 1.25h， 以80%的产率得到(1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] PRODRUGS OF EXCITATORY AMINO ACIDS
  [FR] PROMEDICAMENTS D'ACIDES AMINES EXCITATEURS

  摘要：

  公开号：

  WO2003104217A3
• 作为产物：
  描述：

  (+) (6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid N-benzyl-α-methylbenzylamine salt 在 sodium hydroxide 、 盐酸 、 sodium chloride 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 以99%的产率得到(+)-(1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid
  参考文献：
  名称：

  [EN] PRODRUGS OF EXCITATORY AMINO ACIDS
  [FR] PROMEDICAMENTS D'ACIDES AMINES EXCITATEURS

  摘要：

  公开号：

  WO2003104217A3

文献信息

• [EN] TRIAZOLE CARBOXYLIC ACIDS AS LPA ANTAGONISTS<br/>[FR] ACIDES TRIAZOLE CARBOXYLIQUES EN TANT QU'ANTAGONISTES DE LPA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2020257135A1

  公开（公告）日：2020-12-24

  The present invention provides compounds of Formula (I), or a stereoisomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.

  本发明提供了式（I）的化合物，或其立体异构体、互变异构体、或药学上可接受的盐或溶剂，其中所有变量如本文所定义。这些化合物是选择性LPA受体抑制剂。
• Method of resolving 2-oxobicyclo &lsqb;3.1.0&rsqb; hexane-6-carboxylic acid derivatives
  申请人：Sumitomo Chemical Company, Limited

  公开号：US06407284B1

  公开（公告）日：2002-06-18

  There is disclosed a method of resolving 2-oxobicyclo[3.1.0]hexane-6-carboxylates having the following relative configuration of formula (1): wherein X1, X2, R1, R2 and R3 have the same meanings as defined below, into one enantiomer ester thereof and the other enantiomer acid, which is characterized by contacting an enzyme having an ability to preferentially hydrolyze one enantiomer ester contained in 2-oxobicyclo[3.1.0]hexane-6-carboxylate of formula (1) as defined above, with 2-oxobicyclo[3.1.0]hexane-6-carboxylates of formula (1) as defined above to obtain one enantiomer as an acid and the other enantiomer as an ester.

  公开了一种将具有以下相对构型的2-氧代双环[3.1.0]己烷-6-羧酸酯（式（1））解决为其中一个对映异构体酯和另一个对映异构体酸的方法，其中X1、X2、R1、R2和R3的含义如下所定义，其特征在于将具有优先水解式（1）中定义的2-氧代双环[3.1.0]己烷-6-羧酸酯中的一个对映异构体酯的能力的酶与上述定义的式（1）中定义的2-氧代双环[3.1.0]己烷-6-羧酸酯接触，以获得一个对映异构体作为酸，另一个对映异构体作为酯。
• The synthesis of isotopically labeled (+)-2-aminobicyclo[3.1.0]hexane-2,6-carboxylic acid and its 2-oxa- and 2-thia-analogs
  作者：William J. Wheeler、Douglas D. O'Bannon、Joseph H. Kennedy、James A. Monn、Roger W. Tharp-Taylor、Matthew J. Valli、Fengjiun Kuo

  DOI：10.1002/jlcr.956

  日期：2005.7

  As part of a program aimed at the design of conformationally constrained analogs of glutamic acid, (+)-2-aminobicyclo[3.1.0]hexane-2,6-carboxylic acid (1), identified as a highly potent, selective, group II metabotropic glutamate receptor agonist has been synthesized and studied clinically. Heterocyclic analogs of 1 were subsequently synthesized in which the C-2 methylene has been replaced by an oxygen atom (2) or a sulfur atom (3). C-14 labeled isotopomers of 1, 2 and 3 have been synthesized to facilitate pre-clinical ADME studies. A tritium labeled isotopomer of 1 was also synthesized for use in in vitro experiments. A stable labeled isotopomer of rac-1 was prepared for use as an internal standard for bioanalytical assays. The key step in each of these syntheses was the reaction of chiral ketone 4, 5 or 6 with K14CN/(NH4)2CO3 using the Bucherer–Berg protocol. In the preparation of the stable labeled isotopomer, rac-4-[13C2] was prepared in two steps from ethyl bromoacetate-[UL-13C2]; subsequent reaction of rac-4-[13C2] with K13CN/15NH4Cl/Na2CO3, followed by hydrolysis of the hydantoin yielded rac-1-[13C3,15N]. Copyright © 2005 John Wiley & Sons, Ltd.

  作为旨在设计构象限制型谷氨酸类似物的项目的一部分，合成并临床研究了(+)-2-氨基双环[3.1.0]己烷-2,6-羧酸（1），该化合物被确定为一种高度有效、选择性的二类代谢型谷氨酸受体激动剂。随后合成了1的杂环类似物，其中C-2亚甲基被氧原子（2）或硫原子（3）取代。合成了1、2和3的C-14标记同位素，以方便进行临床前的ADME研究。还合成了1的氚标记同位素，用于体外实验。为生物分析检测准备了稳定的标记同位素rac-1作为内标。这些合成中的关键步骤是手性酮4、5或6与K14CN/(NH4)2CO3的反应，采用Bucherer–Berg协议。在稳定标记同位素的制备中，rac-4-[13C2]是通过从乙基溴乙酸酯-[UL-13C2]的两步反应制得的；随后将rac-4-[13C2]与K13CN/15NH4Cl/Na2CO3反应，接着进行酰脲的水解，最终得到rac-1-[13C3,15N]。版权 © 2005 John Wiley & Sons, Ltd.
• Excitatory amino acid receptor antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0774455A1

  公开（公告）日：1997-05-21

  Compounds of the formula    in which X represents a bond, S, O or NRa; and R is as defined in the specification are useful as modulators of metabotropic glutamate receptor function.

  式子为    的化合物，其中X代表键合、S、O或NRa；而R则如规范所定义的，可作为代谢型谷氨酸受体功能调节剂。
• PRODRUGS OF EXCITATORY AMINO ACIDS
  申请人：Moher Eric David

  公开号：US20080182889A1

  公开（公告）日：2008-07-31

  This invention relates to synthetic excitatory amino acid prodrugs and processes for their preparation. The invention further relates to methods of using, and pharmaceutical compositions comprising, the compounds for the treatment of neurological disorders and psychiatric disorders.

  本发明涉及合成兴奋性氨基酸前药及其制备方法。本发明还涉及使用该化合物治疗神经系统疾病和精神障碍的方法和包含该化合物的药物组合物。