methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate | 132431-11-9

• 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: methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate
• 英文别名: (R)-1-benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate；1-benzyl 2-methyl (R)-4-oxopyrrolidine-1,2-dicarboxylate；1-Benzyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate；1-O-benzyl 2-O-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate
• CAS: 132431-11-9
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: XRFKZAWVKVORNI-GFCCVEGCSA-N

物化性质

• 沸点：
  422.1±45.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 甲酸 、 三正丁胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (R)-1-benzyl 2-methyl 1H-pyrrole-1,2(2H,5H)-dicarboxylate
  参考文献：
  名称：

  [EN] PYRROLIDINE GPR40 MODULATORS
  [FR] MODULATEURS PYRROLIDINES DE GPR40

  摘要：

  本发明提供了式(I)的化合物：或其立体异构体，或其药物可接受的盐，其中所有变量均如本文所述定义。这些化合物是GPR40 G蛋白偶联受体的调节剂，可用作药物。

  公开号：

  WO2014078609A1
• 作为产物：
  描述：

  N-CBZ-顺式-4-羟基-D-脯氨酸甲酯 在 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以76%的产率得到methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  [EN] PYRROLIDINE GPR40 MODULATORS FOR THE TREATMENT OF DISEASES SUCH AS DIABETES
  [FR] COMPOSÉS PYRROLIDINE MODULATEURS DE GPR40 POUR LE TRAITEMENT DE MALADIES TELLES QUE LE DIABÈTE

  摘要：

  本发明提供了式（I）的化合物或其立体异构体、互变异构体、药学上可接受的盐、多型体或溶剂化合物，其中所有变量均如本文所定义。这些化合物是GPR40 G蛋白偶联受体调节剂，可用作药物。

  公开号：

  WO2015171722A1

文献信息

• [EN] PYRROLIDINE GPR40 MODULATORS<br/>[FR] MODULATEURS DE GPR40 À BASE DE PYRROLIDINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015171757A1

  公开（公告）日：2015-11-12

  The present invention provides compounds of Formula (I): or a stereoisomer, a tautomer, a pharmaceutically acceptable salt, a polymorph, or a solvate thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

  本发明提供了式(I)的化合物：或其立体异构体、互变异构体、药用盐、多晶型或溶剂化物，其中所有变量均如本文所述定义。这些化合物是GPR40 G蛋白偶联受体的调节剂，可用作药物。
• Compounds for the treatment of inflammatory disorders
  申请人：Siddiqui Arshad M.

  公开号：US20060178366A1

  公开（公告）日：2006-08-10

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, aggrecanase, ADMP, LpxC, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及式（I）的化合物：或其药学上可接受的盐、溶剂或异构体，可用于治疗由MMPs、aggrecanase、ADMP、LpxC、ADAMs、TACE、TNF-α或其组合介导的疾病或病况。
• Compounds for the treatment of inflammatory disorders and microbial diseases
  申请人：Siddiqui Arshad M.

  公开号：US20070167426A1

  公开（公告）日：2007-07-19

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, aggrecanase, ADMP, LpxC, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及式(I)的化合物：或其药学上可接受的盐、溶剂或异构体，可用于治疗由MMPs、aggrecanase、ADMP、LpxC、ADAMs、TACE、TNF-α或其组合介导的疾病或病况。
• COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS
  申请人：Guo Zhuyan

  公开号：US20100145048A1

  公开（公告）日：2010-06-10

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, ADAMs, TACE, TNF-α or combinations thereof.

  本发明涉及公式(I)的化合物：或其药学上可接受的盐、溶剂化合物或异构体，可用于治疗由MMPs、ADAMs、TACE、TNF-α或其组合介导的疾病或病症。
• Synthesis and biological evaluation of 4-hydroxy-4-(4-methoxyphenyl)-substituted proline and pyrrolidin-2-ylacetic acid derivatives as GABA uptake inhibitors
  作者：Xueqing Zhao、Jörg Pabel、Georg C. Höfner、Klaus T. Wanner

  DOI：10.1016/j.bmc.2012.11.015

  日期：2013.1

  A series of enantiomerically pure 4-hydroxy-4-(4-methoxyphenyl)-substituted proline and pyrrolidin-2-ylacetic acid derivatives have been synthesized starting from the respective N-protected 4-hydroxy derivatives via oxidation to the corresponding 4-oxo compounds, subsequent addition of organometallic reagents, final hydrolysis and deprotection. The major diastereoisomers obtained by the addition of the Grignard reagents were found to have opposite stereoconfigurations depending on whether cerium trichloride was present or absent as an additive. The final compounds were evaluated for their capability to inhibit the GABA transport proteins GAT1 and GAT3. 4-Hydroxyproline derivatives substituted with a tris(4-methoxyphenyl)methyloxyethyl residue at the nitrogen and a 4-methoxyphenyl group in 4-position showed, with the exception of the (2R,4R)-diastereomer, an improved inhibition at GAT3 compared to the derivatives missing the 4-methoxyphenyl group in 4-position. This may imply that an appropriate lipophilic group at the C-4 position of the proline moiety is beneficial for potent inhibition at GAT3. (C) 2012 Elsevier Ltd. All rights reserved.