dimethyl (2S,4R)-1-benzyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2,4-dicarboxylate | 911697-27-3

• 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: dimethyl (2S,4R)-1-benzyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2,4-dicarboxylate
• CAS: 911697-27-3
• 化学式: C₂₀H₂₈N₂O₆
• 分子量: 392.452
• InChiKey: AIHLIBXBYLEEBP-MGPUTAFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (2S,4R)-1-benzyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2,4-dicarboxylate 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 生成 dimethyl (2S,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist

  摘要：

  A new family of mGlu receptor orthosteric ligands called APTCs was designed and synthesized using a parallel chemistry approach. Amongst 65 molecules tested on mGlu4, mGlu6 and mGlu8 subtypes, (2S,4S)-4-amino-1-[(E)-3-carboxyacryloyl]pyrrolidine-2,4-dicarboxylic acid (8a06-FP0429) has been shown to be a full mGlu4 agonist and a partial mGlu8 agonist. In addition, 8a06 was shown to be selective versus group I and II mGlu subtypes. A possible explanation for this efficacy difference is proposed by docking experiment performed with molecular model of the receptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.062
• 作为产物：
  描述：

  ethyl (2S)-1-benzyl-4-oxoprolinate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 dimethyl (2S,4R)-1-benzyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist

  摘要：

  A new family of mGlu receptor orthosteric ligands called APTCs was designed and synthesized using a parallel chemistry approach. Amongst 65 molecules tested on mGlu4, mGlu6 and mGlu8 subtypes, (2S,4S)-4-amino-1-[(E)-3-carboxyacryloyl]pyrrolidine-2,4-dicarboxylic acid (8a06-FP0429) has been shown to be a full mGlu4 agonist and a partial mGlu8 agonist. In addition, 8a06 was shown to be selective versus group I and II mGlu subtypes. A possible explanation for this efficacy difference is proposed by docking experiment performed with molecular model of the receptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.062

文献信息

• [EN] CIS PYRROLIDINYL DERIVATIVES AND THEIR USES<br/>[FR] DERIVES DE CIS PYRROLIDINYLE ET LEURS UTILISATIONS
  申请人：FAUST PHARMACEUTICALS

  公开号：WO2005118534A1

  公开（公告）日：2005-12-15

  The present invention provides new cis pyrrolidinyl of the formula (I) or (II) in which: R1, R2 or R3 are hydrogen or a carboxy or amino protecting group; R4 to R8 represent hydrogen or an alkyl radical; R9 represents a (R10)n,(-R11)m group wherein R10 is -CO-, -CS-, -O-, -S-, -SO-, -SO2-, -COO-, -CONRa-, -N(Ra)CO-, -CSNRa-, -N(Ra)CS-, -N(Ra)-, Rb, aryl, and R11 is a polar group, and their use for the treatment and/or prophylaxis of a condition associated with altered glutamatergic signalling and/or functions, and/or conditions which can be affected by alteration of glutamate level or signalling.
• Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist
  作者：Stephan Schann、Christel Menet、Paul Arvault、Géraldine Mercier、Mélanie Frauli、Stanislas Mayer、Nadia Hubert、Nicolas Triballeau、Hugues-Olivier Bertrand、Francine Acher、Pascal Neuville

  DOI：10.1016/j.bmcl.2006.06.062

  日期：2006.9

  A new family of mGlu receptor orthosteric ligands called APTCs was designed and synthesized using a parallel chemistry approach. Amongst 65 molecules tested on mGlu4, mGlu6 and mGlu8 subtypes, (2S,4S)-4-amino-1-[(E)-3-carboxyacryloyl]pyrrolidine-2,4-dicarboxylic acid (8a06-FP0429) has been shown to be a full mGlu4 agonist and a partial mGlu8 agonist. In addition, 8a06 was shown to be selective versus group I and II mGlu subtypes. A possible explanation for this efficacy difference is proposed by docking experiment performed with molecular model of the receptor. (c) 2006 Elsevier Ltd. All rights reserved.