(2R,4S)-2,4-吡咯烷二甲酸 | 130830-77-2

• 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
• 中文名称: (2R,4S)-2,4-吡咯烷二甲酸
• 英文名称: D-trans-2,4-PDC
• 英文别名: trans-4-carboxy-D-proline；(2R,4S)-4-carboxypyrrolidin-1-ium-2-carboxylate
• CAS: 130830-77-2
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: NRSBQSJHFYZIPH-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 二甲基亚砜 为溶剂， 25.0~80.0 ℃ 、344.73 kPa 条件下， 反应 269.42h， 生成 (2R,4S)-2,4-吡咯烷二甲酸
  参考文献：
  名称：

  Conformationally defined neurotransmitter analogs. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer

  摘要：

  In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared. These ''conformer mimics'', the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of [H-3]-L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites. While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport. These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.

  DOI：

  10.1021/jm00106a037

文献信息

• An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles
  作者：Raymond CF Jones、Kevin J Howard、John S Snaith

  DOI：10.1016/0040-4039(96)00114-1

  日期：1996.3

  Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral imidazolinium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g. naturally occurring proline derivatives and homochiral pyrrolizidines.

  从旋光性吡咯并咪唑类化合物中进行两步还原性去除，可以从同手性咪唑啉鎓基化物的1，3-偶极环加成中获得旋光性取代的吡咯烷类。取代基的选择性操纵提供了例如天然存在的脯氨酸衍生物和同手性吡咯并核苷。
• Beta-benzyloxyaspartate derivatives with amino group on benzene ring
  申请人：Shimamoto Keiko

  公开号：US20070238783A1

  公开（公告）日：2007-10-11

  L-threo-β-benzyloxyaspartate derivatives having a substituent on the benzene ring, represented by the following formula (1): wherein R is hydrogen, a linear or branched lower aliphatic acyl group with the acyl portion optionally substituted, an alicyclic acyl group, an aromatic acyl group with a substituent on the aromatic ring, an amino acid-derived group or a biotin derivative-derived group, having an amino substituent on the benzene ring, and salts thereof, which can easily bind to affinity column chromatography carriers as ligands of glutamate transporter proteins.

  具有苯环上取代基的L-单体-β-苄氧基天冬氨酸衍生物，化学式如下（1）：其中R为氢、具有酰基部分可选取代的线性或支链低级脂肪酰基、脂环酰基、苯环上具有取代基的芳香酰基、氨基酸衍生物基团或生物素衍生物基团，其在苯环上具有氨基取代基，以及其盐。该衍生物可以作为谷氨酸转运蛋白的配体，容易结合到亲和柱色谱载体上。
• Treatment of glial tumors with glutamate antagonists
  申请人：——

  公开号：US20030050224A1

  公开（公告）日：2003-03-13

  The present invention relates to a method of treating glial tumors in a subject, which includes providing a glutamate antagonist or a NMDA receptor antagonist and administering the glutamate antagonist or NMDA receptor antagonist to a subject with a glial tumor of the brain or spinal cord under conditions effective to treat the glial tumor.

  本发明涉及一种治疗受试者神经胶质瘤的方法，该方法包括提供谷氨酸拮抗剂或NMDA受体拮抗剂，并在有效治疗神经胶质瘤的条件下将谷氨酸拮抗剂或NMDA受体拮抗剂施用于患有脑或脊髓神经胶质瘤的受试者。
• BRIDGES, RICHARD J.;STANLEY, MARK S.;ANDERSON, MICHAEL W.;COTMAN, CARL W.+, J. MED. CHEM., 34,(1991) N, C. 717-725
  作者：BRIDGES, RICHARD J.、STANLEY, MARK S.、ANDERSON, MICHAEL W.、COTMAN, CARL W.+

  DOI：——

  日期：——
• METHOD OF INHIBITING THE TRANSPORT OF L-GLUTAMATE
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0497895A1

  公开（公告）日：1992-08-12