(2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine | 130930-27-7

• 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: (2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine
• 英文别名: N-(benzyloxycarbonyl)-cis-4-hydroxy-D-proline ethyl ester；N-Cbz-cis-4-hydroxy-D-proline ethyl ester；ethyl (2R,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate；(2R,4R)-N-benzyloxycarbonyl-2-ethoxycarbonyl-4-hydroxy pyrrolidine；1-Benzyl 2-ethyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate；1-O-benzyl 2-O-ethyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 130930-27-7
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: FEPRPINUVNZMRY-CHWSQXEVSA-N

物化性质

• 沸点：
  434.1±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine 在 吡啶 、 盐酸 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 268.0h， 生成 N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester
  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
• 作为产物：
  描述：

  顺式-4-羟基-D-脯氨酸 在 氯化亚砜 、 magnesium sulfate 、 三乙胺 、 柠檬酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 20.0h， 生成 (2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Thrombin Inhibitors from the Freshwater Cyanobacterium Anabaena compacta

  摘要：

  Bioassay-guided investigation of the cyanobacterium Anabaena compacta extracts afforded spumigin J (1) and the known thrombin inhibitor spumigin A (2). The absolute configuration of 1 was analyzed by advanced Marfey's methodology. Compounds 1 and 2 inhibited thrombin with EC50 values of 4.9 and 2.1 mu M, and 0.7 and 0.2 mu M in the cathepsin B inhibitory assay, respectively. The MM-GBSA methodology predicted spumigin A with 2S-4-methylproline as the better thrombin inhibitor.

  DOI：

  10.1021/np300282a

文献信息

• RNA-selective cross-pairing of backbone-extended pyrrolidine-amideoligonucleotide mimics (bePOMs)
  作者：Roberta J. Worthington、Neil M. Bell、Raymond Wong、Jason Micklefield

  DOI：10.1039/b714580m

  日期：——

  Pyrrolidine-amide oligonucleotide mimics (POMs) can cross-pair strongly with complementary parallel and antiparallel DNA and RNA targets in a sequence-specific fashion. As a result POMs have significant potential for applications including in vivogene silencing, diagnostics and bioanalysis. To further modulate the DNA- and RNA-recognition properties and fine-tune the physiochemical properties of POMs for nucleic acid targeting, backbone-extended pyrrolidine-amideoligonucleotide mimics (bePOM I and II) were introduced. The bePOMs differ from the original POMs through the insertion of an additional methylene group into the backbone units, which increases the flexibility of the oligomers. bePOM I and II oligomers were synthesised using solid-phase peptide chemistry. Interestingly, UV thermal denaturation and circular dichroism studies reveals bePOM I and II can hybridise with complementary RNA, but not DNA.

  吡咯烷-酰胺低聚核苷酸模拟物（POMs）能够与互补的平行和反平行DNA及RNA靶标以序列特异性的方式强烈配对。因此，POMs在基因沉默、诊断和生物分析等应用方面具有显著的潜力。为了进一步调节POMs对DNA和RNA的识别特性，并微调其物理化学性质以实现核酸靶向，我们引入了骨架扩展的吡咯烷-酰胺低聚核苷酸模拟物（bePOM I和II）。bePOMs通过在骨架单元中插入一个额外的亚甲基，从而增加了寡聚物的柔韧性，与原始POMs有所不同。bePOM I和II寡聚物是通过固相肽化学合成制备的。有趣的是，紫外热变性和圆二色性研究表明，bePOM I和II能够与互补RNA杂交，但不能与DNA杂交。
• Pyrrolidinyl di-carboxylic acid derivatives as metabotropic glutamate
  申请人：Eli Lilly and Company

  公开号：US05473077A1

  公开（公告）日：1995-12-05

  The present invention provides novel compounds that affect certain excitatory amino acid receptors, and are useful in the treatment of neurological disorders and psychiatric disorders.

  本发明提供了影响某些兴奋性氨基酸受体的新化合物，可用于治疗神经系统疾病和精神疾病。
• Benzamide derivatives
  申请人：Teikoku Chemical Industry Co., Ltd.

  公开号：US05143935A1

  公开（公告）日：1992-09-01

  A benzamide derivative represented by the formula: ##STR1## having a promoting activity of gastrointestinal tract and pharmacentical composition containing the same.

  由以下公式表示的苯甲酰胺衍生物：##STR1## 具有促进胃肠道活性的药物成分及包含相同成分的药物组合物。
• Method of inhibiting the transport of L-glutamate to treat CNS disorders
  申请人：The Regents of the University of California

  公开号：US05942537A1

  公开（公告）日：1999-08-24

  A method of inhibiting the transport of a neurotransmitter away from the synapse comprising contacting a neurotransmitter transporter with a compound having the structure ##STR1## wherein ##STR2## or CONHR.sup.3 in any combination and and wherein R.sup.2 =OR.sup.3, NR.sup.3.sub.2, alkyl, or substituted alkyl and R.sup.3 =alkyl or substituted alkyl.

  一种抑制神经递质从突触运输的方法，包括将具有以下结构的化合物与神经递质转运体接触：##STR1## 其中 ##STR2## 或 CONHR.sup.3 以任意组合方式出现，其中 R.sup.2 =OR.sup.3、NR.sup.3.sub.2、烷基或取代烷基，R.sup.3 =烷基或取代烷基。
• 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