N-(乙氧羰基)-D-丙氨酸 | 148731-47-9

• 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
• 中文名称: N-(乙氧羰基)-D-丙氨酸
• 英文名称: (R)-N-carbethoxy-2-aminopropanoic acid
• 英文别名: N-(ethoxycarbonyl)alanine；(-)-N-β-Carboxyethyl-D-alanin；(R)-(N-ethoxycarbonyl)alanine；(R)-2-((Ethoxycarbonyl)amino)propanoic acid；(2R)-2-(ethoxycarbonylamino)propanoic acid
• CAS: 148731-47-9
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: JYQWKPMPTMJFCY-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(乙氧羰基)-D-丙氨酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 ethyl (1-oxo-1-(p-tolyl)propan-2-yl)carbamate
  参考文献：
  名称：

  Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters

  摘要：

  Background and Purpose4‐Methyl‐N‐methylcathinone (mephedrone) is a synthetic stimulant that acts as a substrate‐type releaser at transporters for dopamine (DAT), noradrenaline (NET) and 5‐HT (SERT). Upon systemic administration, mephedrone is metabolized to several phase I compounds: the N‐demethylated metabolite, 4‐methylcathinone (nor‐mephedrone); the ring‐hydroxylated metabolite, 4‐hydroxytolylmephedrone (4‐OH‐mephedrone); and the reduced keto‐metabolite, dihydromephedrone.Experimental ApproachWe used in vitro assays to compare the effects of mephedrone and synthetically prepared metabolites on transporter‐mediated uptake and release in HEK293 cells expressing human monoamine transporters and in rat brain synaptosomes. In vivo microdialysis was employed to examine the effects of i.v. metabolite injection (1 and 3 mg·kg−1) on extracellular dopamine and 5‐HT levels in rat nucleus accumbens.Key ResultsIn cells expressing transporters, mephedrone and its metabolites inhibited uptake, although dihydromephedrone was weak overall. In cells and synaptosomes, nor‐mephedrone and 4‐OH‐mephedrone served as transportable substrates, inducing release via monoamine transporters. When administered to rats, mephedrone and nor‐mephedrone produced elevations in extracellular dopamine and 5‐HT, whereas 4‐OH‐mephedrone did not. Mephedrone and nor‐mephedrone, but not 4‐OH‐mephedrone, induced locomotor activity.Conclusions and ImplicationsOur results demonstrate that phase I metabolites of mephedrone are transporter substrates (i.e. releasers) at DAT, NET and SERT, but dihydromephedrone is weak in this regard. When administered in vivo, nor‐mephedrone increases extracellular dopamine and 5‐HT in the brain whereas 4‐OH‐mephedrone does not, suggesting the latter metabolite does not penetrate the blood–brain barrier. Future studies should examine the pharmacokinetics of nor‐mephedrone to determine its possible contribution to the in vivo effects produced by mephedrone.

  DOI：

  10.1111/bph.13547
• 作为产物：
  描述：

  D-丙氨酸 、 氯甲酸乙酯 在 碳酸氢钠 作用下， 生成 N-(乙氧羰基)-D-丙氨酸
  参考文献：
  名称：

  ‘One-Pot’ Synthesis of Chiral N-Protected α-Amino Acid-Derived 1,2,4-Oxadiazoles

  摘要：

  一系列α-氨基酸衍生的1,2,4-噁二唑通过一种简单、廉价的一锅法合成。该杂环化合物的产率良好，反应时间相对较短。

  DOI：

  10.1055/s-2004-822391

文献信息

• PROCESS FOR THE PREPARATION OF INDOLINE DERIVATIVES AND THEIR INTERMEDIATES THEREOF
  申请人：Joshi Shreerang

  公开号：US20120165548A1

  公开（公告）日：2012-06-28

  Processes for the preparation of Silodosin and its intermediates comprising reductive amination of compound of Formula (VIII) with a compound of Formula (VII) or a compound of Formula (XV) in a suitable solvent using a reducing agent.

  制备Silodosin及其中间体的过程包括在适当溶剂中使用还原剂将化合物(VIII)的化合物与化合物(VII)或化合物(XV)进行还原胺化。
• Peptidartige Aminosäurederivate
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0310918A2

  公开（公告）日：1989-04-12

  Verbindung der Formel worin R1, R2, R3, R4 und A die in Anspruch 1 angegebene Bedeutung haben, sowie pharmazeutisch verwendbare Salze davon besitzen Renin-inhibierende Eigenschaften und können demnach in Form pharmazeutischer Präparate als Arzneimittel verwendet werden. Sie können nach an sich bekannten Methoden hergestellt werden.

  式中的化合物 其中 R1、R2、R3、R4 和 A 具有权利要求 1 中给出的含义，其药用盐具有抑制肾素的特性，因此可以以药物制剂的形式用作药物。它们可以通过本身已知的方法制备。
• [EN] PROCESS FOR THE PREPARATION OF INDOLINE DERIVATIVES AND THEIR INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS D'INDOLINE ET LEURS INTERMÉDIAIRES
  申请人：SANDOZ AG

  公开号：WO2011030356A3

  公开（公告）日：2011-05-05
• Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl) propane]dichloroplatinum(II) Complexes
  作者：Francois Dufrasne、Michael Gelbcke、Beate Schnurr、Ronald Gust

  DOI：10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q

  日期：2002.5

  Enantiomericaily pure 1,2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R,2S)- and (1S,2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by H-1 NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl2 were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl2 even in a concentration of 1 muM. The (1S,2R)- and (1R,2S)-configurated complexes were far less active (SS>RR>RS=SR) and comparable in this respect with the standard cisplatin.
• WANG, CHIA-LIN J.;CALABRESE, JOSEPH C., J. ORG. CHEM., 56,(1991) N4, C. 4341-4343
  作者：WANG, CHIA-LIN J.、CALABRESE, JOSEPH C.

  DOI：——

  日期：——