N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycine | 1003958-92-6

• 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: N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycine
• 英文别名: 2-[3,4-dichloro-N-(2-methoxyethyl)anilino]acetic acid
• CAS: 1003958-92-6
• 化学式: C₁₁H₁₃Cl₂NO₃
• 分子量: 278.135
• InChiKey: CPKSXEXLCBIVAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-溴苯基)-N-甲基-2-(吡咯烷-1-基)乙烷-1-胺 、 N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N1-[1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]-N2-(3,4-dichlorophenyl)-N1-methyl-N2-[2-(methyloxy)ethyl]glycinamide
  参考文献：
  名称：

  Potent and selective small-molecule human urotensin-II antagonists with improved pharmacokinetic profiles

  摘要：

  Lead compound 1 was successfully redesigned to provide compounds with improved pharmacokinetic profiles for this series of human urotensin-II antagonists. Replacement of the 2-pyrrolidinylmethyl-3-phenyl-piperidine core of 1 with a substituted N-methyl-2-(1-pyrrolidinyl) ethanamine core as in compound 7 resulted in compounds with improved oral bioavailability in rats. The relationship between stereochemistry and selectivity for hUT over the kappa-opioid receptor was also explored. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.058
• 作为产物：
  描述：

  ethyl N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycinate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycine
  参考文献：
  名称：

  Development of potent and selective small-molecule human Urotensin-II antagonists

  摘要：

  This work describes the development of potent and selective human Urotensin-II receptor antagonists starting from lead compound 1, (3,4-dichlorophenyl) methyl{2-oxo-2-[3-phenyl-2-(1-pyrrolidinylmethyl)1-piperidinyl]ethyl}amine. Several problems relating to oral bioavailability, cytochrome P450 inhibition, and off-target activity at the kappa opioid receptor and cardiac sodium channel were addressed during lead development. hUT binding affinity relative to compound 1 was improved by more than 40-fold in some analogs, and a structural modi. cation was identified which significantly attenuated both off-target activities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.027

文献信息

• MORPHOLINYL AND PYRROLIDINYL ANALOGS
  申请人：Goodman Krista B.

  公开号：US20080021023A1

  公开（公告）日：2008-01-24

  The present invention relates to morpholinyl, and pyrrolidinyl analogs, pharmaceutical compositions containing them, and their use as antagonists of urotensin II.

  本发明涉及吗吗啉基和吡咯啉基类似物，含有它们的药物组合物，以及它们作为尿苷II拮抗剂的用途。
• Morpholinyl and pyrrolidinyl analogs
  申请人：GlaxoSmithKline LLC

  公开号：US07749998B2

  公开（公告）日：2010-07-06

  The present invention relates to morpholinyl, and pyrrolidinyl analogs, pharmaceutical compositions containing them, and their use as antagonists of urotensin II.

  本发明涉及吗啡啶基和吡咯烷基类似物，含有它们的制药组合物，以及它们作为尿加压素II拮抗剂的用途。
• US7432258B2
  申请人：——

  公开号：US7432258B2

  公开（公告）日：2008-10-07
• US7749998B2
  申请人：——

  公开号：US7749998B2

  公开（公告）日：2010-07-06
• [EN] MORPHOLINYL AND PYRROLIDINYL ANALOGS<br/>[FR] ANALOGUES DE MORPHOLINYLE ET DE PYRROLIDINYLE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2008011551A1

  公开（公告）日：2008-01-24

  [EN] The present invention relates to morpholinyl, and pyrrolidinyl analogs, pharmaceutical compositions containing them, and their use as antagonists of urotensin II.
  [FR] La présente invention concerne des analogues de morpholinyle et de pyrrolidinyle, des compositions pharmaceutiques les contenant et leur utilisation comme antagonistes de l'urotensine II.