3-氨基-2-(3,4-二甲氧基苯基)丙酸乙酯 | 56003-06-6

• 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
• 中文名称: 3-氨基-2-(3,4-二甲氧基苯基)丙酸乙酯
• 英文名称: ethyl 3-amino-2-(3,4-dimethoxyphenyl)propanoate
• 英文别名: α-(aminomethyl)-3,4-dimethoxybenzeneacetic acid ethyl ester；3-amino-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester；3-Amino-2-<3,4-dimethoxy-phenyl>-propionsaeure-ethylester；3-Amino-2-(3,4-dimethoxy-phenyl)-propionsaeure-aethylester；3-Amino-2-(3,4-dimethoxy-phenyl)-propionsaeure-ethylester
• CAS: 56003-06-6
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: SVBYEXVSRYCLDO-UHFFFAOYSA-N

物化性质

• 沸点：
  370.0±42.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  3-氨基-2-(3,4-二甲氧基苯基)丙酸乙酯 在 五氯化磷 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 sulfur 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 1-[Hydroxy-(3-methoxyphenyl)methyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid
  参考文献：
  名称：

  Discovery of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors

  摘要：

  Through high throughput screening and subsequent hit identification and optimization, we synthesized a series of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as the first reported potent and reversible GFAT inhibitors. SAR studies of this class of compounds indicated significant impact on GFAT inhibition potency by substitutions on the A-ring and C-ring. The ketone group was found to be necessary for high potency. Compound 28 (RO0509347) demonstrated potent GFAT inhibition (IC(50) = 1 mu M) with a desirable pharmacokinetic profile in rats, and showed significant efficacy in reducing the glucose excursion in an OGTT test in ob/ob mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.009
• 作为产物：
  描述：

  3,4-二甲氧基苯乙腈 在 盐酸 、 palladium on activated charcoal 、 氢气 、 sodium 作用下， 以 乙醇 、 甲苯 为溶剂， 80.0 ℃ 、344.75 kPa 条件下， 生成 3-氨基-2-(3,4-二甲氧基苯基)丙酸乙酯
  参考文献：
  名称：

  Discovery of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors

  摘要：

  Through high throughput screening and subsequent hit identification and optimization, we synthesized a series of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as the first reported potent and reversible GFAT inhibitors. SAR studies of this class of compounds indicated significant impact on GFAT inhibition potency by substitutions on the A-ring and C-ring. The ketone group was found to be necessary for high potency. Compound 28 (RO0509347) demonstrated potent GFAT inhibition (IC(50) = 1 mu M) with a desirable pharmacokinetic profile in rats, and showed significant efficacy in reducing the glucose excursion in an OGTT test in ob/ob mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.009

文献信息

• Synthesis of Substituted Isoquinolines <i>via</i> Pd-Catalyzed Cross-Coupling Approaches
  作者：Nick Todorovic、Emelia Awuah、Silvia Albu、Cory Ozimok、Alfredo Capretta

  DOI：10.1021/ol202565j

  日期：2011.12.2

  arylation of ethyl cyanoacetate, malononitrile, and various ketones. The products from these reactions can be elaborated to substituted β-arylethylamines and used in microwave-assisted Pictet–Spengler reactions. The protocol developed is suitable for the synthesis of libraries of substituted isoquinolines.

  掺入基于1,3,5,7-四甲基-2,4,8-三氧杂-6-磷金刚烷骨架的配体的钯络合物用于催化氰基乙酸乙酯，丙二腈和各种酮的芳基化。这些反应的产物可以精制为取代的β-芳基乙胺，并用于微波辅助的Pictet-Spengler反应。开发的协议适用于取代异喹啉文库的合成。
• Glutamine fructose-y-phosphate amidotransferase (GFAT) inhibitors
  申请人：——

  公开号：US20040259910A1

  公开（公告）日：2004-12-23

  Compounds of formula I are provided 1 as well as pharmaceutically acceptable salts and esters thereof, wherein the substituents are as disclosed in the specification. The compounds have utility for the treatment of type 2 diabetes mellitus.

  提供了化学式I的化合物，以及其药学上可接受的盐和酯，其中取代基如规范中所披露。这些化合物可用于治疗2型糖尿病。
• [EN] ISOQUINOLINE DERIVATIVES AND THEIR USE AS GFAT INHIBITORS<br/>[FR] INHIBITEURS DE LA GFAT
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004101528A3

  公开（公告）日：2005-01-06
• ISOQUINOLINE DERIVATIVES AND THEIR USE AS GFAT INHIBITORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1631551A2

  公开（公告）日：2006-03-08
• US4544657A
  申请人：——

  公开号：US4544657A

  公开（公告）日：1985-10-01