R-alpha-氨基-4-甲氧基苯乙酰胺 | 67412-96-8

• 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: R-alpha-氨基-4-甲氧基苯乙酰胺
• 英文名称: D-(-)-4-methoxyphenylglycine amide
• 英文别名: D-p-methoxyphenylglycine amide；(R)-2-amino-2-(4-methoxyphenyl)acetamide；(2R)-2-amino-2-(4-methoxyphenyl)acetamide
• CAS: 67412-96-8
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: TZADAWVLFGIAKY-MRVPVSSYSA-N

物化性质

• 沸点：
  371.2±42.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  R-alpha-氨基-4-甲氧基苯乙酰胺 在 钯 氟化铵 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R)-2-[[(2R)-2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]-2-(4-methoxyphenyl)acetamide
  参考文献：
  名称：

  BMS-201620: a selective beta 3 agonist

  摘要：

  A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent beta(3) full agonist (K-i = 93 nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.074
• 作为产物：
  描述：

  (R)-(N-benzyloxycarbonyl)-p-methoxyphenylglycine 在 palladium dihydroxide 氨 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 R-alpha-氨基-4-甲氧基苯乙酰胺
  参考文献：
  名称：

  BMS-201620: a selective beta 3 agonist

  摘要：

  A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human beta(3) adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent beta(3) full agonist (K-i = 93 nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.074

文献信息

• Practical and Convenient Enzymatic Synthesis of Enantiopure α-Amino Acids and Amides
  作者：Mei-Xiang Wang、Shuang-Jun Lin

  DOI：10.1021/jo0256282

  日期：2002.9.1

  enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of D-(-)-alpha-phenylglycine amide, biotransformation of DL-phenylglycine nitrile was applied in practical scale to produce both D- and L-phenylglycines in high optical purity.

  在红球菌属中被腈水合酶和酰胺酶催化。AJ270细胞在非常温和的条件下，许多α-芳基-和α-烷基取代的DL-甘氨酸腈1迅速经历高度对映选择性水解，从而得到D-（-）-α-氨基酸酰胺2和L-（+ ）-α-氨基酸3的收率很高，多数情况下对映异构体过量。腈类生物转化的总体对映选择性源于高L-对映选择性酰胺酶和低对映选择性腈水合酶的综合作用。还在空间和电子效应方面讨论了底物对反应效率和对映选择性的影响。加上D-（-）-α-苯基甘氨酸酰胺的化学水解，
• KV1.5 POTASSIUM CHANNEL INHIBITORS
  申请人：Janusz Michael John

  公开号：US20070299120A1

  公开（公告）日：2007-12-27

  The present invention relates to 1-N-amino-2-imidazolidinones and derivatives thereof which are effective as Kv1.5 potassium channel inhibitors providing atrial-selective antiarrhythmic agents. The present invention further relates to compositions comprising said Kv1.5 potassium channel inhibitors, and to methods for treating cardiac arrhythmia.

  本发明涉及1-N-氨基-2-咪唑啉酮及其衍生物，其作为Kv1.5钾通道抑制剂，提供房颤选择性抗心律失常药物。本发明还涉及含有上述Kv1.5钾通道抑制剂的组合物，以及治疗心律失常的方法。
• Highly efficient and enantioselective synthesis of l-arylglycines and d-arylglycine amides from biotransformations of nitriles
  作者：Mei-Xiang Wang、Shuang-Jun Lin

  DOI：10.1016/s0040-4039(01)01439-3

  日期：2001.9

  Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active d-arylglycine amides 2 and l-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

  在非常温和的条件下，红球菌属。由取代的苯甲醛，氯化铵和氰化钾的反应轻松制备的AJ270催化的芳基甘氨酸腈1的生物转化可有效地以优异的收率生产光学活性的d-芳基甘氨酸酰胺2和l-芳基甘氨酸3，对映体过量率高于99％ 。
• Kv1.5 potassium channel inhibitors
  申请人：Wyeth

  公开号：US07504517B2

  公开（公告）日：2009-03-17

  The present invention relates to 1-N-amino-2-imidazolidinones and derivatives thereof which are effective as Kv1.5 potassium channel inhibitors providing atrial-selective antiarrhythmic agents. The present invention further relates to compositions comprising said Kv1.5 potassium channel inhibitors, and to methods for treating cardiac arrhythmia.

  本发明涉及1-N-氨基-2-咪唑烷酮及其衍生物，其作为Kv1.5钾通道抑制剂，提供心房选择性抗心律失常剂。本发明还涉及包含上述Kv1.5钾通道抑制剂的组合物，以及治疗心律失常的方法。
• Lopata, Antal; Faigl, Ferenc; Fogassy, Elemer, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2930 - 2952
  作者：Lopata, Antal、Faigl, Ferenc、Fogassy, Elemer、Darvas, Ferenc

  DOI：——

  日期：——