(S)-alpha-Amino-4-methoxy-alpha-methylbenzeneacetic Acid, Ethyl Ester | 170689-16-4

• 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: (S)-alpha-Amino-4-methoxy-alpha-methylbenzeneacetic Acid, Ethyl Ester
• 英文别名: ethyl (2S)-2-amino-2-(4-methoxyphenyl)propanoate
• CAS: 170689-16-4
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: GCEUEDWPJDYEBS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-alpha-Amino-4-methoxy-alpha-methylbenzeneacetic Acid, Ethyl Ester 在 palladium on activated charcoal 氟化铵 、 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二乙二醇二甲醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-N-(2-chlorophenyl)-2-[[(2R)-2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]-2-(4-methoxyphenyl)propanamide
  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：

  5-(P-甲氧基苯基)-5-甲基海因 在 盐酸 、 sodium hydroxide 作用下， 生成 (S)-alpha-Amino-4-methoxy-alpha-methylbenzeneacetic Acid, Ethyl Ester
  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

• Catecholamine surrogates useful as .beta..sub.3 agonists
  申请人：Bristol-Myers Squibb Company

  公开号：US05770615A1

  公开（公告）日：1998-06-23

  Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof. These compounds are beta three adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

  公式为##STR1##的化合物及其药学上可接受的盐。这些化合物是β三肾上腺素受体激动剂，因此在糖尿病、肥胖症和胃肠疾病的治疗中是有用的。
• IMIDAZOLIDINE DERIVATIVES, USES THEREFOR, PREPARATION THEREOF AND COMPOSITIONS COMPRISING SUCH
  申请人：Galapagos SAS

  公开号：EP2026799B1

  公开（公告）日：2011-06-22
• US8168667B2
  申请人：——

  公开号：US8168667B2

  公开（公告）日：2012-05-01
• BMS-201620: a selective beta 3 agonist
  作者：W.N. Washburn、C.-Q. Sun、G. Bisacchi、G. Wu、P.T. Cheng、P.M. Sher、D. Ryono、A.V. Gavai、K. Poss、R.N. Girotra、P.J. McCann、A.B. Mikkilineni、T.C. Dejneka、T.C. Wang、Z. Merchant、M. Morella、C.M. Arbeeny、T.W. Harper、D.A. Slusarchyk、S. Skwish、A.D. Russell、G.T. Allen、B. Tesfamariam、B.H. Frohlich、B.E. Abboa-Offei、M. Cap、T.L. Waldron、R.J. George、D. Young、K.E. Dickinson、A.A. Seymour

  DOI：10.1016/j.bmcl.2004.04.074

  日期：2004.7

  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.