ethyl (+/-)-3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride | 54503-22-9

• 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
• 英文名称: ethyl (+/-)-3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride
• 英文别名: ethyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride；Ethyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate Hydrochloride；ethyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate;hydrochloride
• CAS: 54503-22-9
• 化学式: C₁₃H₁₉NO₄*ClH
• 分子量: 289.759
• InChiKey: APXOQZLYYZROMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  19
• 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：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (+/-)-3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 72.0h， 生成 (RS)-ethyl 3-(3,4-dimethoxyphenyl)-3-(5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)pentanamido)propanoate
  参考文献：
  名称：

  Structure Activity Relationships of α_v Integrin Antagonists for Pulmonary Fibrosis by Variation in Aryl Substituents

  摘要：

  Antagonism of alpha(v)beta(6) is emerging as a potential treatment of idiopathic pulmonary fibrosis based on strong target validation. Starting from an alpha(v)beta(3) antagonist lead and through simple variation in the nature and position of the aryl substituent, the discovery of compounds with improved alpha(v)beta(6) activity is described. The compounds also have physicochemical properties commensurate with oral bioavailability and are high quality starting points for a drug discovery program. Compounds 33S and 43E1 are pan av antagonists having ca. 100 nM potency against alpha(v)beta(3), alpha(v)beta(5), alpha(v)beta(6), and av beta 8 in cell adhesion assays. Detailed structure activity relationships with these integrins are described which also reveal substituents providing partial selectivity (defined as at least a 0.7 log difference in pIC(50) values between the integrins in question) for alpha(v)beta(3) and alpha(v)beta(5).

  DOI：

  10.1021/ml5002079
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 盐酸 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 ethyl (+/-)-3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride
  参考文献：
  名称：

  Aromatic β-Amino Acids as Asp-Phg Mimics in LDV Derived VLA-4 Antagonists­

  摘要：

  芳香性 β-氨基酸酯 2a-h 通过 Radionow 反应或基于 Davis 描述的方法制备成外消旋形式和手性纯形式，并作为模拟 LDV 衍生的 VLA-4 拮抗剂中的 Asp-Phg C 末端。作为一种有前景的 β-氨基酸酯，11 被鉴定并用以合成高效力的 VLA-4 拮抗剂 S9059，其在细胞粘附试验中的 IC50 值为 1.6 nM。

  DOI：

  10.1055/s-2002-34389

文献信息

• Aromatic β-Amino Acids as Asp-Phg Mimics in LDV Derived VLA-4 Antagonists­
  作者：Volkmar Wehner、Horst Blum、Michael Kurz、Hans Stilz

  DOI：10.1055/s-2002-34389

  日期：——

  Aromatic β-amino acid esters 2a-h were prepared in racemic and enantiomerically pure form by the Radionow reaction or based on the method described by Davis and used as mimics of the Asp-Phg C-terminus in LDV derived VLA-4 antagonists. As a promising β-amino acid ester, 11 was identified and used for the synthesis of the highly potent VLA-4 antagonist S9059 with an IC50 of 1.6 nM in a cell attachment assay.

  芳香性 β-氨基酸酯 2a-h 通过 Radionow 反应或基于 Davis 描述的方法制备成外消旋形式和手性纯形式，并作为模拟 LDV 衍生的 VLA-4 拮抗剂中的 Asp-Phg C 末端。作为一种有前景的 β-氨基酸酯，11 被鉴定并用以合成高效力的 VLA-4 拮抗剂 S9059，其在细胞粘附试验中的 IC50 值为 1.6 nM。
• An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers
  作者：Gábor Tasnádi、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2008.08.009

  日期：2008.9

  An efficient synthesis of β-aryl-β-amino acid enantiomers has been developed via the lipase-catalysed enantioselective hydrolysis of the corresponding racemic ethyl esters in an organic solvent. High enantioselectivities (E >100) were observed when the lipase PS-catalysed reactions were performed with H2O (0.5 equiv) in diisopropyl ether at 45 °C. The products could be easily separated and were obtained

  通过在有机溶剂中通过脂肪酶催化的相应外消旋乙酯的对映选择性水解，已经开发了β-芳基-β-氨基酸对映体的有效合成。当脂肪酶PS催化的H 2 O（0.5当量）在二异丙醚中于45°C进行时，观察到高对映选择性（E > 100）。产物易于分离，收率⩾40％。
• Beta-amino acid derivatives as integrin receptor antagonists
  申请人：——

  公开号：US20040058904A1

  公开（公告）日：2004-03-25

  The present invention relates to compounds of the general formula (I), processes for their preparation, pharmaceutical compositions containing them as well as their use for the production of pharmaceutical compositions for the treatment of inflammatory diseases.

  本发明涉及一般式（I）的化合物，其制备过程，包含它们的制药组合物以及它们用于制备治疗炎症性疾病的制药组合物。
• BETA-AMINO ACID DERIVATIVES AS INTEGRIN RECEPTOR ANTAGONISTS
  申请人：Bayer Aktiengesellschaft

  公开号：EP1326828A1

  公开（公告）日：2003-07-16
• US6333338B1
  申请人：——

  公开号：US6333338B1

  公开（公告）日：2001-12-25