(S)-2-amino-2-(4-bromophenyl)-propionic acid | 766537-46-6

• 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: (S)-2-amino-2-(4-bromophenyl)-propionic acid
• 英文别名: (S)-(-)-α-4-bromophenylalanine；(S)-2-methyl-2-(p-bromophenyl)glycine；(2S)-2-amino-2-(4-bromophenyl)propanoic acid
• CAS: 766537-46-6
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: LCJMKSWXOYWTFZ-VIFPVBQESA-N

物化性质

• 熔点：
  268 °C
• 沸点：
  363.2±32.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-2-(4-bromophenyl)-propionic acid 在 palladium on activated charcoal 盐酸 、 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
  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-(4-溴苯基)-5-甲基咪唑烷-2,4-二酮 在 盐酸 、 sodium hydroxide 作用下， 生成 (S)-2-amino-2-(4-bromophenyl)-propionic acid
  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

• Efficient Biocatalytic Synthesis of Highly Enantiopureα-Alkylated Arylglycines and Amides
  作者：Mei-Xiang Wang、Shuan-Jun Lin、Jun Liu、Qi-Yu Zheng

  DOI：10.1002/adsc.200303219

  日期：2004.3

  racemic α-alkylarylglycine amides including 1-amino-1-carbamoyl-1,2,3,4-tetrahydronaphthalene underwent efficient biocatalytic hydrolysis under very mild conditions to afford the corresponding (S)-α-alkylarylglycines and (R)-α-alkylarylglycine amides in excellent yields with enantiomeric excesses higher than 99.5%. Both the reaction rate and enantioselectivity of biocatalytic kinetic resolution were strongly

  包括1-氨基-1-氨基甲酰基-1,2,3,4-四氢萘在内的许多外消旋α-烷基芳基甘氨酸酰胺在非常温和的条件下进行了有效的生物催化水解，得到相应的（S）-α-烷基芳基甘氨酸和（R）- α-烷基芳基甘氨酸酰胺具有优异的收率，对映体过量高于99.5％。生物催化动力学拆分的反应速率和对映选择性都强烈取决于取代基的性质和底物苯环上的取代方式。相反，在含腈水化酶/酰胺酶的微生物红球菌的催化下，未观察到源自苯乙酮的Strecker腈的有效生物转化。sp。AJ270全细胞催化剂。结合酰胺的化学水解，该生物转化过程从容易获得的外消旋酰胺提供了两种对映体形式的α-取代的芳基甘氨酸的有效合成。
• Design and scalable synthesis of new chiral selectors. Part 1: Synthesis and characterization of a new constrained cyclopeptide from unnatural bulky amino acids
  作者：Laurent Ferron、Frédéric Guillen、Servane Coste、Gérard Coquerel、Pascal Cardinaël、Joël Schwartz、Jean-Marc Paris、Jean-Christophe Plaquevent

  DOI：10.1016/j.tet.2011.06.032

  日期：2011.8

  We describe the conception, synthesis, and characterization of a novel cyclopeptide designed for chiral recognition. The asymmetric units are built from an unnatural amino acid in the series of α-aryl-α-methyl glycine. Modifications of standard methods of peptide synthesis are described in order to improve yields and purities when applied to hindered amino acids. First set of experiments about host–guest

  我们描述了为手性识别设计的新型环肽的概念，合成和表征。不对称单元由一系列α-芳基-α-甲基甘氨酸中的非天然氨基酸构成。描述了对肽合成的标准方法的修改，以便在应用于受阻氨基酸时提高产量和纯度。公开了关于获得的环肽的宿主-客体能力的第一组实验。
• Enantioselective and diastereoselective synthesis of fluorinated dipeptides by late electrophilic fluorination
  作者：Barbara Mohar、Damjan Sterk、Laurent Ferron、Dominique Cahard

  DOI：10.1016/j.tetlet.2005.05.074

  日期：2005.7

  A series of optically enriched monofluorinated dipeptides incorporating an α-fluoro-α-amino acid were prepared by enantio- and diastereoselective electrophilic fluorination. This previously unsuccessful approach to fluorinated dipeptides can now be achieved with up to 73:27 enantiomeric ratio and high >98:2 diastereomeric ratio.

  通过对映和非对映选择性亲电氟化制备了一系列掺有α-氟-α-氨基酸的光学富集的单氟化二肽。现在可以以高达73:27的对映体比例和高的> 98：2非对映体比例来实现这种以前不成功的氟化二肽方法。
• Imidazolidine derivatives, their preparation, their use, and pharmaceutical preparations comprising them
  申请人：——

  公开号：US20030125565A1

  公开（公告）日：2003-07-03

  The present invention relates to novel imidazolidine derivatives of the formula I, 1 in which B, E, W, Z, R, R 0 , R 2 , R 3 , e and h have the meanings indicated in the application. The compounds of the formula I are valuable pharmaceutical active compounds, which are suitable, for example, for the therapy and prophylaxis of inflammatory disorders, for example of rheumatoid arthritis, or of allergic disorders. The compounds of the formula I are inhibitors of the adhesion and migration of leucocytes and/or antagonists of the adhesion receptor VLA-4 belonging to the integrins group. They are generally suitable for the therapy or prophylaxis of illnesses which are caused by an undesired extent of leucocyte adhesion and/or leucocyte migration or are associated therewith, or in which cell-cell or cell-matrix interactions which are based on interactions of VLA-4 receptors with their ligands play a part. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use in the therapy and prophylaxis of the disease states mentioned and pharmaceutical preparations which contain compounds of the formula I.

  本发明涉及公式I的新型咪唑啉衍生物，其中B、E、W、Z、R、R0、R2、R3、e和h在申请书中所示。公式I的化合物是有价值的药物活性化合物，适用于治疗和预防炎症性疾病，例如类风湿性关节炎或过敏性疾病。公式I的化合物是白细胞粘附和迁移的抑制剂和/或属于整合素组的粘附受体VLA-4的拮抗剂。它们通常适用于由白细胞粘附和/或白细胞迁移的不良程度引起或与之相关的疾病的治疗或预防，或者在其中基于VLA-4受体与其配体的相互作用的细胞-细胞或细胞-基质相互作用发挥作用。此外，本发明还涉及公式I化合物的制备方法，它们在上述疾病状态的治疗和预防中的应用以及含有公式I化合物的制药制剂。
• (4-hydroxypyrrolidin-2-yl)-heterocyclic compounds and methods of use thereof
  申请人：Genentech, Inc.

  公开号：US11242344B2

  公开（公告）日：2022-02-08

  The present disclosure relates to bifunctional compounds, which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands.

  本公开涉及可用作靶向泛素化调节剂的双功能化合物。特别是，本公开涉及的化合物一端含有与 VHL E3 泛素连接酶结合的 VHL 配体分子，另一端含有与靶蛋白结合的分子，从而实现靶蛋白/多肽的降解。还公开了 VHL 配体。