2-氨基-4-(2-氯苯基)丁酸 | 1251999-74-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 2-氨基-4-(2-氯苯基)丁酸
• 英文名称: 2-amino-4-(2-chlorophenyl)butanoic acid
• CAS: 1251999-74-2
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: ZYQDUOLAVXZHAL-UHFFFAOYSA-N

物化性质

• 沸点：
  355.6±37.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  2-氨基-4-(2-氯苯基)丁酸 、 二碳酸二叔丁酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以2.25 g的产率得到2-tert-butoxycarbonylamino-4-(2-chlorophenyl)butyric acid
  参考文献：
  名称：

  Facile Synthesis of ortho-Halo-Substituted 4-Aryl-2-Aminobutyric Acids

  摘要：

  在此，我们介绍了一种高效实用的 4-(5-溴/氯吡唑-1-基)-2-氨基丁酸的区域选择性合成路线。这些化合物是通过 1-(3,3-二甲氧基丙基)-1H-吡唑的区域选择性 C-5 卤化反应，然后用 Strecker 合成法制备的。此外，还合成了受 Boc 保护的 2-氨基-4-(2-氯苯基)丁酸和 2-氨基-4-(3-氯吡啶-2-基)丁酸。

  DOI：

  10.1055/s-2008-1032194
• 作为产物：
  描述：

  2-Amino-4-(2-chlorophenyl)butanenitrile 在 盐酸 作用下， 反应 8.0h， 生成 2-氨基-4-(2-氯苯基)丁酸
  参考文献：
  名称：

  Facile Synthesis of ortho-Halo-Substituted 4-Aryl-2-Aminobutyric Acids

  摘要：

  在此，我们介绍了一种高效实用的 4-(5-溴/氯吡唑-1-基)-2-氨基丁酸的区域选择性合成路线。这些化合物是通过 1-(3,3-二甲氧基丙基)-1H-吡唑的区域选择性 C-5 卤化反应，然后用 Strecker 合成法制备的。此外，还合成了受 Boc 保护的 2-氨基-4-(2-氯苯基)丁酸和 2-氨基-4-(3-氯吡啶-2-基)丁酸。

  DOI：

  10.1055/s-2008-1032194

文献信息

• Changing the selectivity profile – from substrate analog inhibitors of thrombin and factor Xa to potent matriptase inhibitors
  作者：Alexander Maiwald、Maya Hammami、Sebastian Wagner、Andreas Heine、Gerhard Klebe、Torsten Steinmetzer

  DOI：10.3109/14756366.2016.1172574

  日期：2016.11.1

  trypsin, the obtained complex was used to model the binding mode of inhibitor 35 in the active site of matriptase. The methylene insertion in d-hTyr and d-hPhe increases the flexibility of the P3 side chain compared to their d-Phe analogs, which enables an improved binding of these inhibitors in the well-defined S3/4 pocket of matriptase. Inhibitor 35 can be used for further biochemical studies with

  II型跨膜丝氨酸蛋白酶麦芽糖酶是抗癌治疗的潜在靶标，可能与骨关节炎或炎性皮肤疾病中的软骨降解有关。从先前描述的非特异性凝血酶和Xa因子抑制剂开始，我们已经制备了新的非共价底物类似物，其对麦芽糖酶的功效更高。最合适的化合物35（Hd-hTyr-Ala-4- d基苄基酰胺）以26 nM的抑制常数与麦芽糖酶结合，并且对凝血酶和Xa因子的活性降低了10倍以上。在替代蛋白酶胰蛋白酶中测定抑制剂35的晶体结构，将所获得的复合物用于模拟在苹果酸酶的活性位点中抑制剂35的结合模式。与它们的d-Phe类似物相比，在d-hTyr和d-hPhe中的亚甲基插入增加了P3侧链的柔韧性，这使得这些抑制剂能够更好地结合在苹果酸酶的明确定义的S3 / 4口袋中。抑制剂35可与脂蛋白酶一起用于进一步的生化研究。
• 1,4-BENZODIAZEPINONE COMPOUNDS AND THEIR USE IN TREATING CANCER
  申请人：Glick Gary D.

  公开号：US20120094982A1

  公开（公告）日：2012-04-19

  The invention provides a family of 1,4-benzodiazepinone compounds and methods for their use as therapeutic agents in treating cancer. Pharmaceutical compositions and methods of making the 1,4-benzodiazepinone compounds are provided.

  该发明提供了一系列1,4-苯二氮卓酮化合物及其在治疗癌症中作为治疗剂的使用方法。还提供了制备1,4-苯二氮卓酮化合物的药物组合物和方法。
• METHOD FOR PREPARING AROMATIC AMINO ACID DERIVATIVE
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20220144762A1

  公开（公告）日：2022-05-12

  The present invention provides methods of efficiently producing various optically active aromatic amino acid derivatives by reacting, using an additive, a specific ester compound with an aromatic halide and zinc in the presence of a catalyst. The present invention also provides amino acid derivatives that can be produced by the methods.

  本发明提供了一种通过在催化剂存在下，使用添加剂，将特定酯化合物与芳香卤化物和锌反应的方法，有效地生产各种光学活性芳香族氨基酸衍生物。本发明还提供了可以通过这些方法生产的氨基酸衍生物。
• CYCLIC PEPTIDE COMPOUND HAVING HIGH MEMBRANE PERMEABILITY, AND LIBRARY CONTAINING SAME
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP3636807A1

  公开（公告）日：2020-04-15

  The present inventors have found that when screening for cyclic peptide compounds that can specifically bind to a target molecule, the use of a library including cyclic peptide compounds having a long side chain in the cyclic portion can improve the hit rate for cyclic peptide compounds that can specifically bind to the target molecule. Meanwhile, the present inventors have found that tryptophan and tyrosine residues, which have conventionally been used in oral low molecular-weight pharmaceuticals and are amino acid residues having an indole skeleton or a hydroxyphenyl group, are not suitable for peptides intended to attain high membrane permeability.

  本发明人发现，在筛选能与目标分子特异性结合的环肽化合物时，使用包括环状部分具有长侧链的环肽化合物库，可以提高能与目标分子特异性结合的环肽化合物的命中率。同时，本发明者发现色氨酸和酪氨酸残基不适合用于旨在获得高膜渗透性的肽，这两种残基通常用于口服低分子量药物，是具有吲哚骨架或羟基苯基的氨基酸残基。
• METHOD FOR PRODUCING CYCLIC ORGANIC COMPOUND
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20210147475A1

  公开（公告）日：2021-05-20

  An objective of the present invention is to provide methods of producing a cyclic organic compound using a continuous stirred tank reactor(s) (CSTR), the methods being capable of achieving excellent impurity-suppressing effects (quality improvement), reduction in reaction-tank size, continuous production, and such. The present inventors conducted studies on cyclization reactions using a CSTR(s), which had not been conventionally used for cyclization reactions for cyclic compounds. As a result, the inventors have found that the present methods can achieve excellent impurity-suppressing effects (quality improvement), reduction in reaction-tank size, continuous production, and such, as compared with conventional cyclization methods. Furthermore, the present inventors have also found that the above-mentioned improvement effects can efficiently be achieved even in the production of cyclic peptides and heterocyclic compounds by applying simulation methods that had been conventionally used mainly at the fine chemicals plant level to the cyclization reactions of the present invention, thereby experimentally predicting the reaction rate of a cyclization reaction, and setting the flow volume (residence time), the concentrations of precursor and cyclic organic compound, and the temperature for the cyclization reaction and such which affect these conditions, in the cyclization reaction using a CSTR(s).