(S)-3-(4-Methoxy-phenyl)-2-methylamino-propionic acid methyl ester | 162631-41-6

• 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)-3-(4-Methoxy-phenyl)-2-methylamino-propionic acid methyl ester
• 英文别名: methyl (2S)-3-(4-methoxyphenyl)-2-(methylamino)propanoate
• CAS: 162631-41-6
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: GZSRMIFFYCWUHU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Methoxy-phenyl)-2-methylamino-propionic acid methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S)-2-[acetyl(methyl)amino]-3-(4-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  Synthesis of a Reduced Ring Analog of Didemnin B

  摘要：

  As part of investigations directed toward the determination of the essential/nonessential structural features for the bioactivities of didemnin B, we designed a reduced ring analog in which three moieties, namely the tyrosine side chain, the isostatine hydroxyl, and the side chain (L-lactyl-L-prolyl-N-Me-D-leucine), were in their presumed bioactive conformation. In designing the reduced ring analog, we eliminated the leucine-proline portion of the macrocycle core and replaced if with an n-butyl linker in order to elucidate its role. According to MM2 calculations (MacroModel molecular modeling), this analog was of lower energy than the natural product didemnin B, and both structures were superimposable. The synthetic strategy involved four disconnections. Macrocyclization was accomplished at the activated carboxylic acid of the alpha-(alpha-hydroxyisovaleryl)-propionyl unit (HIP) and the protected amine of the n-butyl linker using a modification of Schmidt's protocol. After selective deprotection of the hydroxyl and amino groups of the macrocycle, the peptide side chain was introduced using (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as the activating reagent.

  DOI：

  10.1021/jo9623696
• 作为产物：
  描述：

  methyl (2S)-3-(4-methoxyphenyl)-2-[methyl(phenylmethoxycarbonyl)amino]propanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以91%的产率得到(S)-3-(4-Methoxy-phenyl)-2-methylamino-propionic acid methyl ester
  参考文献：
  名称：

  Didemnin B 的无环类似物的合成

  摘要：

  摘要 报道了环缩肽didemnin B的三个修饰肽片段的合成。didemnin B 大环的 HIP 和异抑制素（第一）单元被简化为 Z-丙氨酸残基，酯键（通过四肽的苏氨酸）通过甘氨酸、D-丙氨酸和乙二胺接头的胺被酰胺键取代. 后者允许连接 N-Me-D-Leu-Pro-Lac 部分以分别提供类似物 2、3 和 4。

  DOI：

  10.1080/00397919708004186

文献信息

• Solution-Phase Parallel Synthesis of a Pharmacophore Library of HUN-7293 Analogues:  A General Chemical Mutagenesis Approach To Defining Structure−Function Properties of Naturally Occurring Cyclic (Depsi)peptides
  作者：Yan Chen、Melitta Bilban、Carolyn A. Foster、Dale L. Boger

  DOI：10.1021/ja020166v

  日期：2002.5.1

  are detailed enlisting solution-phase techniques and simple acid-base liquid-liquid extractions for isolation and purification of intermediates and final products. Significant to the design of the studies and unique to solution-phase techniques, the library was assembled superimposing a divergent synthetic strategy onto a convergent total synthesis. An alanine scan and N-methyl deletion of each residue

  HUN-7293 (1) 是一种天然存在的环状七肽，是细胞粘附分子表达（VCAM-1、ICAM-1、E-选择素）的有效抑制剂，其过度表达是慢性炎症性疾病的特征。定义此类环状 (depsi) 肽的结构-功能关系的一般方法的代表，关键 HUN-7293 类似物的完整库的并行合成和评估是详细的采用液相技术和简单的酸碱液-液提取用于中间体和最终产品的分离和纯化。对于研究的设计和溶液相技术的独特性而言，该库的组装是将发散的合成策略叠加到收敛的全合成上。环七肽每个残基的丙氨酸扫描和 N-甲基缺失确定了负责或促成生物学特性的关键位点。同时制备一套完整的单个残基类似物进一步简化了结构，允许对 1 的每个结构特征进行评估，在单个研究中提供结构-功能关系的详细说明。在通过天然产物结构的系统化学诱变制备的药效团文库中，鉴定了具有可比效力的简化类似物，并且在某些情况下，提高了选择性。该文库的一个有效成员被证明是一种额外的天然产物，我们将其称为
• PSMA-TARGETED NIR DYES AND THEIR USES
  申请人：On Target Laboratories, LLC

  公开号：US20170066719A1

  公开（公告）日：2017-03-09

  The present disclosure relates to prostate specific membrane antigen (PSMA) targeted compounds conjugated to near-infra red (NIR) dyes and methods for their therapeutic and diagnostic use. More specifically, this disclosure provides compounds and methods for diagnosing and treating diseases associated with cells and/or vasculature expressing prostate specific membrane antigen (PSMA), such as prostate cancer and related diseases. The disclosure further describes methods and compositions for making and using the compounds, methods incorporating the compounds, and kits incorporating the compounds.

  本公开涉及针对前列腺特异性膜抗原（PSMA）的靶向化合物，这些化合物与近红外（NIR）染料结合，并且涉及其治疗和诊断用途的方法。更具体地说，本公开提供了用于诊断和治疗与表达前列腺特异性膜抗原（PSMA）的细胞和/或血管相关的疾病，如前列腺癌和相关疾病的化合物和方法。本公开进一步描述了制备和使用这些化合物的方法和组成物，包括将这些化合物纳入方法中和将这些化合物纳入试剂盒中的方法。
• Novel aminomethylene-peptides as immunosuppressants
  申请人：Bayer Corporation

  公开号：EP0610743A1

  公开（公告）日：1994-08-17

  Compounds which suppress human T-lymphocyte proliferation are disclosed. The active compounds essentially contain at least the following structure:

  本发明公开了抑制人类 T 淋巴细胞增殖的化合物。活性化合物基本上至少包含以下结构：
• Aminomethylene-peptides as immunosuppressants
  申请人：Bayer Corporation

  公开号：EP0610743B1

  公开（公告）日：1998-09-09
• METHODS OF MANUFACTURE AND SYNTHESIS OF AMINO ACID LINKING GROUPS CONJUGATED TO COMPOUNDS USED FOR TARGETED IMAGING OF TUMORS
  申请人：On Target Laboratories LLC

  公开号：EP2968614B1

  公开（公告）日：2019-04-03