(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-boronophenyl)propanoic acid | 273221-71-9

• 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: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-boronophenyl)propanoic acid
• 英文别名: Fmoc-4-Borono-L-Phenylalanine；(2S)-3-(4-boronophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 273221-71-9
• 化学式: C₂₄H₂₂BNO₆
• 分子量: 431.253
• InChiKey: KQZPZGIZOXMZJP-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-boronophenyl)propanoic acid 在 N-甲基吗啉 、 hydroxylamine Wang resin 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 哌啶 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 4-((S)-2-(hydroxycarbamoyl)-2-aminoethyl)phenylboronic acid
  参考文献：
  名称：

  Design and Evaluation of Hydroxamate Derivatives as Metal-Mediated Inhibitors of a Protein Tyrosine Kinase

  摘要：

  Protein tyrosine kinases use two Mg2+ ions as cofactors in catalysis, one as the ATP-Mg complex (M1) and the other as an essential activator (M2). The M2-binding site has high affinity for transition metal cations such as cobalt and zinc. Taking advantage of this high affinity, we examined hydroxamates as metal-mediated inhibitors against C-terminal Src kinase (Csk), a protein tyrosine kinase. Of a small group of amino acid hydroxamates, tyrosine and phenylalanine hydroxamates inhibited Csk activity only in the presence of Co2+. Four classes of phenylalanine and tyrosine hydroxamate derivatives were synthesized and evaluated as metal-mediated inhibitors of Csk, leading to improved inhibition and a better understanding of the structure-activity relationships. This study suggests that hydroxamates may serve as a general scaffold for developing metal-mediated inhibitors against protein tyrosine kinases. To the best of our knowledge, this is the first report of designing metal-mediated inhibitors against a protein tyrosine kinase by targeting a metal binding site.

  DOI：

  10.1021/jm061058c
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 potassium acetate 、 palladium diacetate 、 碳酸氢钠 、 三(邻甲基苯基)磷 作用下， 以 2-甲基四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 16.0h， 生成 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-boronophenyl)propanoic acid
  参考文献：
  名称：

  [EN] MACROCYCLIC IMMUNOMODULATORS
  [FR] IMMUNOMODULATEURS MACROCYCLIQUES

  摘要：

  In accordance with the present disclosure, macrocyclic compounds have been discovered that bind to PD-1 and are capable of inhibiting the interaction of PD-1 with PD-L1. These macrocyclic compounds exhibitin vitroimmunomodulatory efficacy thus making them therapeutic candidates for the treatment of various diseases including cancer and infectious diseases.

  公开号：

  WO2023288213A1

文献信息

• [EN] BORYLATED AMINO ACID COMPOSITIONS FOR USE IN BORON NEUTRON CAPTURE THERAPY AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'ACIDES AMINÉS BORYLÉS DESTINÉES À ÊTRE UTILISÉES EN THÉRAPIE PAR CAPTURE DE NEUTRONS PAR LE BORE ET MÉTHODES ASSOCIÉES
  申请人：TAE LIFE SCIENCES

  公开号：WO2020180390A1

  公开（公告）日：2020-09-10

  Borylated Amino Acid ("BAA") compositions and methods of making BAAs are disclosed herein. Consequently, the BAAs can be administered to patients as a Neutron Capture Agent and provide a method of treating cancer, immunological disorders and other disease by utilizing a Neutron Capture Therapy modality.

  本文披露了硼化氨基酸（“BAA”）组合物及制备BAA的方法。因此，可以将BAA用作中子俘获剂向患者施用，并提供了一种利用中子俘获治疗模式治疗癌症、免疫性疾病和其他疾病的方法。
• [EN] MACROCYLIC IMMUNOMODULATORS<br/>[FR] IMMUNOMODULATEURS MACROCYCLIQUES
  申请人：[en]BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO2023004240A1

  公开（公告）日：2023-01-26

  In accordance with the present disclosure, macrocyclic compounds have been discovered that bind to PD-1 and are capable of inhibiting the interaction of PD-1 and PD-L1. These macrocyclic compounds exhibitin vitroimmunomodulatory efficacy thus making them therapeutic candidates for the treatment of various diseases including cancer and infectious diseases.