methyl 2-acetamido-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate | 1353674-02-8

• 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: methyl 2-acetamido-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate
• 英文别名: methyl 2-acetamido-3-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]propanoate
• CAS: 1353674-02-8
• 化学式: C₂₀H₂₇BN₂O₅
• 分子量: 386.256
• InChiKey: DQOZIEQYGVJOIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到2-acetamido-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Direct, Regioselective, and Chemoselective Preparation of Novel Boronated Tryptophans by Friedel–Crafts Alkylation

  摘要：

  A facile synthetic approach to the direct preparation of various novel unnatural boronated protected tryptophans using a regio- and chemoselective electrophilic substitution of 4- and 5-boronated indoles with N-protected dehydroalanine is described. The gram-scale synthesis of two free tryptophan boronic acids is also reported.

  DOI：

  10.1021/ol203216h
• 作为产物：
  描述：

  联硼酸频那醇酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium acetate 、 二氯乙基铝 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl 2-acetamido-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Direct, Regioselective, and Chemoselective Preparation of Novel Boronated Tryptophans by Friedel–Crafts Alkylation

  摘要：

  A facile synthetic approach to the direct preparation of various novel unnatural boronated protected tryptophans using a regio- and chemoselective electrophilic substitution of 4- and 5-boronated indoles with N-protected dehydroalanine is described. The gram-scale synthesis of two free tryptophan boronic acids is also reported.

  DOI：

  10.1021/ol203216h

文献信息

• Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy
  作者：Chun-Ming Chio、Ying-Cheng Huang、You-Cheng Chou、Fu-Chun Hsu、Yen-Buo Lai、Chung-Shan Yu

  DOI：10.1021/acsmedchemlett.0c00064

  日期：2020.4.9

  Boron neutron capture therapy (BNCT) is a binary therapeutic approach. Nonradioactive boron-10 atoms accumulated in tumor cells combining with the neutron beams produce two highly energetic particles that could eradicate the cell that takes it and the neighboring cells. Small molecules that carry boron atom, e.g. 5- and 6-boronated and 2,7-diboronated tryptophans, were assessed for their boron accumulation in U87-MG, LN229, and 3T3 for BNCT. TriBoc tryptophan, TB-6-BT, shows boron-10 at 300 ppm in both types of tumor cells with a tumor to normal ratio (T/N) of 5.19-5.25 (4 h). TB-5-BT and DBA-5-BT show boron-10 at 300 ppm (2 h) in U87-MG cells. TB-5-BT exerts a T/N of >9.66 (1 h) in LN229 compared with the current clinical boronophenyl alanine with a highest T/N of 2.3 (1 h) and accumulation concentration of <50 ppm. TB-5-BT and TB-6-BT warrant further animal study.