methyl 2-amino-3-(4-nitro-1H-indol-3-yl)propanoate

• 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-amino-3-(4-nitro-1H-indol-3-yl)propanoate
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: PMOBIEZKVZKEGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 DL-色氨酸 在 硝酸 、 溶剂黄146 、 尿素 、 氯化亚砜 作用下， 反应 14.27h， 生成 methyl 2-amino-3-(6-nitro-1H-indol-3-yl)propanoate 、 methyl 2-amino-3-(4-nitro-1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy

  摘要：

  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.

  DOI：

  10.1021/acsmedchemlett.0c00064

文献信息

• [EN] TOTAL SYNTHESIS OF THAXTOMIN A ANALOGUES AND THEIR INTERMEDIATES<br/>[FR] SYNTHÈSE TOTALE D'ANALOGUES DE THAXTOMINE A ET DE LEURS INTERMÉDIAIRES
  申请人：MARRONE BIO INNOVATIONS INC

  公开号：WO2014149171A1

  公开（公告）日：2014-09-25

  Improved synthetic methods for the production of thaxtomin analogues, particularly thaxtomin A, and intermediates therefore such as substituted tryptophans and in particular,4-nitro-L-tryptophan, and substituted phenyl acrylic acids are disclosed. Bioassays show that the synthetic thaxtomin A is not significantly different from the natural one in herbicidal activity.