5-bromo-N_α-acetyltryptophan methyl ester | 114872-69-4

• 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: 5-bromo-N_α-acetyltryptophan methyl ester
• 英文别名: 5-bromo-(N-acetyl)tryptophan methyl ester；methyl 2-acetamido-3-(5-bromo-1H-indol-3-yl)propanoate
• CAS: 114872-69-4
• 化学式: C₁₄H₁₅BrN₂O₃
• 分子量: 339.189
• InChiKey: BMKLAXMLZFZQET-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  555.3±50.0 °C(predicted)
• 密度：
  1.496±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-N_α-acetyltryptophan methyl ester 在 劳森试剂 、 碘甲烷 作用下， 以 乙二醇二甲醚 、 丙酮 为溶剂， 反应 10.0h， 生成 6-bromo-3-(methoxycarbonyl)-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-2-ium iodide
  参考文献：
  名称：

  通过2-硝基苯并呋喃的脱芳香族[3 + 2]环加成反应对映选择性地合成多环环丙烷。

  摘要：

  通过2-硝基苯并呋喃与环甲亚胺基团的不对称脱芳环加成反应，成功开发了直接合成熔融多环托烷骨架的方法。在衍生自Cu（OAc）2和二膦配体的手性铜配合物的存在下，以高收率（75-91％）和优异的对映选择性（90-98％）获得了一系列稠合的多环环烷衍生物。产品的便捷转换展示了这种方法的实用性。

  DOI：

  10.1021/acs.orglett.9b04108
• 作为产物：
  描述：

  5-溴吲哚 在 乙酸酐 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 4.0h， 生成 5-bromo-N_α-acetyltryptophan methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.028

文献信息

• Switchable Reactivity of Acylated α, β-Dehydroamino Ester in the Friedel−Crafts Alkylation of Indoles by Changing the Lewis Acid
  作者：Elena Angelini、Cesarino Balsamini、Francesca Bartoccini、Simone Lucarini、Giovanni Piersanti

  DOI：10.1021/jo800881u

  日期：2008.7.1

  Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.
• 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.
• PORTER, JOHN;DYKERT, JOHN;RIVIER, JEAN, INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 1, 13-21
  作者：PORTER, JOHN、DYKERT, JOHN、RIVIER, JEAN

  DOI：——

  日期：——