D-alanine tryptamide | 940290-21-1

• 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: D-alanine tryptamide
• 英文别名: (2R)-2-amino-N-[2-(1H-indol-3-yl)ethyl]propanamide
• CAS: 940290-21-1
• 化学式: C₁₃H₁₇N₃O
• mdl: MFCD16260579
• 分子量: 231.297
• InChiKey: BXRMLVCQKPUWLI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-alanine tryptamide 在 sodium methylate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.25h， 生成 (2R)-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]-N-[2-(1H-indol-3-yl)ethyl]propanamide
  参考文献：
  名称：

  N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors

  摘要：

  A series of N-(3-(4-hydroxyphenyl)-propenoyl)-amino acid tryptamides was based on a previously reported new SIRT2 inhibitor from our group, and it was designed to study if the molecular size of the compound could be reduced. The most potent compounds, N-(3-(4-hydroxyphenyl)-propenoyl)-2-aminoisobutyric acid tryptamide and N-(3-(4-hydroxyphenyl)-propenoyl)-L-alanine tryptamide, were equipotent, 30% smaller in molecular weight, and slightly more selective (SIRT2/SIRT1) than the parent compound. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.023
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-D-alanine tryptamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到D-alanine tryptamide
  参考文献：
  名称：

  N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors

  摘要：

  A series of N-(3-(4-hydroxyphenyl)-propenoyl)-amino acid tryptamides was based on a previously reported new SIRT2 inhibitor from our group, and it was designed to study if the molecular size of the compound could be reduced. The most potent compounds, N-(3-(4-hydroxyphenyl)-propenoyl)-2-aminoisobutyric acid tryptamide and N-(3-(4-hydroxyphenyl)-propenoyl)-L-alanine tryptamide, were equipotent, 30% smaller in molecular weight, and slightly more selective (SIRT2/SIRT1) than the parent compound. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.023

文献信息

• Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
  作者：Marco T. Sabatini、Valerija Karaluka、Rachel M. Lanigan、Lee T. Boulton、Matthew Badland、Tom D. Sheppard

  DOI：10.1002/chem.201800372

  日期：2018.5.11

  Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also

  已使用多种“经典”偶联剂，化学计量或催化基团（IV）金属盐和硼路易斯酸研究了未保护氨基酸的酰胺化。通过尝试合成衍生自二十种天然和几种非天然氨基酸以及广泛选择的伯胺和仲胺的酰胺，探索了反应的范围。该研究还研究了药用相关化合物的合成，以及这种直接酰胺化方法的可扩展性。最后，我们提供了对在这些反应中观察到的化学选择性的见解。