2-amino-isobutyric acid tryptamide | 940290-06-2

• 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: 2-amino-isobutyric acid tryptamide
• 英文别名: 2-amino-N-[2-(1H-indol-3-yl)ethyl]-2-methylpropanamide
• CAS: 940290-06-2
• 化学式: C₁₄H₁₉N₃O
• mdl: MFCD11580833
• 分子量: 245.324
• InChiKey: WVRUXKAJDDIWOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 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：

  2-amino-isobutyric acid tryptamide 在 氯甲酸乙酯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 N-(1-(2-(1H-indol-3-yl)ethylamino)-2-methyl-1-oxopropan-2-yl)-3-(4-hydroxyphenyl)acrylamide
  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：

  2-[(benzyloxycarbonyl)amino]-isobutyric acid tryptamide 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 以98%的产率得到2-amino-isobutyric acid 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

• Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
  作者：Päivi H. Kiviranta、Heikki S. Salo、Jukka Leppänen、Valtteri M. Rinne、Sergiy Kyrylenko、Erkki Kuusisto、Tiina Suuronen、Antero Salminen、Antti Poso、Maija Lahtela-Kakkonen、Erik A.A. Wallén

  DOI：10.1016/j.bmc.2008.07.059

  日期：2008.9

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.
• N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors
  作者：Päivi H. Kiviranta、Jukka Leppänen、Valtteri M. Rinne、Tiina Suuronen、Olga Kyrylenko、Sergiy Kyrylenko、Erkki Kuusisto、Anu J. Tervo、Tomi Järvinen、Antero Salminen、Antti Poso、Erik A.A. Wallén

  DOI：10.1016/j.bmcl.2007.02.023

  日期：2007.5

  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.