(S)-N-butyl-6-methoxy-(α-methyl)-2-naphthalenacetamide | 139092-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N-butyl-6-methoxy-(α-methyl)-2-naphthalenacetamide
• 英文别名: (S)-naproxen butyl amide；(2S)-N-butyl-2-(6-methoxynaphthalen-2-yl)propanamide
• CAS: 139092-35-6
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: DGPFMNOIHWUXPW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  萘普生 、 正丁胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(S)-N-butyl-6-methoxy-(α-methyl)-2-naphthalenacetamide
  参考文献：
  名称：

  Stereoselective Interaction of Epimeric Naproxen-RGD Peptides with Human Serum Albumin

  摘要：

  The dependence of the interaction between human serum albumin (HSA) and two epimeric bioconjugates, which contain (S)- or (R)-naproxen (NPX) bound to a cyclopentapeptide with an arginine-glycine-aspartate sequence (cRGD), on the absolute configuration of the naproxen moiety has been studied using several complementary experiments, such as direct physical separation of the unbound compound, fluorescence quenching of the protein, circular dichroism, and laser flash photolysis. The results were compared with those obtained with model compounds, such as (S)- and (R)-NPX, cRGD, and (S)- and (R)-NPX-NHBu amide analogues. Fluorescence quenching of Trp-214 in HSA by the naproxen compounds (NPXs) revealed lower efficiency for (S)-NPX-RGD in quenching the Trp emission as compared to (R)-NPX-cRGD. Laser flash photolysis data together with the association constants gave information about the distribution of each compound in site I and II, as well as about the lifetime of their triplet excited state within each site of HSA. Furthermore, docking modeling agreed with different modes of binding of the epimeric bioconjugates. Thus, although both bioconjugates bound preferentially to site I, only the NPX moiety of (R)-NPX-cRGD was located within the cavity, explaining its efficiency for Trp-214 fluorescence quenching.

  DOI：

  10.1021/bm100808d

文献信息

• Cyclic Guanidine Organic Catalysts: What Is Magic About Triazabicyclodecene?
  作者：Matthew K. Kiesewetter、Marc D. Scholten、Nicole Kirn、Ryan L. Weber、James L. Hedrick、Robert M. Waymouth

  DOI：10.1021/jo902369g

  日期：2009.12.18

  The bicyclic guanidine 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (TBO) reveal it to be a much less active acylation catalyst than TBD. Theoretical and mechanistic Studies imply that the higher reactivity of TBD is a consequence of both its higher basicity and nucleophilicity than TBO as well as the high reactivity of the acyl-TBD intermediate, which is sterically prevented from adopting a planar amide structure.
• Stereoselective Interaction of Epimeric Naproxen-RGD Peptides with Human Serum Albumin
  作者：María González-Béjar、Emilio Alarcón、Horacio Poblete、Juan C. Scaiano、Julia Pérez-Prieto

  DOI：10.1021/bm100808d

  日期：2010.9.13

  The dependence of the interaction between human serum albumin (HSA) and two epimeric bioconjugates, which contain (S)- or (R)-naproxen (NPX) bound to a cyclopentapeptide with an arginine-glycine-aspartate sequence (cRGD), on the absolute configuration of the naproxen moiety has been studied using several complementary experiments, such as direct physical separation of the unbound compound, fluorescence quenching of the protein, circular dichroism, and laser flash photolysis. The results were compared with those obtained with model compounds, such as (S)- and (R)-NPX, cRGD, and (S)- and (R)-NPX-NHBu amide analogues. Fluorescence quenching of Trp-214 in HSA by the naproxen compounds (NPXs) revealed lower efficiency for (S)-NPX-RGD in quenching the Trp emission as compared to (R)-NPX-cRGD. Laser flash photolysis data together with the association constants gave information about the distribution of each compound in site I and II, as well as about the lifetime of their triplet excited state within each site of HSA. Furthermore, docking modeling agreed with different modes of binding of the epimeric bioconjugates. Thus, although both bioconjugates bound preferentially to site I, only the NPX moiety of (R)-NPX-cRGD was located within the cavity, explaining its efficiency for Trp-214 fluorescence quenching.