3-(2-Phenylethylamino)propane-1,2-diol | 109208-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-Phenylethylamino)propane-1,2-diol
• CAS: 109208-45-9
• 化学式: C₁₁H₁₇NO₂
• mdl: MFCD16471987
• 分子量: 195.261
• InChiKey: PPIJUEGSCFWSQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-Phenylethylamino)propane-1,2-diol 在 吡啶 、 盐酸 、 sodium acetate 、 sodium hydride 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 27.5h， 生成 1-Phenethylamino-3-[4-(5-thiophen-2-yl-1H-imidazol-2-yl)-phenoxy]-propan-2-ol
  参考文献：
  名称：

  .beta.1-Selective adrenoceptor antagonists: examples of the 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazole class

  摘要：

  A series of 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazoles is described. The compounds were investigated in vitro for beta-adrenoceptor antagonism, and several examples were found to be selective for the beta 1-adrenoceptor. The structure--activity relationship exhibited by this series of compounds is discussed. (S)-2-[p-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-2-hydroxypropoxy]phenyl]-4-(2 -thienyl)imidazole [(S)-13] was over 100 times more selective than atenolol for the beta 1-adrenergic receptor and has been selected for in-depth studies.

  DOI：

  10.1021/jm00361a004
• 作为产物：
  描述：

  缩水甘油 、 2-苯乙胺 以 异丙醇 为溶剂， 生成 3-(2-Phenylethylamino)propane-1,2-diol
  参考文献：
  名称：

  .beta.1-Selective adrenoceptor antagonists: examples of the 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazole class

  摘要：

  A series of 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazoles is described. The compounds were investigated in vitro for beta-adrenoceptor antagonism, and several examples were found to be selective for the beta 1-adrenoceptor. The structure--activity relationship exhibited by this series of compounds is discussed. (S)-2-[p-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-2-hydroxypropoxy]phenyl]-4-(2 -thienyl)imidazole [(S)-13] was over 100 times more selective than atenolol for the beta 1-adrenergic receptor and has been selected for in-depth studies.

  DOI：

  10.1021/jm00361a004

文献信息

• Enhanced cellular uptake by “pharmaceutically oriented devices” of new simplified analogs of Linezolid with antimicrobial activity
  作者：Ortensia Ilaria Parisi、Marco Fiorillo、Anna Caruso、Anna Rita Cappello、Carmela Saturnino、Francesco Puoci、Antonella Panno、Vincenza Dolce、Hussein El-Kashef、Maria Stefania Sinicropi

  DOI：10.1016/j.ijpharm.2013.11.048

  日期：2014.1

  The aim of the present study was to enhance cellular uptake of simplified analogs of Linezolid by their incorporation into suitable delivery devices in order to improve the antimicrobial activity of these novel synthesized oxazolidin-2-one derivatives. The oxazolidin-2-one derivatives were synthesized by developing a rather simple one-pot reaction starting from oxiranylmethanol and several primary amines. Three delivery devices were prepared by following different synthetic approaches, such as single-step free radical grafting, precipitation polymerization and nano-emulsion. Finally, the antimicrobial activity of the novel synthesized compounds, without any vehicle and after their incorporation into the delivery devices, was evaluated against Escherichia coli and Saccharomyces cerevisiae by performing time-kill analyses. The synthesized oxazolidinones exhibited modest antimicrobial activity against E. coli and S. cerevisiae (MIC 16 vg/mL). A good activity was, instead, highlighted after their incorporation into the prepared delivery devices (lecithin-based nano-emulsion, poly(N-vinyl-pyrrolidone)-methacrylic acid grafted copolymer and spherical polymeric nanoparticles) (MIC < 4 vg/mL). The incorporation into suitable vehicles, indeed, reduced by 4 times the normal MICs of the newly synthesized oxazolilidin-2-ones and represents an effective strategy to overcome cellular penetration constraints. 2013 Elsevier B.V. All rights reserved.
• BALDWIN, J. J.;DENNY, G. H.;HIRSCHMANN, R.;FREEDMAN, M. B.;PONTICELLO, G.+, J. MED. CHEM., 1983, 26, N 7, 950-957
  作者：BALDWIN, J. J.、DENNY, G. H.、HIRSCHMANN, R.、FREEDMAN, M. B.、PONTICELLO, G.+

  DOI：——

  日期：——
• .beta.1-Selective adrenoceptor antagonists: examples of the 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazole class
  作者：John J. Baldwin、George H. Denny、Ralph Hirschmann、Mark B. Freedman、Gerald S. Ponticello、Dennis M. Gross、Charles S. Sweet

  DOI：10.1021/jm00361a004

  日期：1983.7

  A series of 2-[4-[3-(substituted-amino)-2-hydroxypropoxy]phenyl]imidazoles is described. The compounds were investigated in vitro for beta-adrenoceptor antagonism, and several examples were found to be selective for the beta 1-adrenoceptor. The structure--activity relationship exhibited by this series of compounds is discussed. (S)-2-[p-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-2-hydroxypropoxy]phenyl]-4-(2 -thienyl)imidazole [(S)-13] was over 100 times more selective than atenolol for the beta 1-adrenergic receptor and has been selected for in-depth studies.