N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-3-(3-hydroxyphenyl)-3-oxopropan-1-amine hydrochloride

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-3-(3-hydroxyphenyl)-3-oxopropan-1-amine hydrochloride
• 英文别名: 1-(3-hydroxyphenyl)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]propan-1-one;hydrochloride
• 化学式: C₁₈H₂₁NO₃*ClH
• 分子量: 335.831
• InChiKey: MXNODEWVNSVLPG-QRGZVCNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  69.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 3-羟基苯乙酮 、 DL-苯丙醇胺盐酸盐 在 三氟化硼乙醚 作用下， 以 异丙醇 为溶剂， 以90%的产率得到N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-3-(3-hydroxyphenyl)-3-oxopropan-1-amine hydrochloride
  参考文献：
  名称：

  Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking

  摘要：

  Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90 kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90 kcal/mol, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.096

文献信息

• Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking
  作者：K. Chennakesava Rao、K. Easwaramoorthi、Y. Arun、C. Balachandran、K.S. Muralidhara Rao、M. Govindhan、Nobuhiko Emi、T. Prakasam、P.T. Perumal

  DOI：10.1016/j.bmcl.2015.07.096

  日期：2015.10

  Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90 kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90 kcal/mol, respectively. (C) 2015 Elsevier Ltd. All rights reserved.