3-bromo-N-((2-hydroxy-2-(trifluoromethyl)-2H-chromen-3-yl)methyl)propanamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-bromo-N-((2-hydroxy-2-(trifluoromethyl)-2H-chromen-3-yl)methyl)propanamide
• 英文别名: 3-bromo-N-[[2-hydroxy-2-(trifluoromethyl)chromen-3-yl]methyl]propanamide
• 化学式: C₁₄H₁₃BrF₃NO₃
• 分子量: 380.161
• InChiKey: ZIVYTQLEHURVJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 在 sodium tetrahydroborate 、 tetrafluoroboric acid diethyl ether complex 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 3-bromo-N-((2-hydroxy-2-(trifluoromethyl)-2H-chromen-3-yl)methyl)propanamide
  参考文献：
  名称：

  Synthesis of novel amide functionalized 2H-chromene derivatives by Ritter amidation of primary alcohol using HBF4·OEt2 as a mild and versatile reagent and evaluation of their antimicrobial and anti-biofilm activities

  摘要：

  A series of novel amide functionalized 2H-chromene derivatives 3 were prepared starting from ethyl-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 1 via sodium borohydride reduction followed by Ritter amidation using HBF4 center dot OEt2 as a mild and versatile reagent. All the products 3 were screened for antimicrobial activity against various Gram-positive, Gram-negative bacteria and fungal strain. The promising derivatives such as 3f, 3g, 3k, 3l, 3m, 3n and 3o were further screened for minimum bactericidal concentration and bio-film inhibition activity and identified the potential ones. Among all the promising, compound 3g was more potent for antimicrobial, MBC and anti bio-film activities. The structure verses activity relationship of 3g revealed that the presence of two bromine atoms at sixth and R position promotes high activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.041

文献信息

• Synthesis of novel amide functionalized 2H-chromene derivatives by Ritter amidation of primary alcohol using HBF4·OEt2 as a mild and versatile reagent and evaluation of their antimicrobial and anti-biofilm activities
  作者：K. Ratnakar Reddy、Y. Poornachandra、G. Jitender Dev、G. Mallareddy、Jagadeesh B. Nanubolu、C. Ganesh Kumar、B. Narsaiah

  DOI：10.1016/j.bmcl.2015.05.041

  日期：2015.8

  A series of novel amide functionalized 2H-chromene derivatives 3 were prepared starting from ethyl-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 1 via sodium borohydride reduction followed by Ritter amidation using HBF4 center dot OEt2 as a mild and versatile reagent. All the products 3 were screened for antimicrobial activity against various Gram-positive, Gram-negative bacteria and fungal strain. The promising derivatives such as 3f, 3g, 3k, 3l, 3m, 3n and 3o were further screened for minimum bactericidal concentration and bio-film inhibition activity and identified the potential ones. Among all the promising, compound 3g was more potent for antimicrobial, MBC and anti bio-film activities. The structure verses activity relationship of 3g revealed that the presence of two bromine atoms at sixth and R position promotes high activity. (C) 2015 Elsevier Ltd. All rights reserved.