trans-N-phenyl-3-ethoxycarbonyl-4-(2-furyl)-2-azetidinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: trans-N-phenyl-3-ethoxycarbonyl-4-(2-furyl)-2-azetidinone
• 英文别名: ethyl (2S,3R)-2-(furan-2-yl)-4-oxo-1-phenylazetidine-3-carboxylate
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: MWKJRRWGCVFGMG-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-N-phenyl-3-ethoxycarbonyl-4-(2-furyl)-2-azetidinone 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以68%的产率得到trans-N-phenyl-4-(2-furyl)-2-azetidinone-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and characterization of dual inhibitors against new targets FabG4 and HtdX of Mycobacterium tuberculosis

  摘要：

  Herein, we present dual inhibitors of new targets FabG4 and HtdX for the first time. In this work, eight compounds have been designed, synthesized, characterized and evaluated for bio-activities. Amongst them, six compounds have shown inhibitory activities. Three of them (12-14) demonstrate dual inhibition of both FabG4 and HtdX at low micromolar concentration. In addition, the dual inhibitors show good anti-mycobacterial properties against both planktonic growth and biofilm culture of Mycobacterium species. This study is an important addition to tuberculosis drug discovery because it explores two new enzymes as drug targets and presents their dual inhibitors as good candidates for pre-clinical trials. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.007
• 作为产物：
  描述：

  苯基羟胺 在 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 trans-N-phenyl-3-ethoxycarbonyl-4-(2-furyl)-2-azetidinone
  参考文献：
  名称：

  Design, synthesis and characterization of dual inhibitors against new targets FabG4 and HtdX of Mycobacterium tuberculosis

  摘要：

  Herein, we present dual inhibitors of new targets FabG4 and HtdX for the first time. In this work, eight compounds have been designed, synthesized, characterized and evaluated for bio-activities. Amongst them, six compounds have shown inhibitory activities. Three of them (12-14) demonstrate dual inhibition of both FabG4 and HtdX at low micromolar concentration. In addition, the dual inhibitors show good anti-mycobacterial properties against both planktonic growth and biofilm culture of Mycobacterium species. This study is an important addition to tuberculosis drug discovery because it explores two new enzymes as drug targets and presents their dual inhibitors as good candidates for pre-clinical trials. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.007

文献信息

• Differential effects of stereochemistry and C-4 substituents on the enantioselectivity of PLE and PPL catalyzed hydrolysis of 3,4-disubstituted β-lactams
  作者：Amit Basak、Tapan Mahato、Gautam Bhattacharya、Ballari Mukherjee

  DOI：10.1016/s0040-4039(96)02381-7

  日期：1997.1

  Pig Liver Esterase (PLE) and Pig Pancreas Lipase (PPL) catalysed hydrolysis of (+/-)trans-3-carbethoxy and (+/-) cis-3-acetoxymethyl 4-substituted beta-lactams revealed interesting dependence on C-3, C-4 stereochemistry and nature of C-4 substituents. (C) 1997, Elsevier Science Ltd. All rights reserved.