(S)-2-(4-methylene-5-oxotetrahydrofuran-3-yl)ethyl (4-methoxyphenyl)carbamate

• 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: (S)-2-(4-methylene-5-oxotetrahydrofuran-3-yl)ethyl (4-methoxyphenyl)carbamate
• 英文别名: 2-[(3S)-4-methylidene-5-oxooxolan-3-yl]ethyl N-(4-methoxyphenyl)carbamate
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: RQJMIGWOOUHUGV-LLVKDONJSA-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  cis-4-hydroxybut-2-en-1-ylprop-2-ynoate 在 silver hexafluoroantimonate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 硼烷四氢呋喃络合物 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 22.17h， 生成 (S)-2-(4-methylene-5-oxotetrahydrofuran-3-yl)ethyl (4-methoxyphenyl)carbamate
  参考文献：
  名称：

  Synthesis and evaluation of new α-methylene-γ-lactone carbamates with NO production inhibitory effects in lipopolysaccharide-induced RAW 264.7 macrophages

  摘要：

  A series of new alpha-methylene-gamma-lactone carbamates were synthesized by an asymmetric synthetic route. The activities on inhibiting nitric oxide (NO) release of these compounds were evaluated in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. The results indicated that most of the compounds except one exhibited potent NO inhibitory effect with IC50 value more than 2 mu M. The cytotoxicities of these compounds were estimated via MTT assays. The results suggested that six compounds were accompanied by low cytotoxicity. The structure activity relationships were also discussed. The S configuration of C3 on lactones ring would be more helpful to NO inhibitory effect. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.016

文献信息

• 异氰酸酯、苯甲酸及肉桂酸取代的滇南洋耳菊 内酯类似物及其合成与应用
  申请人：中国人民解放军第二军医大学

  公开号：CN104926761B

  公开（公告）日：2017-03-29

  本发明涉及医药技术领域，本发明提供了一类异氰酸酯、苯甲酸及肉桂酸取代的滇南洋耳菊内酯类似物，本发明还提供了上述滇南洋耳菊内酯类似物合成方法与在制备抗炎药物中的应用。本发明化合物经细胞抗炎活性及细胞毒性实验，结果证明，本发明化合物具有很好的抑制巨噬细胞RAW264.7产生NO的活性；且细胞毒性较低。因此，本发明化合物具有较好的抗炎活性，并且存在低毒性化合物，可作为新的抗炎药物。
• Synthesis and evaluation of new α-methylene-γ-lactone carbamates with NO production inhibitory effects in lipopolysaccharide-induced RAW 264.7 macrophages
  作者：Wen-Hao Shao、Bing-Yang Chen、Xiang-Rong Cheng、Hu Yuan、Hao Chen、Wan-Lin Chang、Ji Ye、Shan Lin、Qing-Yan Sun、Wei-Dong Zhang

  DOI：10.1016/j.ejmech.2015.02.016

  日期：2015.3

  A series of new alpha-methylene-gamma-lactone carbamates were synthesized by an asymmetric synthetic route. The activities on inhibiting nitric oxide (NO) release of these compounds were evaluated in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. The results indicated that most of the compounds except one exhibited potent NO inhibitory effect with IC50 value more than 2 mu M. The cytotoxicities of these compounds were estimated via MTT assays. The results suggested that six compounds were accompanied by low cytotoxicity. The structure activity relationships were also discussed. The S configuration of C3 on lactones ring would be more helpful to NO inhibitory effect. (C) 2015 Elsevier Masson SAS. All rights reserved.