(S)-5-((R,4'E,8'E)-1'-hydroxy-5',9',13'-trimethyltetradeca-4',8',12'-trien-1'-yl)-5-methyldihydrofuran-2(3H)-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-5-((R,4'E,8'E)-1'-hydroxy-5',9',13'-trimethyltetradeca-4',8',12'-trien-1'-yl)-5-methyldihydrofuran-2(3H)-one
• 英文别名: (5S)-5-[(1R,4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trienyl]-5-methyloxolan-2-one
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: FMCVIMRVTTZJJB-HXNVHFGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  <(2E)-6-Hydroxy-3-methyl-2-hexenyl>acetat 在 吡啶 、 咪唑 、 chromium(VI) oxide 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 六甲基磷酰三胺 、 sodium chlorite 、 正丁基锂 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 L-(+)-酒石酸二乙酯 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 癸烷 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 52.17h， 生成 (S)-5-((R,4'E,8'E)-1'-hydroxy-5',9',13'-trimethyltetradeca-4',8',12'-trien-1'-yl)-5-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors

  摘要：

  Nafuredin-gamma (2), converted from nafuredin (1) under mild basic conditions, demonstrates potent and selective inhibitory activity against helminth complex I. However, 2 is unstable in air because the conjugated dienes are oxygen-labile. To address this, we designed and synthesized air-stable nafuredin-gamma analogs. Although the complex I inhibitory activities of all the new nafuredin-gamma analogs were lower than that of 2, all were in the high nM range (IC50: 300-820 nM). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.030

文献信息

• Design, synthesis, and biological evaluation of air-stable nafuredin-γ analogs as complex I inhibitors
  作者：Masaki Ohtawa、Mari Matsunaga、Keiko Fukunaga、Risa Shimizu、Eri Shimizu、Shiho Arima、Junko Ohmori、Kiyoshi Kita、Kazuro Shiomi、Satoshi Omura、Tohru Nagamitsu

  DOI：10.1016/j.bmc.2015.01.030

  日期：2015.3

  Nafuredin-gamma (2), converted from nafuredin (1) under mild basic conditions, demonstrates potent and selective inhibitory activity against helminth complex I. However, 2 is unstable in air because the conjugated dienes are oxygen-labile. To address this, we designed and synthesized air-stable nafuredin-gamma analogs. Although the complex I inhibitory activities of all the new nafuredin-gamma analogs were lower than that of 2, all were in the high nM range (IC50: 300-820 nM). (C) 2015 Elsevier Ltd. All rights reserved.