C34-epi-C35-trifluorosolamin | 1423740-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: C34-epi-C35-trifluorosolamin
• 英文别名: (2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2-(trifluoromethyl)-2H-furan-5-one
• CAS: 1423740-70-8
• 化学式: C₃₅H₆₁F₃O₅
• 分子量: 618.862
• InChiKey: ITAFHFMNKNBLSD-UPYFENACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  43
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (8R,9R,12R,13R)-13-(tert-butyldimethylsilyloxy)-9,12-epoxy-pentacosa-1,6-diyn-8-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Wilkinson's catalyst 、 氢氟酸 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 苯 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 生成 C34-epi-C35-trifluorosolamin
  参考文献：
  名称：

  Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I

  摘要：

  C34-epi and C34-epi-C35-trifluoro analogues of solamin, a mono-THF annonaceous acetogenin, were synthesized. Their inhibitory activity, along with previously synthesized analogues (C35-fluoro, C35-difluoro, and C35-trifluorosolamins), against bovine mitochondrial NADH-ubiquinone oxidoreductase (complex I) was determined. The present study revealed that the methyl group on the gamma-lactone moiety is critical to the potent inhibition of complex I by natural acetogenins. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.018

文献信息

• Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I
  作者：Naoto Kojima、Masato Abe、Yuki Suga、Kazufumi Ohtsuki、Tetsuaki Tanaka、Hiroki Iwasaki、Masayuki Yamashita、Hideto Miyoshi

  DOI：10.1016/j.bmcl.2013.01.018

  日期：2013.3

  C34-epi and C34-epi-C35-trifluoro analogues of solamin, a mono-THF annonaceous acetogenin, were synthesized. Their inhibitory activity, along with previously synthesized analogues (C35-fluoro, C35-difluoro, and C35-trifluorosolamins), against bovine mitochondrial NADH-ubiquinone oxidoreductase (complex I) was determined. The present study revealed that the methyl group on the gamma-lactone moiety is critical to the potent inhibition of complex I by natural acetogenins. (c) 2013 Elsevier Ltd. All rights reserved.