(6aS,12aS,5'R)-12-deoxy-6',7'-dihydro-7'-methanesulfonylrotenone | 253785-52-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: (6aS,12aS,5'R)-12-deoxy-6',7'-dihydro-7'-methanesulfonylrotenone
• 英文别名: 2-[(1S,6R,13S)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-6-yl]propyl methanesulfonate
• CAS: 253785-52-3
• 化学式: C₂₄H₂₈O₈S
• 分子量: 476.548
• InChiKey: ORMXCBPIDLFUAH-FQUPUIAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6aS,12aS,5'R)-12-deoxy-6',7'-dihydro-7'-methanesulfonylrotenone 在 potassium [¹⁸F]fluoride 作用下， 以 乙腈 为溶剂， 反应 0.2h， 生成 [18F](6aS,12aS,5'R)-12-deoxy-6',7'-dihydro-7'-fluororotenone
  参考文献：
  名称：

  Synthesis and evaluation of a new fluorine-18 labeled rotenoid as a potential PET probe of mitochondrial complex I activity

  摘要：

  Fluorine-18 labeled (6aS, 12aS, 5'R)-12-deoxo-6',7'-dihydro-7'-fluororote (F-DDRT), a new potential PET probe of mitochondrial complex I activity, was synthesized. [F-18]-DDRT was prepared with good specific activity by nucleophilic displacement with an overall radiochemical yield of 25% (EOB). The uptake of [F-18]-DDRT in rat brain and heart was compared with the uptake of another fluorine-18 labeled rotenoid: [F-18]-DHRT. In comparison to [F-18]-DHRT, the brain and heart retention of [F-18]-DDRT were both lower at any point of the study (respectively 0.49 and 2.82% dose/g vs 0.34 and 1.24% dose/g at 60 min post injection).

  DOI：

  10.1002/(sici)1099-1344(199911)42:11<1039::aid-jlcr259>3.0.co;2-1
• 作为产物：
  描述：

  (6aS,12aS,5'R)-鱼藤酮烯醇乙酸酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 9-borabicyclo[3.3.1]nonane dimer 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.5h， 生成 (6aS,12aS,5'R)-12-deoxy-6',7'-dihydro-7'-methanesulfonylrotenone
  参考文献：
  名称：

  Synthesis and evaluation of a new fluorine-18 labeled rotenoid as a potential PET probe of mitochondrial complex I activity

  摘要：

  Fluorine-18 labeled (6aS, 12aS, 5'R)-12-deoxo-6',7'-dihydro-7'-fluororote (F-DDRT), a new potential PET probe of mitochondrial complex I activity, was synthesized. [F-18]-DDRT was prepared with good specific activity by nucleophilic displacement with an overall radiochemical yield of 25% (EOB). The uptake of [F-18]-DDRT in rat brain and heart was compared with the uptake of another fluorine-18 labeled rotenoid: [F-18]-DHRT. In comparison to [F-18]-DHRT, the brain and heart retention of [F-18]-DDRT were both lower at any point of the study (respectively 0.49 and 2.82% dose/g vs 0.34 and 1.24% dose/g at 60 min post injection).

  DOI：

  10.1002/(sici)1099-1344(199911)42:11<1039::aid-jlcr259>3.0.co;2-1

文献信息

• Martarello; Greenamyre; Goodman, Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S494-S496
  作者：Martarello、Greenamyre、Goodman

  DOI：——

  日期：——