(-)-2-O-desmethyl-6',7'-dihydroroten-12α-ol | 167491-03-4

• 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: (-)-2-O-desmethyl-6',7'-dihydroroten-12α-ol
• 英文别名: (1S,6R,12S,13R)-17-methoxy-6-propan-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene-12,16-diol
• CAS: 167491-03-4
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: YQRSMOBZEPKGNB-RZXSNQJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-2-O-desmethyl-6',7'-dihydroroten-12α-ol 在 四丁基氢氧化铵 、 pyridinium chlorochromate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,6aS,12aS)-8-(2-Fluoro-ethoxy)-2-isopropyl-9-methoxy-1,2,12,12a-tetrahydro-6aH-chromeno[3,4-b]furo[2,3-h]chromen-6-one
  参考文献：
  名称：

  Martarello; Greenamyre; Goodman, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S558-S560

  摘要：

  DOI：
• 作为产物：
  描述：

  (6aS,12S,12aR,5′R)-12-deoxo-12-hydroxyrotenone 在 palladium on activated charcoal 氢气 、 mesna 、 2,4-滴二甲胺盐 作用下， 生成 (-)-2-O-desmethyl-6',7'-dihydroroten-12α-ol
  参考文献：
  名称：

  Martarello; Greenamyre; Goodman, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S558-S560

  摘要：

  DOI：

文献信息

• (−)-6′,7′-[11C]Dihydroroten-12α-ol ((−)-[11C]DHROL) forin vivo measurement of mitochondrial Complex I
  作者：Scott E. Snyder、Phillip S. Sherman、Timothy J. Desmond、Kirk A. Frey、Michael R. Kilbourn

  DOI：10.1002/(sici)1099-1344(199907)42:7<641::aid-jlcr226>3.0.co;2-y

  日期：1999.7

  Deficits in Complex I (NADH-ubiquinone oxidoreductase) of the electron transport chain may play an important role in the inception and progression of neurodegenerative diseases such as Parkinson's disease. In vivo imaging of Complex I offers a unique method for evaluation of these changes in living human brain. Previous carbon-11 labeled rotenoids showed promising results, but were prepared as mixtures of stereoisomers at the 5'-position. We report here the stereospecific syntheses of (-)-6',7'-[C-11]dihydroroten-12 alpha-ol ((-)-[C-11]DHROL), a modified rotenoid with in vitro affinity for Complex I. O-[C-11]methylation of the appropriate desmethyl precursor provided (-)-[C-11]DHROL in an average radiochemical yield, corrected to end of bombardment, of 27% (n = 4) and >99% radiochemical purity. In mice, (-)-[C-11]DHROL gave a high and uniform brain uptake similar to that obtained with prior radiolabeled rotenoids. Further in vivo evaluation of (-)-[C-11]DHROL in rats with unilateral quinolinic acid-induced striatal lesions showed significant losses of radioligand binding after neurotoxin treatment (lesion/unlesioned ratio of 0.66). As this reduction of in vivo radioligand binding is very similar to that obtained previously with the mixture of [C-11]DHROL isomers, the stereochemistry at the 5'-position of [C-11]DHROL does not significantly influence the in vivo applications of this radiotracer.