WF 11 | 152783-29-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: WF 11
• 英文别名: 8-methyl-2β-propanoyl-3β-p-tolyl-8-azabicyclo<3.2.1>octane；WF-11；2-Propanoyl-3-(4-tolyl)tropane；1-[(1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octan-2-yl]propan-1-one
• CAS: 152783-29-4
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: PZEAJTAVRYLBTK-LHHMISFZSA-N

物化性质

• 沸点：
  389.1±42.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  富马酸 、 WF 11 以 异丙醇 为溶剂， 以81%的产率得到8-methyl-2β-propanoyl-3β-(4-methylphenyl)-8-azabicyclo[3.2.1]octane fumarate
  参考文献：
  名称：

  Hemby; Lucki; Gatto, Journal of Pharmacology and Experimental Therapeutics, 1997, vol. 282, # 2, p. 727 - 733

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯基溴化镁 、 8-methyl-2-propanoyl-8-azabicyclo<3.2.1>oct-2-ene 在 copper bromide-dimethyl sulfide 作用下， 以 乙醚 为溶剂， 生成 WF 11 、 8-methyl-2α-propanoyl-3β-p-tolyl-8-azabicyclo<3.2.1>octane
  参考文献：
  名称：

  Synthesis of 2.beta.-Acyl-3.beta.-aryl-8-azabicyclo[3.2.1]octanes and Their Binding Affinities at Dopamine and Serotonin Transport Sites in Rat Striatum and Frontal Cortex

  摘要：

  A novel entry to tropane analogs of cocaine was developed on the basis of the reaction of rhodium-stabilized vinylcarbenoids with pyrroles. These analogs were tested:in binding to dopamine and serotonin (5-HT) transporters in:membranes from rat striatum and frontal cortex. In all the analogs, the aryl group at the 3-position was directly bound to the tropane ring (as in WIN-35,428), and methyl or ethyl ketone moieties were present at the a-position instead of the typical ester group. The series of analogs containing a 2-naphthyl group at the 3-position were most potent, with K-i values < 1 nM in binding to both dopamine and 5-HT transporters. Although the unsubstituted 2-naphthyl analog was nonselective at dopamine and 5-HT transport sites, other compounds:were selective for either site. In general, compounds with relatively small substituents on the aromatic moiety (such as p-methyl or p-fluoro) were relatively selective for the dopamine transporters, while a p-isopropylphenyl derivative was selective:for the 5-HT transport sites. This latter compound represents the first N-methyltropane derivative specific for 5-HT transporters. Resolution of two of the most significant analogs was achieved by HPLC on a chiral stationary phase; the active enantiomer of a 2-naphthyl analog exhibited K-i values of <0.1 nM at both dopamine and 5-HT transporter sites.

  DOI：

  10.1021/jm00035a005

文献信息

• A MEDICAL FLUID, A METHOD OF TREATMENT AND USE OF THE FLUID
  申请人：XVIVO Perfusion AB

  公开号：EP2568805B1

  公开（公告）日：2019-05-01