N-{[4-(4-Fluorophenyl)-4-oxo]butyl}cytisine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: N-{[4-(4-Fluorophenyl)-4-oxo]butyl}cytisine
• 英文别名: (1R,5S)-3-[4-(4-Fluoro-phenyl)-4-oxo-butyl]-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one；(1R,9S)-11-[4-(4-fluorophenyl)-4-oxobutyl]-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• 化学式: C₂₁H₂₃FN₂O₂
• 分子量: 354.424
• InChiKey: NMIDWQFQCDTCMT-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯-4'-氟苯丁酮 、 cytisine 以 various solvent(s) 为溶剂， 以28%的产率得到N-{[4-(4-Fluorophenyl)-4-oxo]butyl}cytisine
  参考文献：
  名称：

  Synthesis and preliminary pharmacological evaluation of some cytisine derivatives

  摘要：

  Thirty-one N-derivatives of cytisine were prepared in order to modify its pharmacological profile and to obtain compounds of potential therapeutic interest either at a peripheral or central level, particularly as nicotinic ligands with improved ability to cross the blood-brain barrier. Actually, with the introduction of different kinds of substituent on the basic nitrogen of cytisine a variety of activities were observed, both in vivo (analgesic, dopamine antagonism, antihypertensive, inhibition of stress-induced ulcers, antiinflammatory, protection from PAF-induced mortality, hypoglycemic) and in vitro (positive cardio-inotropic, beta-adrenergic antagonism, alpha(1)- and alpha(2)-antagonism, inhibition of PAF-induced platelet aggregation). Six randomly selected compounds were tested for the ability to recognize a central nicotinic receptor and four of them exhibited K-i values; In the range 30-163 nM. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00049-x