(-)-N-(3-oxobutyl)-cytisine | 64408-08-8

• 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-(3-oxobutyl)-cytisine
• 英文别名: (-)-N-(3-oxobutyl)cytisine；N-(3-oxobutyl)cytisine；(1R,5S)-3-(3-Oxo-butyl)-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one；(1R,9S)-11-(3-oxobutyl)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• CAS: 64408-08-8
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: XXSOVMSTJJYBOO-QWHCGFSZSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  490.7±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁烯酮 、 cytisine 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以90%的产率得到(-)-N-(3-oxobutyl)-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

文献信息

• Reaction of cytisine with formalin
  作者：Sh. B. Rakhimov、A. S. Shashkov、V. I. Vinogradova

  DOI：10.1007/s10600-006-0259-3

  日期：2006.11

  The reaction of cytisine with formalin in various solvents was studied. Methylene-bis-cytisine was produced in addition to the expected N-methylolcytisine in all solvents except acetone, in which N-(3-oxobutyl)cytisine was produced.

  研究了细胞素与福尔马林在各种溶剂中的反应。除了预期的N-羟甲基细胞素外，在所有溶剂中均产生了亚甲基双细胞素，但在丙酮中则产生了N-(3-氧代丁基)细胞素。
• Synthesis and preliminary pharmacological evaluation of some cytisine derivatives
  作者：Caterina Canu Boido、Fabio Sparatore

  DOI：10.1016/s0014-827x(99)00049-x

  日期：1999.7

  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.