N-[(2-Hydroxy-2-phenyl)ethyl]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-[(2-Hydroxy-2-phenyl)ethyl]cytisine
• 英文别名: N-(2-hydroxy-2-phenylethyl)cytisine；(1R,9S)-11-(2-hydroxy-2-phenylethyl)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: WIVHHJZQKWCBGX-QJZXMCBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-phenyl-2-(cytisin-12-yl)-1-ethanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到N-[(2-Hydroxy-2-phenyl)ethyl]cytisine
  参考文献：
  名称：

  Synthesis and biological activity of N-(2-hydroxyethyl)cytisine derivatives

  摘要：

  通过还原 N-(2-羟乙基)胞嘧啶、N-(2-羟丙基)胞嘧啶、N-(2-羟基-2-(1-金刚烷基)乙基)胞嘧啶和 N-(2-羟基-2-苯乙基)胞嘧啶，合成了 N-(2-羟乙基)胞嘧啶的衍生物、由 N-(2-氧代丙基)-、N-(2-氧代-2-(1-金刚烷基)乙基)-和 N-(2-氧代-2-苯基乙基)胞嘧啶与金属氢化物还原合成。研究了所制备化合物的抗心律失常和镇痛活性。

  DOI：

  10.1007/s10600-007-0076-3

文献信息

• 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.
• Synthesis and biological activity of N-(2-hydroxyethyl)cytisine derivatives
  作者：D. V. Shishkin、A. R. Shaimuratova、A. N. Lobov、N. Z. Baibulatova、L. V. Spirikhin、M. S. Yunusov、N. S. Makara、N. Zh. Baschenko、V. A. Dokichev

  DOI：10.1007/s10600-007-0076-3

  日期：2007.3

  Derivatives of N-(2-hydroxyethyl)cytisine, N-(2-hydroxypropyl)-, N-(2-hydroxy-2-(1-adamantyl)ethyl)-, and N-(2-hydroxy-2-phenylethyl)cytisine, were synthesized by reduction of N-(2-oxopropyl)-, N-(2-oxo-2-(1-adamantyl)ethyl)-and N-(2-oxo-2-phenylethyl)cytisine with metal hydrides. The antiarrhythmic and analgesic activities of the prepared compounds were investigated.

  通过还原 N-(2-羟乙基)胞嘧啶、N-(2-羟丙基)胞嘧啶、N-(2-羟基-2-(1-金刚烷基)乙基)胞嘧啶和 N-(2-羟基-2-苯乙基)胞嘧啶，合成了 N-(2-羟乙基)胞嘧啶的衍生物、由 N-(2-氧代丙基)-、N-(2-氧代-2-(1-金刚烷基)乙基)-和 N-(2-氧代-2-苯基乙基)胞嘧啶与金属氢化物还原合成。研究了所制备化合物的抗心律失常和镇痛活性。