3-dodecyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one | 249906-77-2

• 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: 3-dodecyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
• 英文别名: (1R,9S)-11-dodecyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• CAS: 249906-77-2
• 化学式: C₂₃H₃₈N₂O
• 分子量: 358.568
• InChiKey: HGZHHBCHIUPZGR-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴代十二烷 、 cytisine 反应 6.0h， 以61%的产率得到3-dodecyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
  参考文献：
  名称：

  N-烷基胞苷的高效合成方法

  摘要：

  Cytisine 及其衍生物因其广泛的生物活性而受到许多研究人员的青睐，例如，解痉、杀虫、胆碱能、镇痛等 [1-7]。因此，生物碱胞嘧啶及其衍生物是有前景的化合物，可用于基于它们的新药的可能修饰和设计。在本文中，交流了在仲胺处烷基化胞嘧啶的便捷方法的开发。通过将混合物在 150°C 下加热 6 小时，由胞嘧啶、壬基碘和十二烷基溴合成化合物 1a、b。在各种溶剂（DMSO、DMF、邻二甲苯）中长时间回流形成 1a、b，产率 <20%，同时含有未知副产物的混合物。

  DOI：

  10.1007/s10600-019-02703-w

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.