5-butyl-8,9-methylenedioxy-4-vinyl-5,6-dihydrophenantridine | 919535-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-butyl-8,9-methylenedioxy-4-vinyl-5,6-dihydrophenantridine
• 英文别名: 5-Butyl-8,9-methylenedioxy-4-vinyl-5,6-dihydrophenanthridine；5-butyl-4-ethenyl-6H-[1,3]dioxolo[4,5-j]phenanthridine
• CAS: 919535-79-8
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: GYFLMAMWMPHENC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-butyl-8,9-methylenedioxy-4-vinyl-5,6-dihydrophenantridine 在 palladium on activated charcoal 氢气 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 以61%的产率得到4-butyl-5-methyl-8,9-methylenedioxy-5,6-dihydrophenantridine
  参考文献：
  名称：

  制备针对乙酰胆碱酯酶的椰油糖皮质激素。

  摘要：

  通过化学转化，主要由N-烷基化，霍夫曼降解型反应，三氯乙基羰基部分的还原裂解和氢化等化学转化反应，轻松地从lycorine制备出具有5,6-二氢菲啶骨架的5,6-二糖皮质激素。数个二十碳椰油碱衍生物显示出对乙酰胆碱酯酶的有效抑制活性，IC（50）值在微摩尔范围内，并且比加兰他敏更有效。

  DOI：

  10.1016/j.bmc.2006.10.026
• 作为产物：
  描述：

  石蒜碱 在 吡啶 、 potassium tert-butylate 作用下， 以 乙腈 、 叔丁醇 为溶剂， 反应 46.0h， 生成 5-butyl-8,9-methylenedioxy-4-vinyl-5,6-dihydrophenantridine
  参考文献：
  名称：

  制备针对乙酰胆碱酯酶的椰油糖皮质激素。

  摘要：

  通过化学转化，主要由N-烷基化，霍夫曼降解型反应，三氯乙基羰基部分的还原裂解和氢化等化学转化反应，轻松地从lycorine制备出具有5,6-二氢菲啶骨架的5,6-二糖皮质激素。数个二十碳椰油碱衍生物显示出对乙酰胆碱酯酶的有效抑制活性，IC（50）值在微摩尔范围内，并且比加兰他敏更有效。

  DOI：

  10.1016/j.bmc.2006.10.026

文献信息

• Compond for treatment or prevention of of obesity or diseases related to obesity, and application thereof
  申请人：SHANGHAI INSTITUTES FOR BIOLOGICAL SCIENCES, CHINESE ACADEMY OF SCIENCES

  公开号：US20200385396A1

  公开（公告）日：2020-12-10

  A compound for treatment or prevention of obesity or diseases related to obesity, and an application thereof. Specifically, provided are a compound as represented by formula I, or a pharmaceutically-acceptable salt thereof, and a pharmaceutical composition containing the compound. The compound has multiple functions and can be used for treatment or prevention of obesity or diseases related to obesity.
• Preparation of secolycorines against acetylcholinesterase
  作者：Shoei-Sheng Lee、Uppala Venkatesham、Chitneni Prasad Rao、Sio-Hong Lam、Jung-Hsin Lin

  DOI：10.1016/j.bmc.2006.10.026

  日期：2007.1

  5,6-Secolycorines possessing a 5,6-dihydrophenanthridine skeleton were facilely prepared from lycorine through chemical transformations, mainly including N-alkylation, Hofmann degradation type reaction, reductive cleavage of trichloroethylcarbonyl moiety, and hydrogenation. Several secolycorine derivatives showed potent inhibitory activity against acetylcholinesterase with the IC(50) value at micromolar

  通过化学转化，主要由N-烷基化，霍夫曼降解型反应，三氯乙基羰基部分的还原裂解和氢化等化学转化反应，轻松地从lycorine制备出具有5,6-二氢菲啶骨架的5,6-二糖皮质激素。数个二十碳椰油碱衍生物显示出对乙酰胆碱酯酶的有效抑制活性，IC（50）值在微摩尔范围内，并且比加兰他敏更有效。
• Synthesis and antiplasmodial activity of lycorine derivatives
  作者：Juan C. Cedrón、David Gutiérrez、Ninoska Flores、Ángel G. Ravelo、Ana Estévez-Braun

  DOI：10.1016/j.bmc.2010.05.023

  日期：2010.7

  Twenty seven lycorine derivatives were prepared and evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum. The best antiplasmodial activities were achieved with lycorine derivatives that present free hydroxyl groups at C-1 and C-2 or esterified as acetates or isobutyrates. The double bond C-2-C-3 is also important for the activity. Concerning to the antiplasmodial activity of the secolycorines, the higher values were obtained with the replacement of the methylenedioxy moiety by hydroxyl or acetate groups and with methyl substituent attached to the nitrogen atom. (C) 2010 Elsevier Ltd. All rights reserved.