5-methyl-4-vinyl-5,6-dihydrophenanthridine-8,9-diol | 1239874-79-3

• 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-methyl-4-vinyl-5,6-dihydrophenanthridine-8,9-diol
• 英文别名: 4-ethenyl-5-methyl-5,6-dihydrophenanthridine-8,9-diphenol；4-ethenyl-5-methyl-5,6-dihydrophenanthridine-8,9-diol；8,9-dihydroxy-5-methyl-4-vinyl-5,6-dihydrophenantridine；4-ethenyl-5-methyl-6H-phenanthridine-8,9-diol
• CAS: 1239874-79-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: HQPNGRNJFCOGLU-UHFFFAOYSA-N

物化性质

• 沸点：
  498.5±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  月桂酰氯 、 5-methyl-4-vinyl-5,6-dihydrophenanthridine-8,9-diol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以77%的产率得到8,9-dilauroyloxy-5-methyl-4-vinyl-5,6-dihydrophenantridine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of lycorine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.05.023
• 作为产物：
  描述：

  5-methyl-4-vinyl-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine 在 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 5-methyl-4-vinyl-5,6-dihydrophenanthridine-8,9-diol
  参考文献：
  名称：

  菲啶类化合物在农药上的应用

  摘要：

  本发明涉及含有通式(1)代表的菲啶类化合物在农药上的应用，其中部分化合物用作植物病毒剂，能很好的抑制烟草花叶病毒；用作杀菌剂，对番茄早疫、小麦赤霉、马铃薯晚疫、辣椒疫霉、油菜菌核、黄瓜灰霉、水稻纹枯、黄瓜枯萎、花生褐斑、苹果轮纹、小麦纹枯、玉米小斑、西瓜炭疽、水稻恶苗都有很好的抑制活性；用作杀虫剂对粘虫、蚊幼虫、棉铃虫、玉米螟、蚜虫、成螨和小菜蛾有毒杀活性。式中，当分子的氮不为亚胺时为R1可代表氢原子，甲基，乙酰基，苯甲酰基；R2和R3同时代表氢原子或氧原子；R4和R5可代表羟基，乙酰氧基，甲氧基，亚甲氧基，氟原子，氢原子；R6为溴原子或氟原子；R7为氢原子或乙烯基。当氮为亚胺时R1不代表任何基团；R3和R2其中一个不代表任何基团，另一个可代表氢原子，甲氧基，乙氧基，苯甲氧基，氯原子；R4、R5、R6、R7都代表氢原子。

  公开号：

  CN110074124B

文献信息

• Phenanthridine Derivatives, Preparation Methods and Uses Thereof
  申请人：Kunming Institute of Botany, The Chinese Academy of Sciences

  公开号：US20160083364A1

  公开（公告）日：2016-03-24

  The present invention relates to the pharmaceutical field, in particular to a phenanthridine derivative as shown in general formula (1) a pharmaceutical composition comprising the derivative, its preparation method, and its uses in manufacture of a medicament for the prevention or treatment of a disease related to the activity of Wnt signaling pathway, hepatitis C and hepatitis B.

  本发明涉及制药领域，特别是一种如通用式（1）所示的苯并三氮杂环衍生物，包括该衍生物的药物组合物、其制备方法，以及其在制备与Wnt信号通路活性、丙型肝炎和乙型肝炎相关疾病的预防或治疗药物中的用途。
• COMPOUND FOR TREATMENT OR PREVENTION 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：EP3685838A1

  公开（公告）日：2020-07-29

  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.

  一种用于治疗或预防肥胖或与肥胖有关的疾病的化合物及其应用。具体而言，提供了一种由式 I 代表的化合物或其药学上可接受的盐，以及含有该化合物的药物组合物。该化合物具有多种功能，可用于治疗或预防肥胖或与肥胖相关的疾病。
• [EN] PHENANTHRIDINE DERIVATIVES, PREPARATION METHODS THEREFOR AND USES THEREOF<br/>[FR] DÉRIVÉS DE PHÉNANTHRIDINE, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS
  申请人：KUNMING INST OF BOTANY THE CHINESE ACADEMY OF SCIENCES

  公开号：WO2014131368A1

  公开（公告）日：2014-09-04

  提供了通式（I）所示的菲啶类衍生物、包含该衍生物的药物组合物、其制备方法及其在制备预防或治疗与Wnt信号通路活性的相关疾病、丙型肝炎和乙型肝炎的药物中的用途。
• EP3685838
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, Synthesis, and Structural Optimization of Lycorine-Derived Phenanthridine Derivatives as Wnt/β-Catenin Signaling Pathway Agonists
  作者：Duo-Zhi Chen、Chen-Xu Jing、Jie-Yun Cai、Ji-Bo Wu、Sheng Wang、Jun-Lin Yin、Xiao-Nian Li、Lin Li、Xiao-Jiang Hao

  DOI：10.1021/acs.jnatprod.5b00825

  日期：2016.1.22

  Lycorine is a benzylphenethylamine-type alkaloid member of the Amaryllidaceae family. A lycorine derivative, HLY78, was previously identified as a new Wnt/beta-catenin signaling pathway agonist that targets the DAX domain of axin. Herein, the structural optimization of HLY78 and analyses of the structure-activity relationships of lycorine-derived phenanthridine derivatives as agonists of the Wnt/beta-catenin signaling pathway are presented. This research suggests that triazole groups are important pharmacophores for Wnt activation; triazole groups at C-8 and C-9 of phenanthridine compounds markedly enhanced Wnt activation. A C-11-C-12 single bond is also important for Wnt activation. On the basis of these findings, two Wnt agonists were designed and synthesized. The results for these agonists indicated that the combination of a 4-ethyldihydrophenanthridine skeleton and a triazole substituent improves Wnt activation. These compounds may be useful in further pharmacological or biological studies.