4-butyl-2,5-dimethylpyrano[2,3,4-ij]isoquinolin-8-(4H)-one | 1202043-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-butyl-2,5-dimethylpyrano[2,3,4-ij]isoquinolin-8-(4H)-one
• 英文别名: 6-Butyl-3,7-dimethyl-2-oxa-6-azatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),7,9-pentaen-11-one
• CAS: 1202043-11-5
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: VNABPUBBADDZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-butyl-8-hydroxy-2,5-dimethylpyrano[2,3,4-ij]isoquinolin-4-ium chloride 在 三乙胺 作用下， 以 水 为溶剂， 反应 0.08h， 以67%的产率得到4-butyl-2,5-dimethylpyrano[2,3,4-ij]isoquinolin-8-(4H)-one
  参考文献：
  名称：

  Transformation of barakol into cassiarins A, B, and their derivatives

  摘要：

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.053

文献信息

• Synthesis and structure–activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity
  作者：Hiroshi Morita、Yuichiro Tomizawa、Jun Deguchi、Tokio Ishikawa、Hiroko Arai、Kazumasa Zaima、Takahiro Hosoya、Yusuke Hirasawa、Takayuki Matsumoto、Katsuo Kamata、Wiwied Ekasari、Aty Widyawaruyanti、Tutik Sri Wahyuni、Noor Cholies Zaini、Toshio Honda

  DOI：10.1016/j.bmc.2009.10.013

  日期：2009.12

  Cassiarin A 1, a tricyclic alkaloid, isolated from the leaves of Cassia siamea (Leguminosae), shows powerful antimalarial activity against Plasmodium falciparum in vitro as well as P. berghei in vivo, which may be valuable leads for novel antimalarials. Interactions of parasitized red blood cells (pRBCs) with endothelium in aorta are especially important in the processes contribute to the pathogenesis

  从决明子（Lesiaminosae）的叶子中分离出的三环生物碱Cassiarin A 1对恶性疟原虫和体内的伯氏疟原虫具有强大的抗疟疾活性，这可能是新型抗疟疾的有价值的线索。在导致严重疟疾发病机理的过程中，被寄生的红细胞（pRBC）与主动脉内皮的相互作用尤为重要。一氧化氮（NO）减少了pRBC粘附于血管内皮的受体/粘附分子的内皮表达，并降低了pRBC对血管内皮的细胞粘附。决明A 1表现出对大鼠主动脉环的血管舒张活性，这可能与一氧化氮的产生有关。一系列的羟基和氮取代的衍生物和的脱衍生物的1已被合成为具有针对有效的抗疟药恶性疟原虫具有血管舒张活性，这可以减少的pRBC的细胞粘连至血管内皮。决明子A 1在体外表现出有效的抗疟疾活性和高选择性指数，表明没有任何取代基的羟基和氮原子的存在对于显示抗疟疾活性可能很重要。相对于决明子A，甲氧基衍生物显示出更强的血管舒张活性，尽管它并未显示出对恶性疟原虫抑
• Transformation of barakol into cassiarins A, B, and their derivatives
  作者：Sarawut Kanputhorn、Amorn Petsom、Patchanita Thamyongkit

  DOI：10.1016/j.tet.2010.07.053

  日期：2010.9

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.