5-methoxy-8-methylbenzo[h]coumarin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5-methoxy-8-methylbenzo[h]coumarin
• 英文别名: muralatin A；5-Methoxy-8-methylbenzo[h]chromen-2-one；5-methoxy-8-methylbenzo[h]chromen-2-one
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: CJBHIYZSORBQMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cis-dehydrocoumurrayin 以 四氢呋喃 为溶剂， 反应 24.0h， 以73%的产率得到5-methoxy-8-methylbenzo[h]coumarin
  参考文献：
  名称：

  Anti-inflammatory Coumarin and Benzocoumarin Derivatives from Murraya alata

  摘要：

  Two new rare 8-methylbenzo[h]coumarins, muralatins A and B (1, 2), nine new C-8-substituted coumarins, muralatins CK (3-11), and 22 known analogues (12-33) were isolated from the leaves of Murraya alata. The absolute configurations of compounds 5, 11, 23, 24, 27, 30, and 33 were assigned via comparison of their specific rotations, by Moshers method, and by single-crystal X-ray diffraction and electronic circular dichroism (ECD) data of the in situ formed transition metal complexes. A putative biosynthesis pathway to 1 and 2 is proposed, and the chemical synthesis of 1 was accomplished through electrocyclization of 5,7-dimethoxy-8-[(Z)-3-methylbut-1,3-dienyl)]coumarin (12). Compounds 1, 2, 8, 12, and 31 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 6.014.5 mu M.

  DOI：

  10.1021/np500861u

文献信息

• Anti-inflammatory Coumarin and Benzocoumarin Derivatives from <i>Murraya alata</i>
  作者：Hai-Ning Lv、Shu Wang、Ke-Wu Zeng、Jun Li、Xiao-Yu Guo、Daneel Ferreira、Jordan K. Zjawiony、Peng-Fei Tu、Yong Jiang

  DOI：10.1021/np500861u

  日期：2015.2.27

  Two new rare 8-methylbenzo[h]coumarins, muralatins A and B (1, 2), nine new C-8-substituted coumarins, muralatins CK (3-11), and 22 known analogues (12-33) were isolated from the leaves of Murraya alata. The absolute configurations of compounds 5, 11, 23, 24, 27, 30, and 33 were assigned via comparison of their specific rotations, by Moshers method, and by single-crystal X-ray diffraction and electronic circular dichroism (ECD) data of the in situ formed transition metal complexes. A putative biosynthesis pathway to 1 and 2 is proposed, and the chemical synthesis of 1 was accomplished through electrocyclization of 5,7-dimethoxy-8-[(Z)-3-methylbut-1,3-dienyl)]coumarin (12). Compounds 1, 2, 8, 12, and 31 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 6.014.5 mu M.