4,5-didehydroguadiscine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 4,5-didehydroguadiscine
• 英文别名: 16-Methoxy-13,13-dimethyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14(19),15,17-octaene；16-methoxy-13,13-dimethyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14(19),15,17-octaene
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: GLMROMLEFUHTEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(5-methoxy-2-nitrophenyl)-2-methylpropanoate 在 manganese(IV) oxide 、 N-羟基-7-氮杂苯并三氮唑 、 硫酸 、 1,8-双二甲氨基萘 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 、 锌 、 sodium nitrite 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 29.0h， 生成 1-[1-methyl-1-(5-methoxyphenyl)ethyl]-6,7-methylenedioxyisoquinoline 、 4,5-didehydroguadiscine
  参考文献：
  名称：

  Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua

  摘要：

  The first total Synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an alpha,alpha-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported C-13 NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 mu M) of 6 was 40 times stronger than that of arbutin (174 mu M), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor Within this class of compounds.

  DOI：

  10.1021/np500995z

文献信息

• Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, <i>Hornschuchia obliqua</i>
  作者：Genzoh Tanabe、Youta Sugano、Miki Shirato、Naoki Sonoda、Nozomi Tsutsui、Toshio Morikawa、Kiyofumi Ninomiya、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1021/np500995z

  日期：2015.7.24

  The first total Synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an alpha,alpha-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported C-13 NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 mu M) of 6 was 40 times stronger than that of arbutin (174 mu M), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor Within this class of compounds.