5-acetoxy-3,4-dehydro-7,9-dimethoxy-3-methylnaphtho[2,3-c]pyran-10-ol | 959773-72-9

• 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-acetoxy-3,4-dehydro-7,9-dimethoxy-3-methylnaphtho[2,3-c]pyran-10-ol
• 英文别名: (10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-5-yl) acetate
• CAS: 959773-72-9
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: WTEXBTGYHLFIFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-acetoxy-3,4-dehydro-7,9-dimethoxy-3-methylnaphtho[2,3-c]pyran-10-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以4.4 mg的产率得到3,4-dehydro-5,10-diacetyloxy-7,9-dimethoxy-3-methylnaphtho[2,3-c]pyran
  参考文献：
  名称：

  Heptaketides from Corynespora sp. Inhabiting the Cavern Beard Lichen, Usnea cavernosa: First Report of Metabolites of an Endolichenic Fungus

  摘要：

  Two new heptaketides, corynesporol (1) and l-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of I afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.

  DOI：

  10.1021/np070466w
• 作为产物：
  描述：

  乙酸酐 、 3,4-二氢-3-羟基-7,9-二甲氧基-3-甲基-1H-萘并[2,3-c]吡喃-5,10-二酮 在 sodium acetate 、 溶剂黄146 、 锌 作用下， 反应 0.75h， 以6.0 mg的产率得到5-acetoxy-3,4-dehydro-7,9-dimethoxy-3-methylnaphtho[2,3-c]pyran-10-ol
  参考文献：
  名称：

  Heptaketides from Corynespora sp. Inhabiting the Cavern Beard Lichen, Usnea cavernosa: First Report of Metabolites of an Endolichenic Fungus

  摘要：

  Two new heptaketides, corynesporol (1) and l-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of I afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.

  DOI：

  10.1021/np070466w

文献信息

• Heptaketides from <i>Corynespora</i> sp. Inhabiting the Cavern Beard Lichen, <i>Usnea cavernosa</i>: First Report of Metabolites of an Endolichenic Fungus
  作者：Priyani A. Paranagama、E. M. Kithsiri Wijeratne、Anna M. Burns、Marilyn T. Marron、Malkanthi K. Gunatilaka、A. Elizabeth Arnold、A. A. Leslie Gunatilaka

  DOI：10.1021/np070466w

  日期：2007.11.1

  Two new heptaketides, corynesporol (1) and l-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of I afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.