3-O-3'-methylbutyl-4a,10a-dihydrofusarubin A

• 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: 3-O-3'-methylbutyl-4a,10a-dihydrofusarubin A
• 英文别名: (3R,4aR,10aS)-6,9-dihydroxy-7-methoxy-3-methyl-3-(3-methylbutoxy)-1,4,4a,10a-tetrahydrobenzo[g]isochromene-5,10-dione
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: AOPGIFKQYFONDP-FKANQGBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  异戊醇 、 3-O-butyl-4a,10a-dihydrofusarubin A 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以4.1 mg的产率得到3-O-3'-methylbutyl-4a,10a-dihydrofusarubin A
  参考文献：
  名称：

  New 3-<i>O</i>-Alkyl-4a,10a-dihydrofusarubins Produced by <i>Fusarium</i> sp. Mj-2

  摘要：

  Five new 3-O-alkyl-4a,10a-dihydrofusarubins (2-6) were isolated from the culture filtrate of a strain of Fusarium sp. (Mj-2), together with the known metabolite, anhydrofusarubin (1). The structures of the new metabolites were elucidated by spectroscopic analyses to be 3-O-butyl, 3-O-3'-methylbutyl, 3-O-2'-methylbutyl and 3-O-2'-phenylethyl-4a,10a-dihydrofusarubin A, and an isomer of 3-O-2'-phenylethyl-4a,10a-dihydrofusarubin A. Their antifungal and antibacterial activities were evaluated together with a 3-O-methyl derivative (7) prepared from 3-O-butyl-4a,10a-dihydrofusarubin A (2), indicating that the size of the O-substituent at C-3 in the 4a,10a-dihydrofusarubins negatively affected the metabolites' antimicrobial activity.

  DOI：

  10.1271/bbb.120670

文献信息

• New 3-&lt;i&gt;O&lt;/i&gt;-Alkyl-4a,10a-dihydrofusarubins Produced by &lt;i&gt;Fusarium&lt;/i&gt; sp. Mj-2
  作者：Masanobu SUZUKI、Naoto NISHIDA、Atsushi ISHIHARA、Hiromitsu NAKAJIMA

  DOI：10.1271/bbb.120670

  日期：——

  Five new 3-O-alkyl-4a,10a-dihydrofusarubins (2-6) were isolated from the culture filtrate of a strain of Fusarium sp. (Mj-2), together with the known metabolite, anhydrofusarubin (1). The structures of the new metabolites were elucidated by spectroscopic analyses to be 3-O-butyl, 3-O-3'-methylbutyl, 3-O-2'-methylbutyl and 3-O-2'-phenylethyl-4a,10a-dihydrofusarubin A, and an isomer of 3-O-2'-phenylethyl-4a,10a-dihydrofusarubin A. Their antifungal and antibacterial activities were evaluated together with a 3-O-methyl derivative (7) prepared from 3-O-butyl-4a,10a-dihydrofusarubin A (2), indicating that the size of the O-substituent at C-3 in the 4a,10a-dihydrofusarubins negatively affected the metabolites' antimicrobial activity.