3H-Naphtho[1',8a':5,6]pyrano[2,3-e]isoindol-3-one, 1,2,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-5-(phenylmethoxy)-, (6aR,7S,9aS,11S,13aS)- | 189185-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3H-Naphtho[1',8a':5,6]pyrano[2,3-e]isoindol-3-one, 1,2,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-5-(phenylmethoxy)-, (6aR,7S,9aS,11S,13aS)-
• 英文别名: (1S,13R,14S,17S,19S)-19-hydroxy-13,14,18,18-tetramethyl-10-phenylmethoxy-2-oxa-6-azapentacyclo[11.8.0.01,17.03,11.04,8]henicosa-3,8,10-trien-7-one
• CAS: 189185-67-9
• 化学式: C₃₀H₃₇NO₄
• 分子量: 475.628
• InChiKey: QDFDUOFVQKXUIT-OETPTZMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3H-Naphtho[1',8a':5,6]pyrano[2,3-e]isoindol-3-one, 1,2,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-5-(phenylmethoxy)-, (6aR,7S,9aS,11S,13aS)- 在 palladium on activated charcoal sodium tetrahydroborate 、 jones reagent 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 3H-Naphtho[1',8a':5,6]pyrano[2,3-e]isoindol-3-one, 1,2,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5,11-dihydroxy-6a,7,10,10-tetramethyl-, (6aR,7S,9aS,11R,13aS)-
  参考文献：
  名称：

  Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260. II. Synthesis and Preliminary Structure-Activity Relationships of Stachyflin Derivatives.

  摘要：

  研究发现，由水苏芽孢杆菌 RF-7260 产生的水苏碱和乙酰水苏碱具有很强的抗甲型流感病毒活性。水飞蓟素是一类新型的甲型流感病毒血凝素融合抑制剂。研究人员从乙酰水飞蓟素合成了几种衍生物，并对它们的结构-活性关系进行了初步研究。其中，3-氧代和 3，8'-二氧代衍生物显示出与水飞蓟素相似的强效抗病毒活性。3-epi 衍生物的活性是水飞蓟素的四倍。对 6'-hydroxy 基团和 C-5' 位置的修饰明显降低了其抗病毒活性。

  DOI：

  10.7164/antibiotics.55.165
• 作为产物：
  描述：

  (6AR,7S,9AS,13AS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3,11-dioxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以62%的产率得到(1S,13R,14S,17S,19R)-19-hydroxy-13,14,18,18-tetramethyl-10-phenylmethoxy-2-oxa-6-azapentacyclo[11.8.0.01,17.03,11.04,8]henicosa-3,8,10-trien-7-one
  参考文献：
  名称：

  Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260. II. Synthesis and Preliminary Structure-Activity Relationships of Stachyflin Derivatives.

  摘要：

  研究发现，由水苏芽孢杆菌 RF-7260 产生的水苏碱和乙酰水苏碱具有很强的抗甲型流感病毒活性。水飞蓟素是一类新型的甲型流感病毒血凝素融合抑制剂。研究人员从乙酰水飞蓟素合成了几种衍生物，并对它们的结构-活性关系进行了初步研究。其中，3-氧代和 3，8'-二氧代衍生物显示出与水飞蓟素相似的强效抗病毒活性。3-epi 衍生物的活性是水飞蓟素的四倍。对 6'-hydroxy 基团和 C-5' 位置的修饰明显降低了其抗病毒活性。

  DOI：

  10.7164/antibiotics.55.165

文献信息

• Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260. I. Isolation, Structure Elucidation and Biological Activities.
  作者：KAZUYUKI MINAGAWA、SHUICHI KOUZUKI、JUN YOSHIMOTO、YOSHIMI KAWAMURA、HIROYOSHI TANI、TATSUO IWATA、YOSHIHIRO TERUI、HIROSHI NAKAI、SHIGENORI YAGI、NAOHIKO HATTORI、TAMIO FUJIWARA、TOSHIYUKI KAMIGAUCHI

  DOI：10.7164/antibiotics.55.155

  日期：——

  Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003μM. Acetylstachyflin was about 77-fold less active than stachyflin.

  通过对RF-7260丝状酵母菌进行固态发酵，分离出两种新型化合物——丝状酵母菌素和乙酰丝状酵母菌素。通过详细的核磁共振分析和X射线晶体学分析，确定这两种代谢产物的结构是新颖的，具有包括顺式稠合萘在内的五环部分。通过圆二色性分析确定了丝状酵母菌素的绝对立体化学。丝状酵母菌素在体外对甲型流感病毒（H1N1）显示出抗病毒活性，IC50值为0.003μM。乙酰丝状酵母菌素的活性比丝状酵母菌素低约77倍。
• Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260. II. Synthesis and Preliminary Structure-Activity Relationships of Stachyflin Derivatives.
  作者：KAZUYUKI MINAGAWA、SHUICHI KOUZUKI、TOSHIYUKI KAMIGAUCHI

  DOI：10.7164/antibiotics.55.165

  日期：——

  Stachyflin and acetylstachyflin, produced by Stachybotrys sp. RF-7260, were found to have potent anti-influenza A virus activity. Stachyflin is a new class of hemagglutinin fusion inhibitors of influenza A virus. Several derivatives were synthesized from acetylstachyflin and subjected to preliminary examination of their structure-activity relationships. Among them, the 3-oxo and 3, 8'-dioxo derivatives showed potent antiviral activity similar to stachyflin. The 3-epi derivative was four times less active than stachyflin. Modification of the 6'-hydroxy group and the C-5' position markedly diminished the antiviral activity.

  研究发现，由水苏芽孢杆菌 RF-7260 产生的水苏碱和乙酰水苏碱具有很强的抗甲型流感病毒活性。水飞蓟素是一类新型的甲型流感病毒血凝素融合抑制剂。研究人员从乙酰水飞蓟素合成了几种衍生物，并对它们的结构-活性关系进行了初步研究。其中，3-氧代和 3，8'-二氧代衍生物显示出与水飞蓟素相似的强效抗病毒活性。3-epi 衍生物的活性是水飞蓟素的四倍。对 6'-hydroxy 基团和 C-5' 位置的修饰明显降低了其抗病毒活性。