(5S,10R)-N-[3-(2-氨基-1H-咪唑-5-基)丙基]-7,9-二溴-10-羟基-8-甲氧基-1-氧杂-2-氮杂螺[4.5]癸-2,6,8-三烯-3-甲酰胺 | 87075-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (5S,10R)-N-[3-(2-氨基-1H-咪唑-5-基)丙基]-7,9-二溴-10-羟基-8-甲氧基-1-氧杂-2-氮杂螺[4.5]癸-2,6,8-三烯-3-甲酰胺
• 英文名称: (+)-aerophobin 2
• 英文别名: Aerophobin 2；(5S,6R)-N-[3-(2-amino-1H-imidazol-5-yl)propyl]-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
• CAS: 87075-23-8
• 化学式: C₁₆H₁₉Br₂N₅O₄
• 分子量: 505.166
• InChiKey: ZSZRBAQVYFYMTR-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,10R)-N-[3-(2-氨基-1H-咪唑-5-基)丙基]-7,9-二溴-10-羟基-8-甲氧基-1-氧杂-2-氮杂螺[4.5]癸-2,6,8-三烯-3-甲酰胺 在 咪唑 、 marine sponge Aplysina aerophoba 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 (1S,6R)-3,5-二溴-1,6-二羟基-4-甲氧基-2,4-环己二烯-1-乙腈
  参考文献：
  名称：

  Wound Activation of Protoxins in Marine Sponge Aplysina aerophoba

  摘要：

  The marine sponge Aplysina aerophoba accumulates brominated isoxazoline alkaloids, which include aerophobin-2, aplysinamisin-1, and isofistularin-3 as major constituents. Following disruption of compartmentalization, the isoxazoline alkaloids are enzymatically converted to aeroplysinin-1, which in rum gives rise to a dienone. The described bioconversions were demonstrated for the first time in vitro using an enzyme preparation from A. aerophoba. Cell-free extracts of other Aplysina species were capable of performing the same bioconversions, whereas enzyme extracts of sponges from other orders, which lack isoxazoline alkaloids, were inactive with regard to the reactions analyzed. These findings suggest that the enzyme activities studied are linked to the accumulation of suitable substrates and hence represent a specific biochemical property of sponges from the genus Aplysina. Time-course experiments with A. aerophoba, performed in situ, demonstrated that wound-induced bioconversions of isoxazoline alkaloids proceeded rapidly. Within 40 sec after mechanical damage of a tube of A. aerophoba, both aerophobin-2 and aplysinamisin-1 were completely converted to the dienone. The wound activation of protoxins results in a pronounced increase of the fish deterrent activity of A. aerophoba as shown in bioassays employing the common Caribbean wrasse Thalassoma bifasciatum.

  DOI：

  10.1023/b:joec.0000006475.10310.3a

文献信息

• Wound Activation of Protoxins in Marine Sponge Aplysina aerophoba
  作者：Rainer Ebel、Marko Brenzinger、Arno Kunze、Hans J. Gross、Peter Proksch

  DOI：10.1023/b:joec.0000006475.10310.3a

  日期：1997.5

  The marine sponge Aplysina aerophoba accumulates brominated isoxazoline alkaloids, which include aerophobin-2, aplysinamisin-1, and isofistularin-3 as major constituents. Following disruption of compartmentalization, the isoxazoline alkaloids are enzymatically converted to aeroplysinin-1, which in rum gives rise to a dienone. The described bioconversions were demonstrated for the first time in vitro using an enzyme preparation from A. aerophoba. Cell-free extracts of other Aplysina species were capable of performing the same bioconversions, whereas enzyme extracts of sponges from other orders, which lack isoxazoline alkaloids, were inactive with regard to the reactions analyzed. These findings suggest that the enzyme activities studied are linked to the accumulation of suitable substrates and hence represent a specific biochemical property of sponges from the genus Aplysina. Time-course experiments with A. aerophoba, performed in situ, demonstrated that wound-induced bioconversions of isoxazoline alkaloids proceeded rapidly. Within 40 sec after mechanical damage of a tube of A. aerophoba, both aerophobin-2 and aplysinamisin-1 were completely converted to the dienone. The wound activation of protoxins results in a pronounced increase of the fish deterrent activity of A. aerophoba as shown in bioassays employing the common Caribbean wrasse Thalassoma bifasciatum.