(+)-cacospongionolide E

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-cacospongionolide E
• 英文别名: 3-[(2R)-5-[2-[(1S,2S,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-3,6-dihydro-2H-pyran-2-yl]-2-hydroxy-2H-furan-5-one
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: WBDQPITVPUAHAN-UEJZYZGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (+)-cacospongionolide E 在 吡啶 作用下， 反应 2.0h， 以1.5 mg的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-5-oxo-3-{(R)-5-[2-((1S,2S,4aR,8aR)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2,5-dihydro-furan-2-yl ester
  参考文献：
  名称：

  A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A₂ from the Tyrrhenian Sponge Fasciospongia cavernosa and Absolute Configuration of Cacospongionolides

  摘要：

  A new inhibitor of human secretory phospholipase A(2) (PLA(2)), cacospongionolide E (4a), has been isolated from the Tyrrhenian sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and by chemical transformations. The absolute configuration of cacospongionolides 2a-4a was established using the modified Mosher's method. Cacospongionolide E was the most potent inhibitor toward human synovial PLA(2), showing higher potency than the reference compound manoalide and exerting no signs of toxicity on human neutrophils. It showed high activity in the Artemia salina bioassay and moderate toxicity in the fish (Gambusia affinis) lethality assay.

  DOI：

  10.1021/np980122t
• 作为产物：
  描述：

  3-糠醛 在 rhodium(III) chloride 、 Grubbs catalyst first generation 、 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 氨 、 氢气 、 氧气 、 lithium 、 rose bengal 、 sodium hydride 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 为溶剂， -78.0~75.0 ℃ 、303.98 kPa 条件下， 反应 358.0h， 生成 (+)-cacospongionolide E
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e

文献信息

• Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition
  作者：Atwood K. Cheung、Ryan Murelli、Marc L. Snapper

  DOI：10.1021/jo049285e

  日期：2004.8.1

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.
• A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A₂ from the Tyrrhenian Sponge <i>Fasciospongia cavernosa </i>and Absolute Configuration of Cacospongionolides
  作者：Salvatore De Rosa、Antonio Crispino、Alfonso De Giulio、Carmine Iodice、Rachid Benrezzouk、M. Carmen Terencio、M. Luisa Ferrándiz、M. José Alcaraz、Miguel Payá

  DOI：10.1021/np980122t

  日期：1998.7.1

  A new inhibitor of human secretory phospholipase A(2) (PLA(2)), cacospongionolide E (4a), has been isolated from the Tyrrhenian sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and by chemical transformations. The absolute configuration of cacospongionolides 2a-4a was established using the modified Mosher's method. Cacospongionolide E was the most potent inhibitor toward human synovial PLA(2), showing higher potency than the reference compound manoalide and exerting no signs of toxicity on human neutrophils. It showed high activity in the Artemia salina bioassay and moderate toxicity in the fish (Gambusia affinis) lethality assay.