12-epi-scalaradial | 72300-72-2

• 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: 12-epi-scalaradial
• 英文别名: [(4aS,4bR,6R,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl] acetate
• CAS: 72300-72-2
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: ADWFEADZGIHPDE-VYGQJASISA-N

物化性质

• 沸点：
  505.3±50.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
• 稳定性/保质期：
  远离氧化物、光和热。

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-epi-scalaradial 、 盐酸甲胺 在 disodium hydrogenphosphate 作用下， 以 氘代乙腈 、 重水 为溶剂， 反应 0.08h， 生成 (5aS,5bR,7aS,11aS,11bR,13R,13aS,13bS)-13-Acetoxy-1-hydroxy-2,5b,8,8,11a,13a-hexamethyl-5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-hexadecahydro-1H-2-azonia-cyclopenta[a]chrysene; hydroxide 、 Acetic acid (4R,5aS,5bR,7aS,11aS,11bR,13R,13aS)-4-hydroxy-2,5b,8,8,11a,13a-hexamethyl-4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-hexadecahydro-2H-2-aza-cyclopenta[a]chrysen-13-yl ester
  参考文献：
  名称：

  Correlation of the reactivity of 1,4-dialdehydes with methylamine in biomimetic conditions to their hot taste: Covalent binding to primary amines as a molecular mechanism in hot taste receptors

  摘要：

  DOI：

  10.1016/s0040-4020(01)87721-8
• 作为产物：
  描述：

  12-deacetyl-12-epi-scalaradial 、 乙酸酐 在 吡啶 作用下， 生成 12-epi-scalaradial
  参考文献：
  名称：

  Scalarane Sesterterpenoids: Semisynthesis and Biological Activity

  摘要：

  Aiming to improve the potency and selectivity of scalarane sesterterpenoids, a series of natural and semisynthetic analogues, derived from the cytotoxic naturally abundant sesterterpene heteronemin (1), were evaluated for their in vitro antimicrobial and cytotoxic properties. The new sesterterpenes 16-O-methylsesterstatin 4 (6c), 17, 24-dihydroheteronemin (7a), 16, 25-deacetoxy-17, 24-dihydroheteronemin (7b), and 16-deacetoxy-25-methoxy-17, 24-dihydroheteronemin (7c) were structurally defined via physical data analyses. Scalarane sesterterpenes possessing an unsaturated 1,4-dialdehyde moiety showed potent inhibitory activity against methicillin-resistant Staphylococcus aureus at concentrations that are not significantly cytotoxic to mammalian cells. The structural features for the cytotoxicity of scalarane sesterterpenoids are discussed.

  DOI：

  10.1021/np900326a

文献信息

• Correlation of the reactivity of 1,4-dialdehydes with methylamine in biomimetic conditions to their hot taste: Covalent binding to primary amines as a molecular mechanism in hot taste receptors
  作者：G. Cimino、G. Sodano、A. Spinella

  DOI：10.1016/s0040-4020(01)87721-8

  日期：1987.1
• Scalarane Sesterterpenoids: Semisynthesis and Biological Activity
  作者：Haidy N. Kamel、Young B. Kim、John M. Rimoldi、Frank R. Fronczek、Daneel Ferreira、Marc Slattery

  DOI：10.1021/np900326a

  日期：2009.8.28

  Aiming to improve the potency and selectivity of scalarane sesterterpenoids, a series of natural and semisynthetic analogues, derived from the cytotoxic naturally abundant sesterterpene heteronemin (1), were evaluated for their in vitro antimicrobial and cytotoxic properties. The new sesterterpenes 16-O-methylsesterstatin 4 (6c), 17, 24-dihydroheteronemin (7a), 16, 25-deacetoxy-17, 24-dihydroheteronemin (7b), and 16-deacetoxy-25-methoxy-17, 24-dihydroheteronemin (7c) were structurally defined via physical data analyses. Scalarane sesterterpenes possessing an unsaturated 1,4-dialdehyde moiety showed potent inhibitory activity against methicillin-resistant Staphylococcus aureus at concentrations that are not significantly cytotoxic to mammalian cells. The structural features for the cytotoxicity of scalarane sesterterpenoids are discussed.