3'-methylaminoavarone | 83995-06-6

• 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: 3'-methylaminoavarone
• 英文别名: 2,5-Cyclohexadiene-1,4-dione, 2-(methylamino)-6-(((1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-；2-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-6-(methylamino)cyclohexa-2,5-diene-1,4-dione
• CAS: 83995-06-6
• 化学式: C₂₂H₃₁NO₂
• 分子量: 341.494
• InChiKey: LOWIFWWFLCSJQW-SFPRVHAESA-N

物化性质

• 熔点：
  152-155 °C(Solv: hexane (110-54-3))
• 沸点：
  447.3±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  阿瓦醇 在 hydroxide 、 silver(l) oxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 2.08h， 生成 3'-methylaminoavarone
  参考文献：
  名称：

  Potential Antipsoriatic Avarol Derivatives as Antioxidants and Inhibitors of PGE₂ Generation and Proliferation in the HaCaT Cell Line

  摘要：

  The synthesis and structure-activity relationships for a series of 14 new avarol derivatives as antioxidants and inhibitors of cell proliferation and PGE(2) generation in human keratinocytes are described. Compound 6 (thiosalicylic derivative) was the most potent inhibitor of superoxide generation in human neutrophils and also potently inhibited PGE(2) generation in the human keratinocyte HaCaT cell line. Compound 7 (3'-methylaminoavarone) presented the best antiproliferative profile, by the inhibition of H-3-thymidine incorporation in HaCaT cells, with potency similar to the reference compound anthralin. None of the avarol derivatives showed any sign of cytotoxicity measured as LDH release in treated keratinocytes. The potency and pharmacological profile of derivatives are also discussed.

  DOI：

  10.1021/np049873n

文献信息

• COZZOLINO, R.;DE, GIULIO A.;DE, ROSA S.;STRAZZULLO, G.;GASIC, M. J.;SLADI+, J. NATUR. PROD., 53,(1990) N, C. 699-702
  作者：COZZOLINO, R.、DE, GIULIO A.、DE, ROSA S.、STRAZZULLO, G.、GASIC, M. J.、SLADI+

  DOI：——

  日期：——
• Potential Antipsoriatic Avarol Derivatives as Antioxidants and Inhibitors of PGE₂ Generation and Proliferation in the HaCaT Cell Line
  作者：Maria Amigó、Maria Carmen Terencio、Maya Mitova、Carmine Iodice、Miguel Payá、Salvatore De Rosa

  DOI：10.1021/np049873n

  日期：2004.9.1

  The synthesis and structure-activity relationships for a series of 14 new avarol derivatives as antioxidants and inhibitors of cell proliferation and PGE(2) generation in human keratinocytes are described. Compound 6 (thiosalicylic derivative) was the most potent inhibitor of superoxide generation in human neutrophils and also potently inhibited PGE(2) generation in the human keratinocyte HaCaT cell line. Compound 7 (3'-methylaminoavarone) presented the best antiproliferative profile, by the inhibition of H-3-thymidine incorporation in HaCaT cells, with potency similar to the reference compound anthralin. None of the avarol derivatives showed any sign of cytotoxicity measured as LDH release in treated keratinocytes. The potency and pharmacological profile of derivatives are also discussed.