4'-benzylaminoavarone

• 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: 4'-benzylaminoavarone
• 英文别名: 2-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-5-(benzylamino)cyclohexa-2,5-diene-1,4-dione
• 化学式: C₂₈H₃₅NO₂
• 分子量: 417.591
• InChiKey: BWQCIYFHZMUGJG-XWARINQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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 碳酸氢钠 、 silver(l) oxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 2.08h， 生成 4'-benzylaminoavarone
  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

• Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential
  作者：Marko Jeremic、Jelena Dinic、Milica Pesic、Marija Stepanovic、Irena Novakovic、Dejan Segan、Dusan Sladic

  DOI：10.2298/jsc180627062j

  日期：——

  this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert -but­ylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/aryl­amino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cyto­toxic activity of the synthesized

  本文描述了倍半萜醌阿瓦隆及其模型化合物叔丁基醌的十四种烷基氨基和芳基氨基衍生物的合成。将支链的，环状的，烯丙基的和苄基的烷基氨基/芳基氨基基团引入醌部分。对于所有获得的衍生物，都对其生物活性和氧化还原性能进行了研究。研究了合成衍生物对多药耐药（MDR）人非小细胞肺癌NCI-H460 / R细胞，其敏感对应物NCI-H460和人正常角质形成细胞（HaCaT）的细胞毒活性。确定了对革兰氏阳性和革兰氏阴性细菌以及真菌培养物的抗菌活性。一些合成的衍生物显示出对包括MDR细胞在内的癌细胞的选择性。关于它们的细胞死亡诱导潜力，最有前途的化合物是烯丙基氨基衍生物，其优先触发凋亡，对包括MDR细胞在内的癌细胞具有高选择性。与商业抗生素和抗霉菌剂相比，几种化合物显示出令人鼓舞的抗菌活性。
• 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.