deoxymicelianamide | 6901-87-7

• 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: deoxymicelianamide
• 英文别名: Desoxymycelianamid；Didesoxymycelianamid；3-[4-(3,7-dimethyl-octa-2,6-dienyloxy)-benzylidene]-6-methyl-piperazine-2,5-dione
• CAS: 6901-87-7；7315-53-9
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: WJYQOEOGXGQMEU-JVRIVONZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Boc-Ala-Gly-OMe 在 N-甲基吗啉 、 potassium tert-butylate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 仲丁醇 、 叔丁醇 为溶剂， 反应 19.0h， 生成 deoxymicelianamide
  参考文献：
  名称：

  Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines

  摘要：

  Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 mu M. A comparative study with the non-geranylated saturated derivative of (11) revealed the importance of the presence of the geranyloxy side chain and the exocyclic 2,5-DPK double bond moiety for the observed activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2014.07.010

文献信息

• Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines
  作者：Adriano Mollica、Roberto Costante、Serena Fiorito、Salvatore Genovese、Azzurra Stefanucci、Veronique Mathieu、Robert Kiss、Francesco Epifano

  DOI：10.1016/j.fitote.2014.07.010

  日期：2014.10

  Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 mu M. A comparative study with the non-geranylated saturated derivative of (11) revealed the importance of the presence of the geranyloxy side chain and the exocyclic 2,5-DPK double bond moiety for the observed activity. (C) 2014 Elsevier B.V. All rights reserved.