(+)-N-(dodecanoyl)-dehydroabietylamine

• 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: (+)-N-(dodecanoyl)-dehydroabietylamine
• 英文别名: Sdccgsbi-0654281.P001；N-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl]dodecanamide
• 化学式: C₃₂H₅₃NO
• 分子量: 467.779
• InChiKey: ZJZPELRZWMRYGW-RUHGTMQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  月桂酰胺 、 氢化松香 在 borane tetrahydrofuran 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以93.15%的产率得到(+)-N-(dodecanoyl)-dehydroabietylamine
  参考文献：
  名称：

  Phenacyl group containing amide derivative of dehydroabietylamine exhibiting enhanced cytotoxic activity against PLC and MCF7 cancer cell lines

  摘要：

  New amide derivatives of (+)-dehydroabietylamine, tricyclic abietane diterpene amine, were prepared using Zhongping's protocol. (+)-N-(2-phenyl-acetyl)-dehydroabietylamine derivative (11) demonstrated noticeable growth attenuation of hepatocellular carcinoma cell lines including PLC/PRF/5, SNU475, Hep3B-TR, and Huh7 with IC50 of 7.4 A mu M, 9.8 A mu M, 11.7 A mu M, and 11.8 A mu M, respectively. A breast cancer cell line MCF7 was the most sensitive against amide 11 with lowest IC50 value (4.8 A mu M). Low cell confluence and increase in G2/M phase was recorded after 48 and 72 h of treatment of amide 11 on PLC/PRF/5 cell line. Finally, amide 11 has comparatively sufficient therapeutic role due to addition of N-phenacyl group at C-18. Amide 11 demonstrated as potential candidate for future cancer interference and research.

  DOI：

  10.1007/s00044-017-1859-0

文献信息

• Phenacyl group containing amide derivative of dehydroabietylamine exhibiting enhanced cytotoxic activity against PLC and MCF7 cancer cell lines
  作者：Muhammad Ayaz Mustufa、Afshan Aslam、Cigdem Ozen、Imran Ali Hashmi、Naim ul Hasan Naqvi、Mehmet Ozturk、Firdous Imran Ali

  DOI：10.1007/s00044-017-1859-0

  日期：2017.7

  New amide derivatives of (+)-dehydroabietylamine, tricyclic abietane diterpene amine, were prepared using Zhongping's protocol. (+)-N-(2-phenyl-acetyl)-dehydroabietylamine derivative (11) demonstrated noticeable growth attenuation of hepatocellular carcinoma cell lines including PLC/PRF/5, SNU475, Hep3B-TR, and Huh7 with IC50 of 7.4 A mu M, 9.8 A mu M, 11.7 A mu M, and 11.8 A mu M, respectively. A breast cancer cell line MCF7 was the most sensitive against amide 11 with lowest IC50 value (4.8 A mu M). Low cell confluence and increase in G2/M phase was recorded after 48 and 72 h of treatment of amide 11 on PLC/PRF/5 cell line. Finally, amide 11 has comparatively sufficient therapeutic role due to addition of N-phenacyl group at C-18. Amide 11 demonstrated as potential candidate for future cancer interference and research.