12-hydroxy-N-(4-methoxy)benzoyldehydroabietylamine

• 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-hydroxy-N-(4-methoxy)benzoyldehydroabietylamine
• 英文别名: N-[[(1R,4aS,10aR)-6-hydroxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl]-4-methoxybenzamide
• 化学式: C₂₈H₃₇NO₃
• 分子量: 435.607
• InChiKey: AHYDIYAMTHCMPJ-RZDMPUFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-hydroxy-N-(4-methoxy)benzoyldehydroabietylamine 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到12-acetoxy-N-(4-methoxy)benzoyldehydroabietylamine
  参考文献：
  名称：

  Syntheses of C-ring modified dehydroabietylamides and their cytotoxic activity

  摘要：

  Due to their auspicious pharmacological efficacy as future drug candidates, natural products have been attracting scientific interest for centuries. An interesting field of research concerns the natural product class of terpenes. In this regard, a multitude of studies have already shown their promising biological potential. Therefore, a set of 27 derivatives of the diterpene dehydroabietylamine was synthesized, focusing on C-ring modifications and the derivatization of the amino moiety at C-18. Subsequent screening of the compounds in colorimetric sulforhodamine B-assays revealed an in vitro cytotoxicity especially towards malignant cell line MCF7. Particularly, 12-hydroxy-N-(isonicotinoyl)dehydroabietylamine and N-(4-methoxybenzoyl)dehydroabietylamine showed good cytotoxic activities (EC50 (MCF7) = 4.3 0.2 p,M and EC50 (MCF7) = 4.5 +/- 1.5 mu M, respectively) and significant selectivities (SI = 6.2 and SI = 8.8, respectively) towards malignant cell lines. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.051
• 作为产物：
  描述：

  (-)-N-phthaloyldehydroabietylamine 在 aluminum (III) chloride 、 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 12-hydroxy-N-(4-methoxy)benzoyldehydroabietylamine
  参考文献：
  名称：

  Syntheses of C-ring modified dehydroabietylamides and their cytotoxic activity

  摘要：

  Due to their auspicious pharmacological efficacy as future drug candidates, natural products have been attracting scientific interest for centuries. An interesting field of research concerns the natural product class of terpenes. In this regard, a multitude of studies have already shown their promising biological potential. Therefore, a set of 27 derivatives of the diterpene dehydroabietylamine was synthesized, focusing on C-ring modifications and the derivatization of the amino moiety at C-18. Subsequent screening of the compounds in colorimetric sulforhodamine B-assays revealed an in vitro cytotoxicity especially towards malignant cell line MCF7. Particularly, 12-hydroxy-N-(isonicotinoyl)dehydroabietylamine and N-(4-methoxybenzoyl)dehydroabietylamine showed good cytotoxic activities (EC50 (MCF7) = 4.3 0.2 p,M and EC50 (MCF7) = 4.5 +/- 1.5 mu M, respectively) and significant selectivities (SI = 6.2 and SI = 8.8, respectively) towards malignant cell lines. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.051

文献信息

• Syntheses of C-ring modified dehydroabietylamides and their cytotoxic activity
  作者：Jana Wiemann、Lucie Fischer、Matthias Rohmer、René Csuk

  DOI：10.1016/j.ejmech.2018.07.051

  日期：2018.8

  Due to their auspicious pharmacological efficacy as future drug candidates, natural products have been attracting scientific interest for centuries. An interesting field of research concerns the natural product class of terpenes. In this regard, a multitude of studies have already shown their promising biological potential. Therefore, a set of 27 derivatives of the diterpene dehydroabietylamine was synthesized, focusing on C-ring modifications and the derivatization of the amino moiety at C-18. Subsequent screening of the compounds in colorimetric sulforhodamine B-assays revealed an in vitro cytotoxicity especially towards malignant cell line MCF7. Particularly, 12-hydroxy-N-(isonicotinoyl)dehydroabietylamine and N-(4-methoxybenzoyl)dehydroabietylamine showed good cytotoxic activities (EC50 (MCF7) = 4.3 0.2 p,M and EC50 (MCF7) = 4.5 +/- 1.5 mu M, respectively) and significant selectivities (SI = 6.2 and SI = 8.8, respectively) towards malignant cell lines. (C) 2018 Elsevier Masson SAS. All rights reserved.