methyl (8R,9S,13S,14S,16S)-16-(8-aminooctyl)-13-methyl-17-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylate | 1220778-53-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl (8R,9S,13S,14S,16S)-16-(8-aminooctyl)-13-methyl-17-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylate
• CAS: 1220778-53-9
• 化学式: C₃₃H₄₉NO₅
• 分子量: 539.756
• InChiKey: DNYGBDZRBMVIBP-ZZNXQXLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  87.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (8R,9S,13S,14S,16S)-16-(8-aminooctyl)-13-methyl-17-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylate 、 苯丁酸氮芥 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (8R,9S,13S,14S,16S)-16-(8-(4-(4-(bis(2-chloroethyl)amino)phenyl)butanamido)octyl)-13-methyl-17-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of estradiol–chlorambucil hybrids as anticancer agents

  摘要：

  A series of estradiol-chlorambucil hybrids was synthesized as anticancer drugs for site-directed chemotherapy of breast cancer. The novel compounds were synthesized in good yields through efficient modifications of estrone at position 16 alpha of the steroid nucleus. The newly synthesized compounds were evaluated for their anticancer efficacy in different hormone-dependent and hormone-independent breast cancer cell lines. The novel hybrids showed significant in vitro anticancer activity when compared to chlorambucil. Structure-activity relationship (SAR) reveals the influence of the length of the spacer chain between carrier and drug molecule. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.053
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.17h， 生成 methyl (8R,9S,13S,14S,16S)-16-(8-aminooctyl)-13-methyl-17-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of estradiol–chlorambucil hybrids as anticancer agents

  摘要：

  A series of estradiol-chlorambucil hybrids was synthesized as anticancer drugs for site-directed chemotherapy of breast cancer. The novel compounds were synthesized in good yields through efficient modifications of estrone at position 16 alpha of the steroid nucleus. The newly synthesized compounds were evaluated for their anticancer efficacy in different hormone-dependent and hormone-independent breast cancer cell lines. The novel hybrids showed significant in vitro anticancer activity when compared to chlorambucil. Structure-activity relationship (SAR) reveals the influence of the length of the spacer chain between carrier and drug molecule. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.053