N-(6-Amino-hexyl)-2-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylideneaminooxy]-acetamide | 952702-54-4

• 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: N-(6-Amino-hexyl)-2-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylideneaminooxy]-acetamide
• CAS: 952702-54-4
• 化学式: C₂₆H₃₉N₃O₃
• 分子量: 441.614
• InChiKey: BWJDXXARTYKABU-WHNBBEOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  96.94
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  生物素化-epsilon-氨基己酸-N-羟基丁二酰亚胺活化酯 、 N-(6-Amino-hexyl)-2-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylideneaminooxy]-acetamide 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-{6-[[({[3-hydroxyestra-1(10),2,4-trien-17-ylidene]amino}oxy)acetyl]amino]hexyl}-6-{[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]amino}hexanamide
  参考文献：
  名称：

  Facile Synthesis of CIDs:  Biotinylated Estrone Oximes Efficiently Heterodimerize Estrogen Receptor and Streptavidin Proteins in Yeast Three Hybrid Systems

  摘要：

  We synthesized estrone oximes as chemical inducers of protein heterodimerization (CIDs). Estrone-17-(O-carboxymethyl)oxime coupled to biotinamidocaproic acid via N,N'-dimethylhexane-1,6-diamine efficiently heterodimerizes estrogen receptors (ERs) and streptavidin Y43A in yeast three hybrid systems, activating gene expression over 100-fold at 10 muM. Related hexane-1,6-diamine and estradiol-6-(O-carboxymethyl)oxime derivatives were ineffective CIDs due to low affinity for ERs when bound to streptavidin. Estrone oximes bind ERs with submicromolar affinity and effectively display small molecules to target proteins expressed in yeast.

  DOI：

  10.1021/ol0497537
• 作为产物：
  描述：

  ({[3-hydroxyestra-1(10),2,4-trien-17-ylidene]amino}oxy)acetic acid 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(6-Amino-hexyl)-2-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylideneaminooxy]-acetamide
  参考文献：
  名称：

  Facile Synthesis of CIDs:  Biotinylated Estrone Oximes Efficiently Heterodimerize Estrogen Receptor and Streptavidin Proteins in Yeast Three Hybrid Systems

  摘要：

  We synthesized estrone oximes as chemical inducers of protein heterodimerization (CIDs). Estrone-17-(O-carboxymethyl)oxime coupled to biotinamidocaproic acid via N,N'-dimethylhexane-1,6-diamine efficiently heterodimerizes estrogen receptors (ERs) and streptavidin Y43A in yeast three hybrid systems, activating gene expression over 100-fold at 10 muM. Related hexane-1,6-diamine and estradiol-6-(O-carboxymethyl)oxime derivatives were ineffective CIDs due to low affinity for ERs when bound to streptavidin. Estrone oximes bind ERs with submicromolar affinity and effectively display small molecules to target proteins expressed in yeast.

  DOI：

  10.1021/ol0497537