(2S,3R,5S,6S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-[5-(4-hydroxyphenyl)imidazol-1-yl]-6-methylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3,6-triol | 1221265-88-8

• 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: (2S,3R,5S,6S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-[5-(4-hydroxyphenyl)imidazol-1-yl]-6-methylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3,6-triol
• CAS: 1221265-88-8
• 化学式: C₃₆H₅₂N₂O₄
• 分子量: 576.82
• InChiKey: NPHOOYJQPTZJDL-JHGSQTGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  amaranzole A 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 以100%的产率得到(2S,3R,5S,6S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-[5-(4-hydroxyphenyl)imidazol-1-yl]-6-methylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3,6-triol
  参考文献：
  名称：

  Amaranzoles B−F, Imidazole-2-carboxy Steroids from the Marine Sponge Phorbas amaranthus. C24-N- and C24-O-Analogues from a Divergent Oxidative Biosynthesis

  摘要：

  Five new steroidal imidazoles, amaranzoles B-F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.

  DOI：

  10.1021/jo1000324