2-hydroxy-6E-hydroximinocholesta-1,4-dien-3-one | 360067-77-2

• 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: 2-hydroxy-6E-hydroximinocholesta-1,4-dien-3-one
• 英文别名: (6E,8S,9S,10S,13R,14S,17R)-2-hydroxy-6-hydroxyimino-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-3-one
• CAS: 360067-77-2
• 化学式: C₂₇H₄₁NO₃
• 分子量: 427.627
• InChiKey: AGHDZMKTPDANEA-HBEGYKGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2α,3α-dihydroxy-6E-hydroximinocholest-4-ene 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 17.0h， 以50%的产率得到2-hydroxy-6E-hydroximinocholesta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n

文献信息

• Synthesis of Cytotoxic 6<i>E</i>-Hydroximino-4-ene Steroids:  Structure/Activity Studies
  作者：Noé Deive、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1021/jm010867n

  日期：2001.8.1

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.