10β-cyano-3β-acetoxy-20-oxo-16α,17α-cyclohexano-19-norpregn-5-ene | 1122705-57-0

• 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: 10β-cyano-3β-acetoxy-20-oxo-16α,17α-cyclohexano-19-norpregn-5-ene
• CAS: 1122705-57-0
• 化学式: C₂₇H₃₇NO₃
• 分子量: 423.596
• InChiKey: CPTNCCSGIVDCQU-JEHALVDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  10β-cyano-3β-acetoxy-20-oxo-16α,17α-cyclohexano-19-norpregn-5-ene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以91%的产率得到10β-cyano-3β-hydroxy-20-oxo-16α,17α-cyclohexano-19-norpregn-5-ene
  参考文献：
  名称：

  3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: Synthesis and interactions with progesterone receptor and other proteins

  摘要：

  Series of 3- and 19-oximes of 16 alpha,17 alpha-cyclohexanoprogesterone derivatives (pregna-D'-pentaranes) have been synthesized with the aim of probing the surfaces of progesterone receptor's and two other protein ligand binding pockets neighboring to 3- and 19-positions of steroid core. The same derivatives were also studied as possible intermediates for attachment to matrixes. The data on affinity constants suggest the presence of hydrophobic cavities with hydrophilic necks in the progesterone receptor and serum pentaranophylin near C19 of bound ligand and the lack of such a cavity in uterine pentaranophylin. Any of 3-oxime substitutions were found to significantly diminish the ligand affinity for the progesterone receptor. It was also found that some of these modifications, in the Z-configuration particularly, might increase the affinity for serum and uterine pentaranophylins. The latter finding suggests the presence of large cavities near C3 of bound ligand in these proteins and interchangeability between 3-keto and 3-oxime groups in ligand-protein interactions. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.03.003
• 作为产物：
  描述：

  19(E/Z)-19-hydroxyimino-3β-hydroxy-20-oxo-16α,17α-cyclohexanopregn-5-ene 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以97%的产率得到10β-cyano-3β-acetoxy-20-oxo-16α,17α-cyclohexano-19-norpregn-5-ene
  参考文献：
  名称：

  3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: Synthesis and interactions with progesterone receptor and other proteins

  摘要：

  Series of 3- and 19-oximes of 16 alpha,17 alpha-cyclohexanoprogesterone derivatives (pregna-D'-pentaranes) have been synthesized with the aim of probing the surfaces of progesterone receptor's and two other protein ligand binding pockets neighboring to 3- and 19-positions of steroid core. The same derivatives were also studied as possible intermediates for attachment to matrixes. The data on affinity constants suggest the presence of hydrophobic cavities with hydrophilic necks in the progesterone receptor and serum pentaranophylin near C19 of bound ligand and the lack of such a cavity in uterine pentaranophylin. Any of 3-oxime substitutions were found to significantly diminish the ligand affinity for the progesterone receptor. It was also found that some of these modifications, in the Z-configuration particularly, might increase the affinity for serum and uterine pentaranophylins. The latter finding suggests the presence of large cavities near C3 of bound ligand in these proteins and interchangeability between 3-keto and 3-oxime groups in ligand-protein interactions. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.03.003