(S)-DPP-0113 | 905952-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-DPP-0113
• 英文别名: 1-[4-[3-[4-[[(2S)-2,3-dihydroxypropyl]amino]-3-methylphenyl]pentan-3-yl]-2-methylphenoxy]-3,3-dimethylbutan-2-one
• CAS: 905952-05-8
• 化学式: C₂₈H₄₁NO₄
• 分子量: 455.638
• InChiKey: YUHGPRDTZYLKEH-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-DPP-0113 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R,S)-DPP-0123 、 (S,S)-DPP-0123
  参考文献：
  名称：

  Ligands with a 3,3-diphenylpentane skeleton for nuclear vitamin D and androgen receptors: Dual activities and metabolic activation

  摘要：

  Ligands possessing dual vitamin D-3 (VD3)-agonistic and androgen-antagonistic activities with various activity spectra were prepared based on a substituted 3,3-diphenylpentane (DPP) skeleton. Among the compounds, (R,S)-DPP-1023 [(R,S)-7b] and (S,S)-DPP-0123 [(S,S)-7c] showed the most potent vitamin D-3-agonistic activity [with potency comparable to that of 1 alpha,25-dihydroxyvitamin D-3 (1,25-VD3)] and nuclear androgen receptor (AR)-binding activity (with higher affinity than that of hydroxyflutamide), respectively. Metabolic activation (reduction of the carbonyl group) of pivaloyl analogs [DPP- 1113 (3a), DPP- 10 13 (3b), DPP-0113 (3c), and DPP-0013 (3d)] in HL-60 cells was found to be necessary for binding to nuclear vitamin D-3 receptor (VDR). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.039
• 作为产物：
  描述：

  一氯频呐酮 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 (S)-DPP-0113
  参考文献：
  名称：

  Ligands with a 3,3-diphenylpentane skeleton for nuclear vitamin D and androgen receptors: Dual activities and metabolic activation

  摘要：

  Ligands possessing dual vitamin D-3 (VD3)-agonistic and androgen-antagonistic activities with various activity spectra were prepared based on a substituted 3,3-diphenylpentane (DPP) skeleton. Among the compounds, (R,S)-DPP-1023 [(R,S)-7b] and (S,S)-DPP-0123 [(S,S)-7c] showed the most potent vitamin D-3-agonistic activity [with potency comparable to that of 1 alpha,25-dihydroxyvitamin D-3 (1,25-VD3)] and nuclear androgen receptor (AR)-binding activity (with higher affinity than that of hydroxyflutamide), respectively. Metabolic activation (reduction of the carbonyl group) of pivaloyl analogs [DPP- 1113 (3a), DPP- 10 13 (3b), DPP-0113 (3c), and DPP-0013 (3d)] in HL-60 cells was found to be necessary for binding to nuclear vitamin D-3 receptor (VDR). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.039

文献信息

• Ligands with a 3,3-diphenylpentane skeleton for nuclear vitamin D and androgen receptors: Dual activities and metabolic activation
  作者：Shinnosuke Hosoda、Aya Tanatani、Ken-ichi Wakabayashi、Makoto Makishima、Keisuke Imai、Hiroyuki Miyachi、Kazuo Nagasawa、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2006.04.039

  日期：2006.8

  Ligands possessing dual vitamin D-3 (VD3)-agonistic and androgen-antagonistic activities with various activity spectra were prepared based on a substituted 3,3-diphenylpentane (DPP) skeleton. Among the compounds, (R,S)-DPP-1023 [(R,S)-7b] and (S,S)-DPP-0123 [(S,S)-7c] showed the most potent vitamin D-3-agonistic activity [with potency comparable to that of 1 alpha,25-dihydroxyvitamin D-3 (1,25-VD3)] and nuclear androgen receptor (AR)-binding activity (with higher affinity than that of hydroxyflutamide), respectively. Metabolic activation (reduction of the carbonyl group) of pivaloyl analogs [DPP- 1113 (3a), DPP- 10 13 (3b), DPP-0113 (3c), and DPP-0013 (3d)] in HL-60 cells was found to be necessary for binding to nuclear vitamin D-3 receptor (VDR). (c) 2006 Elsevier Ltd. All rights reserved.