Tert-butyl 8-[tert-butyl(dimethyl)silyl]oxy-4-(trifluoromethylsulfonyloxy)spiro[chromene-2,4'-piperidine]-1'-carboxylate | 1013334-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Tert-butyl 8-[tert-butyl(dimethyl)silyl]oxy-4-(trifluoromethylsulfonyloxy)spiro[chromene-2,4'-piperidine]-1'-carboxylate
• CAS: 1013334-08-1
• 化学式: C₂₅H₃₆F₃NO₇SSi
• 分子量: 579.71
• InChiKey: AZSPUNKEWKVIFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Tert-butyl 8-[tert-butyl(dimethyl)silyl]oxy-4-(trifluoromethylsulfonyloxy)spiro[chromene-2,4'-piperidine]-1'-carboxylate 、 4-(N,N-二乙氨甲酰基)苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 4.0h， 生成 Tert-butyl 8-[tert-butyl(dimethyl)silyl]oxy-4-[4-(diethylcarbamoyl)phenyl]spiro[chromene-2,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Potent, Orally Bioavailable Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of N,N-Diethyl-4-(5-hydroxyspiro[chromene-2,4′-piperidine]-4-yl)benzamide (ADL5859)

  摘要：

  Selective 6 opioid receptor agonists are promising potential therapeutic agents for the treatment of various types of pain conditions. A spirocyclic derivative was identified as a promising hit through screening. Subsequent lead optimization identified compound 20 (ADL5859) as a potent, selective, and orally bioavailable 6 agonist. Compound 20 was selected as a clinical candidate for the treatment of pain.

  DOI：

  10.1021/jm8008986
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 tert-butyl 8-[tert-butyl(dimethyl)silyl]oxy-4-oxospiro[3H-chromene-2,4'-piperidine]-1'-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Tert-butyl 8-[tert-butyl(dimethyl)silyl]oxy-4-(trifluoromethylsulfonyloxy)spiro[chromene-2,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Potent, Orally Bioavailable Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of N,N-Diethyl-4-(5-hydroxyspiro[chromene-2,4′-piperidine]-4-yl)benzamide (ADL5859)

  摘要：

  Selective 6 opioid receptor agonists are promising potential therapeutic agents for the treatment of various types of pain conditions. A spirocyclic derivative was identified as a promising hit through screening. Subsequent lead optimization identified compound 20 (ADL5859) as a potent, selective, and orally bioavailable 6 agonist. Compound 20 was selected as a clinical candidate for the treatment of pain.

  DOI：

  10.1021/jm8008986

文献信息

• Potent, Orally Bioavailable Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of <i>N</i>,<i>N</i>-Diethyl-4-(5-hydroxyspiro[chromene-2,4′-piperidine]-4-yl)benzamide (ADL5859)
  作者：Bertrand Le Bourdonnec、Rolf T. Windh、Christopher W. Ajello、Lara K. Leister、Minghua Gu、Guo-Hua Chu、Paul A. Tuthill、William M. Barker、Michael Koblish、Daniel D. Wiant、Thomas M. Graczyk、Serge Belanger、Joel A. Cassel、Marina S. Feschenko、Bernice L. Brogdon、Steven A. Smith、David D. Christ、Michael J. Derelanko、Steve Kutz、Patrick J. Little、Robert N. DeHaven、Diane L. DeHaven-Hudkins、Roland E. Dolle

  DOI：10.1021/jm8008986

  日期：2008.10.9

  Selective 6 opioid receptor agonists are promising potential therapeutic agents for the treatment of various types of pain conditions. A spirocyclic derivative was identified as a promising hit through screening. Subsequent lead optimization identified compound 20 (ADL5859) as a potent, selective, and orally bioavailable 6 agonist. Compound 20 was selected as a clinical candidate for the treatment of pain.