(2R,5S)-1-Allyl-4-{(3-bromo-phenyl)-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methyl}-2,5-dimethyl-piperazine | 500912-24-3

• 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: (2R,5S)-1-Allyl-4-{(3-bromo-phenyl)-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methyl}-2,5-dimethyl-piperazine
• 英文别名: (2S,5R)-1-[(3-Bromophenyl)[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]methyl]-2,5-dimethyl-4-(2-propen-1-yl)piperazine；[3-[(3-bromophenyl)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]methyl]phenoxy]-tert-butyl-dimethylsilane
• CAS: 500912-24-3
• 化学式: C₂₈H₄₁BrN₂OSi
• 分子量: 529.636
• InChiKey: VEFARLKQITTZFK-OCTGXNKJSA-N

物化性质

• 沸点：
  516.2±50.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,5S)-1-Allyl-4-{(3-bromo-phenyl)-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methyl}-2,5-dimethyl-piperazine 在 咪唑 、 sodium hydroxide 、 草酰氯 、 四乙基氟化铵水合物 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium chloride 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 128.5h， 生成 DPI-3290
  参考文献：
  名称：

  3-(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)- N-alkyl-N-arylbenzamides:  Potent, Non-Peptidic Agonists of Both the μ and δ Opioid Receptors

  摘要：

  Opioid analgesics with both mu and delta opioid receptor activation represent a new approach to the treatment of severe pain with an improved safety profile. Compounds with this profile may exhibit strong analgesic properties due to mu agonism, with a reduced side effect profile resulting from delta agonism. Replacing the p-diethylamide of the known potent delta opioid receptor selective agonist BW373U86 with a m-diethylamide resulted in a compound with agonist activity at both the mu and delta opioid receptors. Modifying the amide to an N-methyl-N-phenylamide increased agonist potency at both receptors. A series of 3-(alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-alkyl-N-arylbenzamides have been made to explore the structure-activity relationship (SAR) around the N-methyl-N-phenylamide. Several potent agonists of both the mu and delta opioid receptors have been identified, including (+)-3-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-l-piperazinyl)-3-hydroxybenzyl)-N-(4-fluorophenyl)-N-methylben-zamide (23), which has EC50 values of 0.67 and 1.1 nM at the mu (guinea pig ileum assay) and delta (mouse vas deferens assay) opioid receptors, respectively.

  DOI：

  10.1021/jm020395s
• 作为产物：
  描述：

  α-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)-benzyl alcohol 在 氯化亚砜 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 (2R,5S)-1-Allyl-4-{(3-bromo-phenyl)-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methyl}-2,5-dimethyl-piperazine
  参考文献：
  名称：

  3-(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)- N-alkyl-N-arylbenzamides:  Potent, Non-Peptidic Agonists of Both the μ and δ Opioid Receptors

  摘要：

  Opioid analgesics with both mu and delta opioid receptor activation represent a new approach to the treatment of severe pain with an improved safety profile. Compounds with this profile may exhibit strong analgesic properties due to mu agonism, with a reduced side effect profile resulting from delta agonism. Replacing the p-diethylamide of the known potent delta opioid receptor selective agonist BW373U86 with a m-diethylamide resulted in a compound with agonist activity at both the mu and delta opioid receptors. Modifying the amide to an N-methyl-N-phenylamide increased agonist potency at both receptors. A series of 3-(alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-alkyl-N-arylbenzamides have been made to explore the structure-activity relationship (SAR) around the N-methyl-N-phenylamide. Several potent agonists of both the mu and delta opioid receptors have been identified, including (+)-3-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-l-piperazinyl)-3-hydroxybenzyl)-N-(4-fluorophenyl)-N-methylben-zamide (23), which has EC50 values of 0.67 and 1.1 nM at the mu (guinea pig ileum assay) and delta (mouse vas deferens assay) opioid receptors, respectively.

  DOI：

  10.1021/jm020395s