1-trityl-3,5-bis(ethoxymethyl)pyrazole | 1604807-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-trityl-3,5-bis(ethoxymethyl)pyrazole
• CAS: 1604807-73-9
• 化学式: C₂₈H₃₀N₂O₂
• 分子量: 426.558
• InChiKey: FUSJOGDGTOJIHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-trityl-3,5-bis(ethoxymethyl)pyrazole 在 盐酸 、 四丁基溴化铵 、 sodium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 丙酮 为溶剂， 反应 74.0h， 生成 tris[3,5-bis(ethoxymethyl)pyrazolyl]methane
  参考文献：
  名称：

  Re(I) and 99mTc(I) tricarbonyl complexes with ether-containing pyrazolyl-based chelators: Chemistry, biodistribution and metabolism

  摘要：

  Tris(pyrazolyl) methane chelators, L1-L3, containing one or two ether groups at different positions of the azole rings, were synthesized and fully characterized. These chelators enabled the synthesis of fac[Tc-99m(CO)(3){HC[4-(ROCH2) pz](3)}] _ (R = Me (Tc1), Et (Tc2)) and fac-[Tc-99m(CO)(3){HC[3,5-(EtOCH2)(2)pz](3)}](+) (Tc3) which were identified by HPLC in comparison with the rhenium counterparts. The evaluation of Tc1 -Tc3 in CD-1 mice has shown that the number and/ or nature of the ether groups greatly influence the biodistribution profile, pharmacokinetics and metabolic stability of these complexes. Tc1 and Tc2, bearing a unique ether substituent at the 4-position of the pyrazolyl ring, undergo metabolic transformation in vivo while Tc3 is not metabolized. The metabolization of Tc1 and Tc2 enhanced their rate of excretion but, most probably, also justify their negligible heart uptake in contrast with the high heart uptake of congener non-metabolizable complexes (Tc-99m-DMEOP and Tc-99m-TMEOP), which have recently emerged as potential myocardial imaging agents. The attempts made to identify the metabolites of Tc1 and Tc2 have shown that the metabolization of these compounds must involve the ether functions with probable formation of carboxylic acid derivatives. A comparative study with the congener fac-[Tc-99m(CO)(3){[4-(MeOCH2)pz](CH2)(2)NH(CH2)(2)NH2}](+) (Tc6) led us to confirm the formation of such type of metabolites. In fact, Tc6 is also metabolized in mice with formation of fac-[Tc-99m(CO)(3){[4-(HOCH2)pz](CH2)(2)NH(CH2)(2)NH2}](+) (Tc7) and fac-[Tc-99m(CO)(3){[4-(HOOC) pz](CH2)(2)NH(CH2)(2)NH2}](+) (Tc8), which were chemically identified by HPLC in comparison with the Re congeners (Re7 and Re8). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.11.013
• 作为产物：
  描述：

  碘乙烷 、 1-trityl-3,5-bis(hydroxymethyl)pyrazole 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.0h， 以96%的产率得到1-trityl-3,5-bis(ethoxymethyl)pyrazole
  参考文献：
  名称：

  Re(I) and 99mTc(I) tricarbonyl complexes with ether-containing pyrazolyl-based chelators: Chemistry, biodistribution and metabolism

  摘要：

  Tris(pyrazolyl) methane chelators, L1-L3, containing one or two ether groups at different positions of the azole rings, were synthesized and fully characterized. These chelators enabled the synthesis of fac[Tc-99m(CO)(3){HC[4-(ROCH2) pz](3)}] _ (R = Me (Tc1), Et (Tc2)) and fac-[Tc-99m(CO)(3){HC[3,5-(EtOCH2)(2)pz](3)}](+) (Tc3) which were identified by HPLC in comparison with the rhenium counterparts. The evaluation of Tc1 -Tc3 in CD-1 mice has shown that the number and/ or nature of the ether groups greatly influence the biodistribution profile, pharmacokinetics and metabolic stability of these complexes. Tc1 and Tc2, bearing a unique ether substituent at the 4-position of the pyrazolyl ring, undergo metabolic transformation in vivo while Tc3 is not metabolized. The metabolization of Tc1 and Tc2 enhanced their rate of excretion but, most probably, also justify their negligible heart uptake in contrast with the high heart uptake of congener non-metabolizable complexes (Tc-99m-DMEOP and Tc-99m-TMEOP), which have recently emerged as potential myocardial imaging agents. The attempts made to identify the metabolites of Tc1 and Tc2 have shown that the metabolization of these compounds must involve the ether functions with probable formation of carboxylic acid derivatives. A comparative study with the congener fac-[Tc-99m(CO)(3){[4-(MeOCH2)pz](CH2)(2)NH(CH2)(2)NH2}](+) (Tc6) led us to confirm the formation of such type of metabolites. In fact, Tc6 is also metabolized in mice with formation of fac-[Tc-99m(CO)(3){[4-(HOCH2)pz](CH2)(2)NH(CH2)(2)NH2}](+) (Tc7) and fac-[Tc-99m(CO)(3){[4-(HOOC) pz](CH2)(2)NH(CH2)(2)NH2}](+) (Tc8), which were chemically identified by HPLC in comparison with the Re congeners (Re7 and Re8). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.11.013