ethyl 1-(2-((2-(tert-butoxycarbonylamino)-ethyl)(4-ethoxy-4-oxobutyl)amino)ethyl)-1H-pyrazole-4-carboxylate | 1426251-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(2-((2-(tert-butoxycarbonylamino)-ethyl)(4-ethoxy-4-oxobutyl)amino)ethyl)-1H-pyrazole-4-carboxylate
• 英文别名: Ethyl 1-[2-[(4-ethoxy-4-oxobutyl)-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]ethyl]pyrazole-4-carboxylate
• CAS: 1426251-49-1
• 化学式: C₂₁H₃₆N₄O₆
• 分子量: 440.54
• InChiKey: WUAAZVJXPJHUMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2-((2-(tert-butoxycarbonylamino)-ethyl)(4-ethoxy-4-oxobutyl)amino)ethyl)-1H-pyrazole-4-carboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以29%的产率得到1-(2-((2-(tert-butoxycarbonylamino)ethyl)(3-carboxypropyl)amino)ethyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Influence of the Bifunctional Chelator on the Pharmacokinetic Properties of ^99mTc(CO)₃-Labeled Cyclic α-Melanocyte Stimulating Hormone Analog

  摘要：

  Aiming at the design of specific melanocortin-1 receptor (MC1R) targeted imaging probes, we report on the effect of different azolyl-ring substitution patterns (carboxylate at the 4-position and/or methyl groups at the 3,5 positions) of pyrazolyldiamine bifunctional chelators (Pz(2)-Pz(4)) on the pharmacokinetic profile of the Tc-99m(CO)(3)-labeled lactam bridge-cyclized alpha-melanocyte stimulating hormone derivative, beta AlaNleCycMSH(hex). Three pyrazolyl-diamine-containing chelators were conjugated to beta AlaNleCycMSH(hex), with the resulting peptide conjugates displaying subnanomolar MC1R binding affinity. Biodistribution studies in B16F1 melanoma-bearing mice show that all radiopeptides present a good melanoma uptake. The introduction of a carboxylate group in the azolyl-ring leads to a remarkable reduction of the kidney (>89%) and liver (>91%) accumulation for Tc-99m(CO)(3)-Pz(3)-beta AlaNleCycMSH(hex) and Tc-99m(CO)(3)-Pz(4)-beta AlaNleCycMSH(hex) when compared to the radiopeptide Tc-99m(CO)(3)-Pz(1)-beta AlaNleCycMSH(hex), where that group is absent. The good tumor uptake and favorable tumor-to-nontarget-organs ratios of Tc-99m(CO)(3)-Pz(3)-beta AlaNleCycMSH(hex) and Tc-99m(CO)(3)-Pz(4)-beta AlaNleCycMSH(hex) highlights the potential of both compounds as melanoma imaging agents.

  DOI：

  10.1021/jm301647t
• 作为产物：
  描述：

  4-溴丁酸乙酯 、 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以69%的产率得到ethyl 1-(2-((2-(tert-butoxycarbonylamino)-ethyl)(4-ethoxy-4-oxobutyl)amino)ethyl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Influence of the Bifunctional Chelator on the Pharmacokinetic Properties of ^99mTc(CO)₃-Labeled Cyclic α-Melanocyte Stimulating Hormone Analog

  摘要：

  Aiming at the design of specific melanocortin-1 receptor (MC1R) targeted imaging probes, we report on the effect of different azolyl-ring substitution patterns (carboxylate at the 4-position and/or methyl groups at the 3,5 positions) of pyrazolyldiamine bifunctional chelators (Pz(2)-Pz(4)) on the pharmacokinetic profile of the Tc-99m(CO)(3)-labeled lactam bridge-cyclized alpha-melanocyte stimulating hormone derivative, beta AlaNleCycMSH(hex). Three pyrazolyl-diamine-containing chelators were conjugated to beta AlaNleCycMSH(hex), with the resulting peptide conjugates displaying subnanomolar MC1R binding affinity. Biodistribution studies in B16F1 melanoma-bearing mice show that all radiopeptides present a good melanoma uptake. The introduction of a carboxylate group in the azolyl-ring leads to a remarkable reduction of the kidney (>89%) and liver (>91%) accumulation for Tc-99m(CO)(3)-Pz(3)-beta AlaNleCycMSH(hex) and Tc-99m(CO)(3)-Pz(4)-beta AlaNleCycMSH(hex) when compared to the radiopeptide Tc-99m(CO)(3)-Pz(1)-beta AlaNleCycMSH(hex), where that group is absent. The good tumor uptake and favorable tumor-to-nontarget-organs ratios of Tc-99m(CO)(3)-Pz(3)-beta AlaNleCycMSH(hex) and Tc-99m(CO)(3)-Pz(4)-beta AlaNleCycMSH(hex) highlights the potential of both compounds as melanoma imaging agents.

  DOI：

  10.1021/jm301647t