2-({[5-(2,6-dimethoxyphenyl)-1-(2-isopropyl-4-{[methyl(3-{methyl[6-(triisopropylsilyl)hex-5-yn-1-yl]amino}propyl)amino]carbonyl}phenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid | 1476064-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-({[5-(2,6-dimethoxyphenyl)-1-(2-isopropyl-4-{[methyl(3-{methyl[6-(triisopropylsilyl)hex-5-yn-1-yl]amino}propyl)amino]carbonyl}phenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid
• 英文别名: 2-[[5-(2,6-Dimethoxyphenyl)-1-[4-[methyl-[3-[methyl-[6-tri(propan-2-yl)silylhex-5-ynyl]amino]propyl]carbamoyl]-2-propan-2-ylphenyl]pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid；2-[[5-(2,6-dimethoxyphenyl)-1-[4-[methyl-[3-[methyl-[6-tri(propan-2-yl)silylhex-5-ynyl]amino]propyl]carbamoyl]-2-propan-2-ylphenyl]pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid
• CAS: 1476064-44-4
• 化学式: C₅₃H₇₇N₅O₆Si
• 分子量: 908.31
• InChiKey: MRZZJGQLXDULGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.47
• 重原子数：
  65
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-({[5-(2,6-dimethoxyphenyl)-1-(2-isopropyl-4-{[methyl(3-{methyl[6-(triisopropylsilyl)hex-5-yn-1-yl]amino}propyl)amino]carbonyl}phenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Evaluation of a ¹⁸F-Labeled Diarylpyrazole Glycoconjugate for the Imaging of NTS1-Positive Tumors

  摘要：

  Aiming to image NTS1 overexpressing tumors, the diarylpyrazole glycoconjugate 8, derived from the potent NTS1 antagonist SR142948A, was synthesized taking advantage of the palladium-catalyzed aminocarbonylation reaction. The glycoconjugate 8 displayed excellent affinity and selectivity toward NTS1. Radiosynthesis proceeded straightforwardly, obtaining [F-18]8 with excellent stability and highly beneficial biodistribution in vivo as demonstrated by PET imaging in HT29 tumor-bearing nude mice. Thus, the tracer [F-18]8 represents a highly promising candidate for PET imaging of NTS1-positive tumors.

  DOI：

  10.1021/jm401491e
• 作为产物：
  描述：

  6-氯己炔 在 正丁基锂 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium iodide 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 乙腈 为溶剂， 反应 96.5h， 生成 2-({[5-(2,6-dimethoxyphenyl)-1-(2-isopropyl-4-{[methyl(3-{methyl[6-(triisopropylsilyl)hex-5-yn-1-yl]amino}propyl)amino]carbonyl}phenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Evaluation of a ¹⁸F-Labeled Diarylpyrazole Glycoconjugate for the Imaging of NTS1-Positive Tumors

  摘要：

  Aiming to image NTS1 overexpressing tumors, the diarylpyrazole glycoconjugate 8, derived from the potent NTS1 antagonist SR142948A, was synthesized taking advantage of the palladium-catalyzed aminocarbonylation reaction. The glycoconjugate 8 displayed excellent affinity and selectivity toward NTS1. Radiosynthesis proceeded straightforwardly, obtaining [F-18]8 with excellent stability and highly beneficial biodistribution in vivo as demonstrated by PET imaging in HT29 tumor-bearing nude mice. Thus, the tracer [F-18]8 represents a highly promising candidate for PET imaging of NTS1-positive tumors.

  DOI：

  10.1021/jm401491e