N-[3,5-bis(trifluoromethyl)benzyl]-N,2-dimethyl-4-phenylnicotinamide 1-oxide | 1303445-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[3,5-bis(trifluoromethyl)benzyl]-N,2-dimethyl-4-phenylnicotinamide 1-oxide
• 英文别名: VC1101；N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-N,2-dimethyl-1-oxido-4-phenylpyridin-1-ium-3-carboxamide
• CAS: 1303445-72-8
• 化学式: C₂₃H₁₈F₆N₂O₂
• 分子量: 468.399
• InChiKey: VOZXLKNXICFBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[3,5-bis(trifluoromethyl)benzyl]-N,2-dimethyl-4-phenylnicotinamide 1-oxide 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 N-[3,5-bis(trifluoromethyl)benzyl]-N,5-dimethyl-7-phenyl-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide
  参考文献：
  名称：

  Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety

  摘要：

  The quinoline nucleus of the previously described 4-phenylquinoline-3-carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole-(i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, respectively, in order to obtain NK1 receptor ligands showing lower molecular weight or higher hydrophilicity. The program of molecular manipulations produced NK1 receptor ligands showing affinity in the nanomolar range. In particular, 4-methyl-1-piperazinyl derivative 9j showed an IC50 value of 4.8 nM and was proved to behave as a NK1 antagonist blocking Sar(9)-SP-sulfone induced proliferation and migration of microvascular endothelial cells. Therefore, compound 9j has been labeled with [C-11]CH3I (t(1/2) = 20.4 min, beta(+) = 99.8%) starting from the corresponding des-methyl precursor 9i using with a radiochemical yield of about 10% (not decay corrected) and a specific radioactivity > 1 Ci/mu mol in order to be used as a radiotracer in next PET studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.031
• 作为产物：
  描述：

  2-methyl-4-phenylnicotinic acid 在 氯化亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 8.0h， 生成 N-[3,5-bis(trifluoromethyl)benzyl]-N,2-dimethyl-4-phenylnicotinamide 1-oxide
  参考文献：
  名称：

  Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety

  摘要：

  The quinoline nucleus of the previously described 4-phenylquinoline-3-carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole-(i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, respectively, in order to obtain NK1 receptor ligands showing lower molecular weight or higher hydrophilicity. The program of molecular manipulations produced NK1 receptor ligands showing affinity in the nanomolar range. In particular, 4-methyl-1-piperazinyl derivative 9j showed an IC50 value of 4.8 nM and was proved to behave as a NK1 antagonist blocking Sar(9)-SP-sulfone induced proliferation and migration of microvascular endothelial cells. Therefore, compound 9j has been labeled with [C-11]CH3I (t(1/2) = 20.4 min, beta(+) = 99.8%) starting from the corresponding des-methyl precursor 9i using with a radiochemical yield of about 10% (not decay corrected) and a specific radioactivity > 1 Ci/mu mol in order to be used as a radiotracer in next PET studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.031

文献信息

• Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety
  作者：Germano Giuliani、Andrea Cappelli、Mario Matarrese、Valeria Masiello、Elia Anna Turolla、Cristina Monterisi、Ferruccio Fazio、Maurizio Anzini、Gal.la Pericot Mohr、Daniela Riitano、Federica Finetti、Lucia Morbidelli、Marina Ziche、Gianluca Giorgi、Salvatore Vomero

  DOI：10.1016/j.bmc.2011.02.031

  日期：2011.4

  The quinoline nucleus of the previously described 4-phenylquinoline-3-carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole-(i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, respectively, in order to obtain NK1 receptor ligands showing lower molecular weight or higher hydrophilicity. The program of molecular manipulations produced NK1 receptor ligands showing affinity in the nanomolar range. In particular, 4-methyl-1-piperazinyl derivative 9j showed an IC50 value of 4.8 nM and was proved to behave as a NK1 antagonist blocking Sar(9)-SP-sulfone induced proliferation and migration of microvascular endothelial cells. Therefore, compound 9j has been labeled with [C-11]CH3I (t(1/2) = 20.4 min, beta(+) = 99.8%) starting from the corresponding des-methyl precursor 9i using with a radiochemical yield of about 10% (not decay corrected) and a specific radioactivity > 1 Ci/mu mol in order to be used as a radiotracer in next PET studies. (C) 2011 Elsevier Ltd. All rights reserved.