ethyl 1-(6-chloro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate | 479499-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-(6-chloro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate
• CAS: 479499-84-8
• 化学式: C₁₇H₁₅ClN₂O₂
• 分子量: 314.771
• InChiKey: OJPIEBBCEDBWPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-(6-chloro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate 在 硫化氢 、 三甲基铝 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 生成 2-(6-chloronaphthalen-2-yl)-N-[2-fluoro-4-(piperidine-1-carboximidoyl)phenyl]-5-methylpyrazole-3-carboxamide
  参考文献：
  名称：

  1-(2-Naphthyl)-1 H -pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 3: Design, synthesis and SAR of orally bioavailable benzamidine-P4 inhibitors

  摘要：

  Using N,N-dialkylated benzamidines as the novel P4 motifs, we have designed and synthesized a class of 1-(2-naphthyl)-1H-pyrazole-5-carboxylamides as highly potent and selective fXa inhibitors with significantly improved hydrophilicity and in vitro anticoagulant activity. These benzamidine-P4 fXa inhibitors have displayed excellent oral bioavailability and long half-life. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.054
• 作为产物：
  描述：

  ethyl 3-methyl-1-(6-bromo-2-naphthyl)-1H-pyrazole-5-carboxylate 在 copper(l) iodide 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 ethyl 1-(6-chloro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological activity of novel non-amidine factor Xa inhibitors. Part 1: P1 structure–activity relationships of the substituted 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides

  摘要：

  Based on DuPont Pharmaceuticals' monobenzamidine lead structure SN429, we have designed the biphenyl 1-(2-naphthyl)-1H-pyrazole-5-carboxylamides as a novel series of non-basic factor Xa inhibitors. We have discovered that the displacement of the benzamidine moiety with substituted 2-naphthyl structures not only results in highly potent factor Xa inhibitors, but also significantly increases their enzyme specificity and oral bioavailability. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00239-1