ethyl 1-(3-fluoro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate | 330803-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-(3-fluoro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 3-methyl-1-(3-fluoro-2-naphthyl)-1H-pyrazole-5-carboxylate；ethyl 2-(3-fluoronaphthalen-2-yl)-5-methylpyrazole-3-carboxylate
• CAS: 330803-46-8
• 化学式: C₁₇H₁₅FN₂O₂
• 分子量: 298.317
• InChiKey: FNXHXGQABFRXPC-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(3-fluoro-2-naphthyl)-3-methyl-1H-pyrazole-5-carboxylate 在 硫化氢 、 三甲基铝 、 三乙胺 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 生成 3-Fluoro-4-{[2-(3-fluoro-naphthalen-2-yl)-5-methyl-2H-pyrazole-3-carbonyl]-amino}-thiobenzimidic acid methyl ester
  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：

  3-fluoro-2-naphthoyl chloride 在 盐酸 、 sodium azide 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 10.5h， 生成 ethyl 1-(3-fluoro-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

文献信息

• Inhibitors of factor Xa
  申请人：——

  公开号：US20020091116A1

  公开（公告）日：2002-07-11

  Novel compounds, their salts and compositions related thereto having activity against mammalian factor Xa are disclosed. The compounds are useful in vitro or in vivo for preventing or treating coagulation disorders.

  揭示了针对哺乳动物因子Xa具有活性的新化合物、它们的盐和相关组合物。这些化合物在体外或体内用于预防或治疗凝血障碍。
• INHIBITORS OF FACTOR Xa
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：EP1216231A2

  公开（公告）日：2002-06-26
• US6632815B2
  申请人：——

  公开号：US6632815B2

  公开（公告）日：2003-10-14
• US6686368B1
  申请人：——

  公开号：US6686368B1

  公开（公告）日：2004-02-03
• US6720317B1
  申请人：——

  公开号：US6720317B1

  公开（公告）日：2004-04-13