2-(3-Fluoro-naphthalen-2-yl)-5-methyl-2H-pyrazole-3-carboxylic acid (2'-sulfamoyl-biphenyl-4-yl)-amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-Fluoro-naphthalen-2-yl)-5-methyl-2H-pyrazole-3-carboxylic acid (2'-sulfamoyl-biphenyl-4-yl)-amide
• 英文别名: 2-(3-fluoronaphthalen-2-yl)-5-methyl-N-[4-(2-sulfamoylphenyl)phenyl]pyrazole-3-carboxamide
• 化学式: C₂₇H₂₁FN₄O₃S
• 分子量: 500.553
• InChiKey: STHFXJMXOVWINY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-fluoro-2-naphthoyl chloride 在 盐酸 、 sodium azide 、 三甲基铝 、 溶剂黄146 、 三氟乙酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 2-(3-Fluoro-naphthalen-2-yl)-5-methyl-2H-pyrazole-3-carboxylic acid (2'-sulfamoyl-biphenyl-4-yl)-amide
  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：Millennium Pharmaceuticals, Inc.

  公开号：US20040116399A1

  公开（公告）日：2004-06-17

  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.

  本发明揭示了一种具有对哺乳动物因子Xa活性的新化合物、其盐和相关组合物。这些化合物在体外或体内用于预防或治疗凝血障碍。
• 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
  作者：Zhaozhong J. Jia、Yanhong Wu、Wenrong Huang、Erick Goldman、Penglie Zhang、John Woolfrey、Paul Wong、Brian Huang、Uma Sinha、Gary Park、Andrea Reed、Robert M. Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00239-1

  日期：2002.6

  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.