5-萘-2-基-1H-吡唑-3-羧酸甲酯 | 164295-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-萘-2-基-1H-吡唑-3-羧酸甲酯
• 英文名称: 5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid methyl ester
• 英文别名: methyl 3-naphthalen-2-yl-1H-pyrazole-5-carboxylate
• CAS: 164295-93-6
• 化学式: C₁₅H₁₂N₂O₂
• mdl: MFCD06245485
• 分子量: 252.272
• InChiKey: YMLFDDSDTZENHS-UHFFFAOYSA-N

物化性质

• 沸点：
  495.9±33.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-萘-2-基-1H-吡唑-3-羧酸甲酯 在 sodium hydroxide 、 盐酸 作用下， 生成 5-萘-2-基-1H-吡唑-3-羧酸
  参考文献：
  名称：

  [EN] SPHINGOSINE KINASE INHIBITORS
  [FR] INHIBITEURS DE SPHINGOSINE KINASE

  摘要：

  公开号：

  WO2003105840A3
• 作为产物：
  描述：

  2-hydroxy-4-(2-naphthalenyl)-4-oxo-2-butenoic acid methyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 以14%的产率得到5-萘-2-基-1H-吡唑-3-羧酸甲酯
  参考文献：
  名称：

  Studies on New Acidic Azoles as Glucose-Lowering Agents in Obese, Diabetic db/db Mice

  摘要：

  Bioisosteric substitution was used as a tool to generate several new structural alternatives to the thiazolidine-2,4-dione and tetrazole heterocycles as potential antidiabetic agents. Among the initial leads that emerged from this strategy, a family of acidic azoles isoxazol-3- and -5-ones and a pyrazol-3-one, showed significant plasma glucose-lowering activity (17-42% reduction) in genetically obese, diabetic db/db mice at a dose of 100 mg/kg/day x 4. Structure-activity relationship studies determined that 5-alkyl-4-(arylmethyl)pyrazol-3-ones, which exist in solution as aromatic enol/iminol tautomers, were the most promising new class of potential antidiabetic agent (32-45% reduction at 20 mg/kg/d x 4). Included in this work are convenient syntheses for several types of acidic azoles that may find use as new acidic bioisosteres in medicinal chemistry such as the antidiabetic lead 5-(trifluoromethyl)pyrazol-3-one (hydroxy tautomer) and aza homologs of the pyrazolones, 1,2,3-triazol-5-ones (hydroxy tautomer) and 1,2,3,4-tetrazol-5-one heterocycles. log P and pK(a) data for 15 potential acidic bioisosteres, all appended to a 2-naphthalenylmethyl residue so as to maintain a similar distance between the acidic hydrogen and arene nucleus, are presented. This new data set allows comparison of a wide variety of potential acid mimetics (pK(a) 3.78-10.66; log P -0.21 to 2.76) for future drug design.

  DOI：

  10.1021/jm00004a008

文献信息

• Intramolecular Cyclization of Vinyldiazoacetates as a Versatile Route to Substituted Pyrazoles
  作者：Ivan Vilotijevic、Denis Drikermann、Valerie Kerndl、Helmar Görls

  DOI：10.1055/s-0040-1707111

  日期：2020.7

  Vinyldiazo compounds undergo a thermal electrocyclization to form pyrazoles in yields of up to 95%. The reactions are operationally simple, use readily available starting materials, require no intervention of a catalyst, and enable the synthesis of mono-, di- and tri-substituted pyrazoles. With the ability to produce highly substituted pyrazoles and the flexibility in installing various types of substituents

  乙烯基重氮化合物经过热电环化形成吡唑，产率高达 95%。该反应操作简单，使用容易获得的原料，不需要催化剂的干预，并且能够合成单、二和三取代的吡唑。由于能够生产高度取代的吡唑，并且可以灵活地安装各种类型的取代基，这种方法构成了这种有价值的杂环支架的新入口，可能对化学工业的所有分支感兴趣。
• SMALL MOLECULE MODULATORS OF HEPATOCYTE GROWTH FACTOR (SCATTER FACTOR) ACTIVITY
  申请人：Panicker Bijoy

  公开号：US20110237633A1

  公开（公告）日：2011-09-29

  The present invention provides compounds and pharmaceutically acceptable compositions thereof, and methods for the use thereof for the treatment of any of a number of conditions or diseases in which hepatocyte growth factor/scatter factor (HGF/SF) or the activities thereof, or agonists or antagonists thereof, have a therapeutically useful role.

  本发明提供化合物及其药学上可接受的组合物，以及使用它们治疗一系列疾病或病症的方法，其中包括肝细胞生长因子/散发因子（HGF/SF）或其活性，或其激动剂或拮抗剂在治疗中具有治疗作用。
• INTESTINAL ALKALINE PHOSPHATASE MODULATORS AND USES THEREOF
  申请人：Millan Jose Luis

  公开号：US20100016313A1

  公开（公告）日：2010-01-21

  Disclosed are modulators, i.e., activators and inhibitors, of Intestinal Alkaline Phosphatase (IAP). Also disclosed are methods for treating bacterial infections of the intestinal tract and methods for maintaining the health of the intestinal tract using IAP activators. Further disclosed are methods to assist in weight gain of emaciated patients and those having reduced or negligible fat absorption using IAP inhibitors.
• US7220764B2
  申请人：——

  公开号：US7220764B2

  公开（公告）日：2007-05-22
• [EN] SMALL MOLECULE MODULATORS OF HEPATOCYTE GROWTH FACTOR (SCATTER FACTOR) ACTIVITY<br/>[FR] MODULATEURS À PETITES MOLÉCULES DE L'ACTIVITÉ DU FACTEUR DE CROISSANCE (FACTEUR DE DISPERSION) DES HÉPATOCYTES
  申请人：ANGION BIOMEDICA CORP

  公开号：WO2010068287A2

  公开（公告）日：2010-06-17

  The present invention provides compounds and pharmaceutically acceptable compositions thereof, and methods for the use thereof for the treatment of any of a number of conditions or diseases in which hepatocyte growth factor/scatter factor (HGF/SF) or the activities thereof, or agonists or antagonists thereof, have a therapeutically useful role.