5-(4-chlorophenyl)-1-(6-methoxypyridazin-3-yl)-1H-pyrazole-3-carboxylic acid | 1443777-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-1-(6-methoxypyridazin-3-yl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 5-(4-Chlorophenyl)-1-(6-methoxypyridazin-3-yl)pyrazole-3-carboxylic acid；5-(4-chlorophenyl)-1-(6-methoxypyridazin-3-yl)pyrazole-3-carboxylic acid
• CAS: 1443777-68-1
• 化学式: C₁₅H₁₁ClN₄O₃
• 分子量: 330.73
• InChiKey: ZWKCWUNPZFSHKT-UHFFFAOYSA-N

物化性质

• 沸点：
  627.9±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-(6-methoxypyridazin-3-yl)-1H-pyrazole-3-carboxylic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-{[1-(6-methoxypyridazine-3-yl)-5-(4-chlorophenyl)-1H-pyrazole-3-yl]carbonyl}piperidine
  参考文献：
  名称：

  Pyrazole derivatives as inhibitors of arachidonic acid-induced platelet aggregation

  摘要：

  Antiplatelet drugs are promising therapeutics to intervene with platelet aggregation in arterial thrombosis, most prominently in myocardial infarction and ischemic stroke. Here, we describe the synthesis and structure activity relationships of potent inhibitors of platelet aggregation based on the 1,5-diarylpyrazol-3-carboxamide scaffold. Analogs from this series demonstrated potent anti-aggregatmy activities against arachidonic acid-induced platelet aggregation, as measured by turbidimetric method of Born. 1,5-Diarylpyrazole-3-carboxamides obtained with small-basic amines (7, 8, 50, 51, 61, 62) displayed the strongest activity with IC50 values in low nanomolar range (5.7-83 nM). On the basis of their high potency in cellular environment, these straightforward pyrazole derivatives may possess potential in the design of more potent compounds for intervention with cardiovascular diseases. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.048
• 作为产物：
  描述：

  对氯苯乙酮 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 7.5h， 生成 5-(4-chlorophenyl)-1-(6-methoxypyridazin-3-yl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Pyrazole derivatives as inhibitors of arachidonic acid-induced platelet aggregation

  摘要：

  Antiplatelet drugs are promising therapeutics to intervene with platelet aggregation in arterial thrombosis, most prominently in myocardial infarction and ischemic stroke. Here, we describe the synthesis and structure activity relationships of potent inhibitors of platelet aggregation based on the 1,5-diarylpyrazol-3-carboxamide scaffold. Analogs from this series demonstrated potent anti-aggregatmy activities against arachidonic acid-induced platelet aggregation, as measured by turbidimetric method of Born. 1,5-Diarylpyrazole-3-carboxamides obtained with small-basic amines (7, 8, 50, 51, 61, 62) displayed the strongest activity with IC50 values in low nanomolar range (5.7-83 nM). On the basis of their high potency in cellular environment, these straightforward pyrazole derivatives may possess potential in the design of more potent compounds for intervention with cardiovascular diseases. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.048

文献信息

• Crystal structure and DFT calculations of 5-(4-Chlorophenyl)-1-(6-methoxypyridazin-3-yl)-1H-pyrazole-3-carboxylic acid
  作者：Can Alaşalvar、Mustafa Serkan Soylu、Hüseyin Ünver、Nazan Ocak İskeleli、Mustafa Yildiz、Murat Çiftçi、Erden Banoğlu

  DOI：10.1016/j.saa.2014.05.014

  日期：2014.11

  The title compound, 5-(4-Chlorophenyl)-1-(6-methoxypyridazin-3-yl)-1H-pyrazole-3-carboxylic acid, has been characterized by using elemental analysis, MS, FT-IR, 1H NMR and 13C NMR spectroscopic, and crystallographic techniques. The title compound crystallizes in the triclinic space group P-1 with a=9.612(1), b=9.894(1), c=17.380(1)Å, α=90.213(5)°, β=104.99(1)°, γ=111.072(5)°, V=1481.3(2)Å3 and Dx=1.483 g cm(-3) respectively. The structure of the compound has also been examined by using quantum chemical methods. The molecular geometry and vibrational frequencies of monomeric and dimeric form of the title compound in the ground state have been calculated by using the B3LYP/6-31G(d,p) level of the theory. The calculated results show that the optimized geometry and the theoretical vibration frequencies of the dimeric form are good agreement with experimental data. In addition, HOMO-LUMO energy gap, molecular electrostatic potential map, thermodynamic properties of the title compound were performed at B3LYP/6-31G(d,p) level of theory.