(3-(4-hydroxyphenyl)-5-o-tolyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone | 1214751-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3-(4-hydroxyphenyl)-5-o-tolyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone
• 英文别名: [3-(4-hydroxyphenyl)-5-(o-tolyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone；(3-(4-Hydroxyphenyl)-5-o-tolyl-4,5-dihydro-1h-pyrazol-1-yl)(pyridin-3-yl)methanone；[5-(4-hydroxyphenyl)-3-(2-methylphenyl)-3,4-dihydropyrazol-2-yl]-pyridin-3-ylmethanone
• CAS: 1214751-10-6
• 化学式: C₂₂H₁₉N₃O₂
• 分子量: 357.412
• InChiKey: CAPQWYLERAGWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-吡啶甲酰肼 、 1-(4-hydroxyphenyl)-3-(o-tolyl)propenone 以 甲醇 为溶剂， 生成 (3-(4-hydroxyphenyl)-5-o-tolyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone
  参考文献：
  名称：

  Analysis of Intermolecular Interactions in 2,3,5 Trisubstituted Pyrazoles Derivatives: Insights into Crystal Structures, Gaussian B3LYP/6-311G (d,p), PIXELC and Hirshfeld Surface

  摘要：

  我们合成了吡唑的两种衍生物，其中一种在吡唑分子上连接的苯基环的正交位置进行了系统取代，并通过单晶 X 射线衍射进行了表征。分子的性质显示为平面，并对氢键特征进行了定量分析。这些衍生物在 B3LYP/6-311G (d,p) 下进行了几何优化和分子确认研究。利用 Hirshfeld 表面和二维指纹图定量研究了结构叠加、分子堆积和分子间氢键。在这两种化合物中，分子的堆积是通过强的 O-H--N和弱的 C-H--O、C-H--π 相互作用来稳定堆积的。此外，实验结构与几何优化结构之间的结构叠加以及量子化学水平的频率分析表明，中央吡唑分子和取代的苯基环存在偏差，其 RMSD 值分别为 0.5051 和 0.6305 Å。使用库仑-伦敦-保利（CLP）软件包中的 PIXELC 模块计算了这两种化合物的晶格能，并将其划分为相应的库仑贡献、极化贡献、色散贡献和排斥贡献。

  DOI：

  10.1007/s10870-016-0667-6

文献信息

• Synthesis and antimalarial evaluation of 1, 3, 5-trisubstituted pyrazolines
  作者：Badri Narayan Acharya、Deepika Saraswat、Mugdha Tiwari、Asish Kumar Shrivastava、Ramarao Ghorpade、Saroj Bapna、Mahabir Parshad Kaushik

  DOI：10.1016/j.ejmech.2009.10.023

  日期：2010.2

  A series of 1,3,5-trisubstituted pyrazolines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium falciparum. The activity was at nano molar concentration. beta-hematin formation inhibition activity (BHIA(50)) of the pyrazolines were determined and correlated with antimalarial activity. A reasonably good correlation (r = 0.62) was observed between antimalarial activity (IC50) and BHIA(50). This suggests that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. Some of the compounds were showing better antimalarial activity than chloroquine against resistant strain of P. falciparum and were also found active in the in vivo experiment. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Analysis of Intermolecular Interactions in 2,3,5 Trisubstituted Pyrazoles Derivatives: Insights into Crystal Structures, Gaussian B3LYP/6-311G (d,p), PIXELC and Hirshfeld Surface
  作者：Gayathri Purushothaman、Vijay Thiruvenkatam

  DOI：10.1007/s10870-016-0667-6

  日期：2016.9

  Two derivatives of pyrazole have been synthesized with one of the systematic substitutions made on the ortho position of the phenyl ring attached to the pyrazole moiety and characterised via single crystal X-ray diffraction. The nature of the molecules appear as planar with the hydrogen bonding features analysed quantitatively. The derivatives are geometrically optimized and studied for its molecular confirmation at the B3LYP/6-311G (d,p). The structure overlay, molecular packing and intermolecular hydrogen bonding are studied quantitatively using Hirshfeld surface and 2D fingerprint plots. In both the compounds, packing of the molecules is derived via strong O–H···N and weak C–H···O, C–H···π interactions stabilizing the packing. Further, the structure overlay between the experimental structures and the geometrically optimized structures along with frequency analysis at the quantum chemical level shows the deviation in the central pyrazole moiety and the substituted phenyl ring with the RMSD value of 0.5051 and 0.6305 Å respectively. The lattice energy is calculated for both the compounds using PIXELC module in Coulomb–London–Pauli (CLP) package and is partitioned into corresponding coulombic, polarization, dispersion and repulsion contributions.

  我们合成了吡唑的两种衍生物，其中一种在吡唑分子上连接的苯基环的正交位置进行了系统取代，并通过单晶 X 射线衍射进行了表征。分子的性质显示为平面，并对氢键特征进行了定量分析。这些衍生物在 B3LYP/6-311G (d,p) 下进行了几何优化和分子确认研究。利用 Hirshfeld 表面和二维指纹图定量研究了结构叠加、分子堆积和分子间氢键。在这两种化合物中，分子的堆积是通过强的 O-H--N和弱的 C-H--O、C-H--π 相互作用来稳定堆积的。此外，实验结构与几何优化结构之间的结构叠加以及量子化学水平的频率分析表明，中央吡唑分子和取代的苯基环存在偏差，其 RMSD 值分别为 0.5051 和 0.6305 Å。使用库仑-伦敦-保利（CLP）软件包中的 PIXELC 模块计算了这两种化合物的晶格能，并将其划分为相应的库仑贡献、极化贡献、色散贡献和排斥贡献。