5-benzoyl-4-phenyl-2-chloropyrimidine | 1414381-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoyl-4-phenyl-2-chloropyrimidine
• CAS: 1414381-82-0
• 化学式: C₁₇H₁₁ClN₂O
• 分子量: 294.74
• InChiKey: WDMWMPQOMWTNCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  5-benzoyl-4-phenyl-1H-pyrimidine-2(H)-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到5-benzoyl-4-phenyl-2-chloropyrimidine
  参考文献：
  名称：

  Structure of 5-benzoyl-4-phenyl-2-chloropyrimidine studied by X-ray diffraction, DFT calculations, NMR and FT-IR spectra

  摘要：

  In this work, 5-benzoyl-4-phenyl-2-chloropyrimidine (5B4P2CP) (C17H11ClN2O), was characterized by X-ray single crystal diffraction technique (XRD), IR-NMR spectroscopy and quantum chemical computational methods as both experimental and theoretically. The compound crystallizes in the orthorhombic space group P bca with Z = 8. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. The computed vibrational frequencies are used to determine the types of molecular motions associated with each of the experimental bands observed. From the optimized geometry of the molecule, vibrational frequencies, gauge-independent atomic orbital (GIAO) H-1 and C-13 NMR chemical shift values calculated for two basis sets. Also, molecular electrostatic potential (MEP) distribution, non-linear optical properties, frontier molecular orbitals (FMOs) and thermodynamic properties of the title compound were performed at B3LYP/6-311++G(d,p) level. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.07.010

文献信息

• Conjugation of Quinones with Natural Polyamines: Toward an Expanded Antitrypanosomatid Profile
  作者：Federica Lizzi、Giacomo Veronesi、Federica Belluti、Christian Bergamini、Almudena López-Sánchez、Marcel Kaiser、Reto Brun、R. Luise Krauth-Siegel、Dennis G. Hall、Luis Rivas、Maria Laura Bolognesi

  DOI：10.1021/jm301112z

  日期：2012.12.13

  A combinatorial library of quinone-polyamine conjugates designed to optimize the antitrypanosomatid profile of hit compounds 1 and 2 has been prepared by a solid-phase approach. The conjugates were evaluated against the three most important human trypanosomatid pathogens (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani), and several showed promising activity. A subset also inhibited trypanothione reductase in vitro and induced oxidase activity of the enzyme. A highly potent analogue (7) was identified with activity against T. brucei as low as 70 nM and a selectivity index of 72. Interestingly, the presence of a cadaverine tail confers to 7 the ability to target mitochondrial function in Leishmania. In fact, in L. donovani promastigotes, we verified for 7 a decrease of cytoplasmic ATP and mitochondrial potential. Therefore, the current results support the suitability of the conjugation approach for the development of novel polyamine conjugates with enhanced therapeutic potential.