5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one | 25652-49-7

• 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: 5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2-(1H)one；5-benzoyl-4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one；2-Oxo-5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidin；2-Oxo-5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydropyrimidine；5-benzoyl-4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 25652-49-7
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: KOBQZTXEIHUDQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 、 二苯甲酰基甲烷 、 尿素 在 protonated penta-6-hydroxypurine bismuth chloride cluster chlorine complex 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以80%的产率得到5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  （C5H6N4O）（C5H5N4O）3（C5H4N4O）[Bi2Cl11] Cl2作为Biginelli反应中的一种简单有效的催化剂

  摘要：

  开发了一种高效，简便的方法，该方法可通过醛，β-二羰基化合物和尿素/硫脲的一锅缩合反应一锅三组分合成3,4-二氢嘧啶-2-（1 H）酮/硫酮。该方法适用于（C 5 H 6 N 4 O）（C 5 H 5 N 4 O）3（C 5 H 4 N 4 O）[Bi 2 Cl 11 ] Cl 2。该络合物是一种对空气稳定，对环境友好且可回收的催化剂，可以有效催化Biginelli反应。该催化剂具有高催化效率和低催化剂载量，并且可以循环十次而活性损失很小。

  DOI：

  10.1002/aoc.3590

文献信息

• Revisit to the Biginelli reaction: a novel and recyclable bioglycerol-based sulfonic acid functionalized carbon catalyst for one-pot synthesis of substituted 3,4-dihydropyrimidin-2-(1H)-ones
  作者：Karnakar Konkala、Narayana Murthy Sabbavarapu、Ramesh Katla、Nageswar Yadavalli Venkata Durga、Vijai Kumar Reddy T、Prabhavathi Devi Bethala L.A.、Prasad Rachapudi B.N.

  DOI：10.1016/j.tetlet.2012.02.018

  日期：2012.4

  synthetic protocol has been developed for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by using a novel bioglycerol-based sulfonic acid functionalized carbon catalyst, devoid of moisture sensitive metal catalysts and corrosive acidic reagents. The developed method has the advantages of good to excellent yields, short reaction times, operational simplicity, and a recyclable catalyst. The catalyst can be

  通过使用新型的基于生物甘油的磺酸官能化的碳催化剂，开发了一种简单高效的合成方案，用于合成3,4-二氢嘧啶-2-（1 H）-一，该方法缺少对水分敏感的金属催化剂和腐蚀性酸性试剂。所开发的方法具有良好至优异的产率，短的反应时间，操作简单和可回收的催化剂的优点。该催化剂可以通过简单的方法由廉价且容易获得的甘油制备，并且已显示出可回收和可重复使用多达四个循环而没有任何活性损失。
• Structure based virtual screening-driven identification of monastrol as a potent urease inhibitor
  作者：Umer Rashid、Iram Batool、Abdul Wadood、Ajmal Khan、Zaheer ul-Haq、Muhammad Iqbal Chaudhary、Farzana Latif Ansari

  DOI：10.1016/j.jmgm.2013.04.006

  日期：2013.6

  Virtual screening uses computer based methods to discover new ligands on the basis of biological structures. Among all virtual screening methods structure based docking has received considerable attention. In an attempt to identify new ligands as urease inhibitors, structure-based virtual screening (SBVS) of an in-house database of 10,000 organic compounds was carried out. The X-ray crystallographic structure of Bacillus pasteurii (BP) in complex with acetohydroxamic acid (PDB Code 4UBP) was used as a protein structure. As a starting point, similar to 10,000 compounds of our in-house database were analyzed to check redundancy and the compounds found repeated were removed from the database. Finally 6993 compounds were docked into the active site of BP urease using GOLD and MOE-Dock software. A remarkable feature of this study was the identification of monastrol, a well-known KSP inhibitor already in clinical trials, as a novel urease inhibitor. The hits identified were further evaluated by molecular docking and on examination of the affinity predictions, twenty-seven analogs of monastrol were synthesized by a multicomponent Biginelli reaction followed by their in vitro screening as urease inhibitors. Finally twelve compounds were identified as new urease inhibitors. The excellent in vitro activity suggested that these compounds may serve as viable lead compounds for the treatment of urease related problems. (c) 2013 Elsevier Inc. All rights reserved.
• In vitro and in silico exploration of IL-2 inhibition by small drug-like molecules
  作者：Saima Kalsoom、Umer Rashid、Awais Shaukat、Omer Mohamed Abdalla、Khalida Hussain、Waqasuddin Khan、Samina Nazir、Mohammad Ahmad Mesaik、Zaheer-ul-Haq、Farzana Latif Ansari

  DOI：10.1007/s00044-013-0564-x

  日期：2013.12

  Interleukin-2 (IL-2) is an immunoregulatory cytokine produced by T lymphocytes in response to antigen. It is a potent growth and differentiation factor for several cell-types and is structurally related to the four-helix bundle family of cytokines. Here, we report IL-2 inhibitory potential and computational studies on different series of chalcones, benzothiazepines, semicarbazones, and dihydropyrimidines. These compounds were synthesized in wet lab and were then tested for their potency as IL-2 inhibitors through in vitro T cell proliferation, IL-2 cytokine production as well as their effect on oxidative burst. Compounds that showed significant suppressive activity were further evaluated for their cytotoxicity on normal two cell lines. Most of the chalcones were found to have a powerful inhibitory effect on T-lymphocytes proliferation and cytokine production. Among the aza heterocycles benzothiazepines, benzoxazepines, and benzodiazepinones were found to be the strongest IL-2 inhibitors. Molecular docking and MD simulation studies were carried out to correlate experimental and theoretical results whereby a good correlation was observed which indicated that computational studies could provide an alternate tool for the identification and designing of more potent IL-2 inhibitors.
• (C₅H₆N₄O)(C₅H₅N₄O)₃(C₅H₄N₄O)[Bi₂Cl₁₁]Cl₂as a simple and efficient catalyst in Biginelli reaction
  作者：Xiang Zhang、Xiaoyu Gu、Yuhua Gao、Shipeng Nie、Hongfei Lu

  DOI：10.1002/aoc.3590

  日期：2017.4

  A highly efficient and facile procedure for the one‐pot three‐component synthesis of 3,4‐dihydropyrimidin‐2‐(1H)ones/thiones from the one‐pot condensation of aldehyde, β‐dicarbonyl compound and urea/thiourea was developed. The methodology is applicable to a wide range of substrates with high yield in the presence of (C5H6N4O)(C5H5N4O)3(C5H4N4O)[Bi2Cl11]Cl2. The complex is an air‐stable, environmentally

  开发了一种高效，简便的方法，该方法可通过醛，β-二羰基化合物和尿素/硫脲的一锅缩合反应一锅三组分合成3,4-二氢嘧啶-2-（1 H）酮/硫酮。该方法适用于（C 5 H 6 N 4 O）（C 5 H 5 N 4 O）3（C 5 H 4 N 4 O）[Bi 2 Cl 11 ] Cl 2。该络合物是一种对空气稳定，对环境友好且可回收的催化剂，可以有效催化Biginelli反应。该催化剂具有高催化效率和低催化剂载量，并且可以循环十次而活性损失很小。