N-(pyrimidin-2-ylcarbamothioyl)benzamide | 31437-19-1

• 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: N-(pyrimidin-2-ylcarbamothioyl)benzamide
• 英文别名: 1-benzoyl-3-(pyrimidin-2-yl)thiourea；3-benzoyl-1-(pyrimidin-2-yl)thiourea；N-benzoyl-N'-(pyrimid-2-yl)-thiourea；N-benzoyl-N'-(2'-pyrimidyl)thiourea；benzoyl(2‐pyrimidyl)thiourea；1-benzoyl-3-pyrimidin-2-yl-thiourea
• CAS: 31437-19-1
• 化学式: C₁₂H₁₀N₄OS
• 分子量: 258.304
• InChiKey: UKAFILNIAQIJLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(pyrimidin-2-ylcarbamothioyl)benzamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.08h， 生成 (2-pyrimidyl)(2-thiazolyl)amine
  参考文献：
  名称：

  Kaplan, G. M.; Frolov, A. N.; El'tsov, A. V., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 1.2, p. 177 - 182

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-(pyrimidin-2-ylcarbamothioyl)benzamide
  参考文献：
  名称：

  Solution-phase microwave assisted parallel synthesis of N,N′-disubstituted thioureas derived from benzoic acid: Biological evaluation and molecular docking studies

  摘要：

  An efficient and facile microwave-assisted solution phase parallel synthesis for a 26-member library of N,N'-disubstituted thiourea analogs were accomplished successfully. The reaction time for synthesis of analogs was drastically reduced from a reported 8-12 h to only 10 min. Compounds were more than 95% pure, as characterized by modern analytical techniques, i.e. H-1 & C-13 NMR and FT-IR. The solid phase structural analysis has also been performed by single crystal XRD analysis. Synthesized compounds were preliminary screened for their in vitro urease inhibition and antifungal activity. Most of the compounds were found to be potent inhibitors of urease. However, the most significant activity was found for 11 with IC50 of 1.67 mu M. The docking scores correlate with the IC50 values of inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.012

文献信息

• Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas
  作者：C. R. Rasmussen、F. J. Villani, Jr.、L. E. Weaner、B. E. Reynolds、A. R. Hood、L. R. Hecker、S. O. Nortey、A. Hanslin、M. J. Costanzo、E. T. Powell、A. J. Molinari

  DOI：10.1055/s-1988-27605

  日期：——

  An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N′-benzoylthioureas with 5% aqueous sodium hydroxide. Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g., 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.

  制备芳基硫脲的改进方法包括将苯甲酰异硫氰酸酯与苯胺在丙酮中反应，然后用5%氢氧化钠水溶液对生成的N-芳基-N'-苯甲酰硫脲进行去苯甲酰化。双环烷基硫脲和N-(芳烷基)硫脲（例如9H-9-芴基硫脲）可直接由相应的异硫氰酸酯与氨反应制备。
• Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against <i>Klebsiella pneumoniae</i>
  作者：Rong Wang、Shuang Hou、Xiaojing Dong、Daijie Chen、Lei Shao、Liujia Qian、Zhong Li、Xiaoyong Xu

  DOI：10.1039/c7md00354d

  日期：——

  A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712).

  一系列融合的双环2-氨基噻唑基化合物被合成并评估其与多粘菌素B（PB）对抗肺炎克雷伯菌（SIPI-KPN-1712）的协同效应。
• Benzoylthioureas: Design, Synthesis and Antimycobacterial Evaluation
  作者：Tiago O. Brito、Lethícia O. Abreu、Karen M. Gomes、Maria C.S. Lourenço、Patricia M.L. Pereira、Sueli F. Yamada-Ogatta、Ângelo de Fàtima、Cesar A. Tisher、Fernando Macedo Jr、Marcelle L.F. Bispo

  DOI：10.2174/1573406415666181208110753

  日期：2020.1.16

  chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence

  背景技术迫切需要治疗结核病（TB）的新药物和策略。在这种情况下，硫脲衍生物具有广泛的生物活性，包括抗结核病。这个事实可以用一种古老的抗结核病药物异氧基的结构来说明，该结构具有硫脲作为药效基团。目的本研究的目的是描述59种苯甲酰硫脲衍生物的合成及其抗分枝杆菌活性。方法已合成苯甲酰硫脲衍生物，并使用MABA分析评估了其对结核分枝杆菌的活性。之后，已经对该系列化合物进行了结构-活性关系研究。结果与讨论19种化合物的抗分枝杆菌活性在423.1至9.6μM之间。一般来说，我们观察到，苯环对位的溴，氯和t-Bu基团的存在对A系列抗结核活性具有重要作用。这些取代基固定在苯环和其他基团（如Cl）上的该位置，Br，NO2和OMe引入苯甲酰基环中，从而生成B系列衍生物。通常，B系列的细胞毒性低于A系列，这表明在苯甲酰基环上存在取代基有助于两者的改进。抗分枝杆菌活性和毒性概况。结论化合物4c被认为是一个很好的原
• Pyrimidinone antibiotics—heterocyclic analogues with improved antibacterial spectrum
  作者：Michael Brands、Yolanda Cancho Grande、Rainer Endermann、Reinhold Gahlmann、Jochen Krüger、Siegfried Raddatz

  DOI：10.1016/s0960-894x(03)00578-x

  日期：2003.8

  We report the synthesis and pharmacological evaluation of new derivatives of the natural dipeptide antibiotic TAN 1057 A,B containing heterocycles either in the beta-amino acid side chain or as mimics of the urea function. In the course of this program, we identified novel analogues that display activity towards a broader panel of Gram-positive bacteriae.

  我们报告了天然二肽抗生素TAN 1057 A，B的新衍生物的合成和药理学评估，该衍生物在β-氨基酸侧链中或作为尿素功能的模拟物含有杂环。在该程序的过程中，我们确定了显示对更广泛的革兰氏阳性细菌具有活性的新型类似物。
• Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest
  作者：Tiago O. Brito、Aline X. Souza、Yane C. C. Mota、Vinicius S. S. Morais、Leandro T. de Souza、Ângelo de Fátima、Fernando Macedo、Luzia V. Modolo

  DOI：10.1039/c5ra07886e

  日期：——

  Urea is one of the most used nitrogen fertilizers worldwide.

  尿素是全球使用最广泛的氮肥之一。