1-苯甲酰基-3-(2,3-二甲基苯基)硫脲 | 83697-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯甲酰基-3-(2,3-二甲基苯基)硫脲
• 英文名称: 1-benzoyl-3-(2,3-dimethylphenyl)thiourea
• 英文别名: N-[(2,3-dimethylphenyl)carbamothioyl]benzamide
• CAS: 83697-76-1
• 化学式: C₁₆H₁₆N₂OS
• 分子量: 284.382
• InChiKey: GMQCSFVUKKNJEV-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯甲酰基-3-(2,3-二甲基苯基)硫脲 在 sodium hydroxide 作用下， 反应 0.15h， 以95%的产率得到2,3-二甲基苯基硫脲
  参考文献：
  名称：

  Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

  摘要：

  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。

  DOI：

  10.1055/s-1988-27605
• 作为产物：
  描述：

  苯甲酰氯 以 乙酸乙酯 、 丙酮 为溶剂， 反应 3.0h， 生成 1-苯甲酰基-3-(2,3-二甲基苯基)硫脲
  参考文献：
  名称：

  Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against Klebsiella pneumoniae

  摘要：

  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。

  DOI：

  10.1039/c7md00354d

文献信息

• Structure–activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis
  作者：Anja Meissner、Helena I. Boshoff、Mahalakshmi Vasan、Benjamin P. Duckworth、Clifton E. Barry、Courtney C. Aldrich

  DOI：10.1016/j.bmc.2013.08.048

  日期：2013.11

  A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl)-1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 mu M or 0.008 mu g/mL in 7H9 media and therapeutic index of nearly similar to 300. However, 55 is rapidly metabolized by human liver microsomes (t(1/2) = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of similar to 10 (5). (C) 2013 Elsevier Ltd. All rights reserved.
• Optimization of 2-aminothiazole derivatives as CCR4 antagonists
  作者：Xuemei Wang、Feng Xu、Qingge Xu、Hossen Mahmud、Jonathan Houze、Liusheng Zhu、Michelle Akerman、George Tonn、Liang Tang、Brian E. McMaster、Daniel J. Dairaghi、Thomas J. Schall、Tassie L. Collins、Julio C. Medina

  DOI：10.1016/j.bmcl.2006.01.126

  日期：2006.5

  A series of 2-aminothiazole-derived antagonists of the CCR4 receptor has been synthesized and their affinity for the receptor evaluated using a [I-125]TARC (CCL17) displacement assay. Optimization of these compounds for potency and pharmacokinetic properties led to the discovery of potent, orally bioavailable antagonists. (C) 2006 Elsevier Ltd. All rights reserved.
• Solution-phase microwave assisted parallel synthesis of N,N′-disubstituted thioureas derived from benzoic acid: Biological evaluation and molecular docking studies
  作者：Muhammad Khawar Rauf、Ammara Talib、Amin Badshah、Sumera Zaib、Khurram Shoaib、Mohammad Shahid、Ulrich Flörke、Imtiaz-ud-Din、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2013.10.012

  日期：2013.12

  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.
• Upadhyaya Srivastava, Journal of the Indian Chemical Society, 1982, vol. 59, # 6, p. 767 - 768
  作者：Upadhyaya Srivastava

  DOI：——

  日期：——
• UPADHYAYA, J. S.;SRIVASTAVA, P. K., J. INDIAN CHEM. SOC., 1982, 59, N 6, 767-768
  作者：UPADHYAYA, J. S.、SRIVASTAVA, P. K.

  DOI：——

  日期：——