N-(2,5-dimethoxyphenyl)-N'-benzoylthiocarbamide | 67617-97-4

• 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-(2,5-dimethoxyphenyl)-N'-benzoylthiocarbamide
• 英文别名: 1-(2,5-Dimethoxyphenyl)-3-benzoylthioharnstoff；N-[(2,5-dimethoxyphenyl)carbamothioyl]benzamide
• CAS: 67617-97-4
• 化学式: C₁₆H₁₆N₂O₃S
• 分子量: 316.381
• InChiKey: RQLQKROEEJIYGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,5-dimethoxyphenyl)-N'-benzoylthiocarbamide 在 sodium hydroxide 作用下， 生成 2,5-二甲氧苯基硫脲
  参考文献：
  名称：

  取代，芳基苯基噻唑基苯基羧酰胺作为潜在的蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂的合成，合成孔径雷达和对接研究。

  摘要：

  在我们不断努力发现具有改善的体内活性的新型PTP1B抑制剂的过程中，我们尝试通过用苯甲酰基取代磺酰基以产生化合物II来优化我们先前发现的先导化合物。对化合物II进行了其他结构修饰，以产生一系列24种芳基苯基噻唑基苯基羧酰胺，作为潜在的PTP1B抑制剂。在测试的24种化合物中，有6种化合物显示出良好的PTP1B抑制活性，而化合物38是最有前途的化合物。化合物38的合理的PTP1B结合位点相互作用显示出与已知PTP1B结合剂相似的有利结合，表明了其对PTP1B的选择性。化合物38还显示出在STZ模型和db / db小鼠模型中体内有希望的抗高血糖，抗血脂异常和胰岛素抵抗的逆转活性。总之，化合物38为未来以PTP1B为靶标的药物发现提供了极好的候选者。

  DOI：

  10.1111/cbdd.13515
• 作为产物：
  描述：

  苯甲酰基异硫氰酸酯 、 2,5-二甲氧基苯胺 以 苯 为溶剂， 反应 2.0h， 生成 N-(2,5-dimethoxyphenyl)-N'-benzoylthiocarbamide
  参考文献：
  名称：

  取代的芳基噻唑基苯磺酰胺作为潜在的蛋白质酪氨酸磷酸酶1B抑制剂的合成，结构-活性关系和对接研究

  摘要：

  28比1：不错的赔率：酪氨酸磷酸酶1B（PTP1B）是治疗2型糖尿病的有希望的靶标。合成了芳基噻唑基苯基磺酰胺，并在体外针对PTP1B进行了筛选。然后在链脲佐菌素诱导的（STZ）糖尿病大鼠模型中评估表现出> 48％抑制作用的化合物，从而鉴定出一种疗效与二甲双胍相当的化合物。最后，对接研究用于解释观察到的结构-活性关系。

  DOI：

  10.1002/cmdc.201200197

文献信息

• Synthesis and QSAR Studies in 2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole Derivatives as Potential Antithrombotic Agents
  作者：Anil K. Saxena、Suresh K. Pandey、P. Seth、M.P. Singh、M. Dikshit、A. Carpy

  DOI：10.1016/s0968-0896(01)00082-7

  日期：2001.8

  A series of 2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole derivatives have been synthesized via cyclocondensation of N-aryl thioureas with 2-bromoethylamine hydrobromide followed by the reaction of the product thus obtained with aroyl chlorides. Title compounds were evaluated for their antithrombotic activity in vivo in mice where one of these compound 29 provided 65% protection as compared to 77% protection offered by the standard Indomethacin. Quantitative Structure-Activity Relationship (QSAR) studies were performed on these compounds using physicochemical (hydrophobic, electronic, steric) parameter as independent and antithrombic activity as dependent parameter, where antithrombotic activity correlated best (r > 0.8) with electronic parameters (F, sigma or mu) having high statistical significance > 99.9% (F-2,F-22 > 15.0; F-2,F-22 alpha :0.001 = 11.0) suggesting that hydrophobic, steric and resonance factors are insignificant in this set of molecules for the activity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.
• Synthesis and biological evaluation of substituted 4-arylthiazol-2-amino derivatives as potent growth inhibitors of replicating Mycobacterium tuberculosis H37RV
  作者：Kuldeep K. Roy、Supriya Singh、Sandeep K. Sharma、Ranjana Srivastava、Vinita Chaturvedi、Anil K. Saxena

  DOI：10.1016/j.bmcl.2011.06.076

  日期：2011.9

  In search of potential therapeutics for tuberculosis, we describe herein synthesis and biological evaluation of some substituted 4-arylthiazol-2-amino derivatives as modified analogues of the antiprotozoal drug Nitazoxanide (NTZ), which has recently been reported as potent inhibitor of Mtb H(37)Rv (Mtb MIC = 52.12 mu M) with an excellent ability to evade resistance. Among the synthesized derivatives, the two compounds 7a ( MIC = 15.28 mu M) and 7c (MIC = 17.03 mu M) have exhibited about three times better Mtb growth inhibitory activity over NTZ and are free from any cytotoxicity (Vero CC50 of 244 and 300 mu M respectively). These two compounds represent promising leads for further optimization. (C) 2011 Elsevier Ltd. 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：——
• Mishra, Virendra, Acta Chimica Hungarica, 1990, vol. 127, p. 155 - 162
  作者：Mishra, Virendra

  DOI：——

  日期：——