2-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one | 924864-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one
• 英文别名: 2-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one；2-[3-(4-Methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
• CAS: 924864-03-9
• 化学式: C₁₉H₁₇N₃O₂S
• 分子量: 351.429
• InChiKey: CZGCQVKQPNVWSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one 、 对二甲氨基苯甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 5.0h， 以59%的产率得到5-(4-dimethylaminobenzylidene)-2-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one
  参考文献：
  名称：

  含吡唑啉部分的新型噻唑酮类化合物的合成及其抗癌活性评估

  摘要：

  为了检查抗癌活性，获得了几种含有5-芳基-3-苯基-4，5-二氢-1 H-吡唑-1-基骨架的新型基于噻唑酮的化合物。5-芳基-3-苯基-4,5-二氢吡唑与4-硫代-2--2-噻唑烷酮或2-乙氧基甲硫基-2-噻唑啉-4-酮的反应生成起始4-（1和2）或2-取代（11和12），其中使用了Knoevenagel缩合获得一系列5-亚芳基衍生物的噻唑酮3 - 10，13 - 18。可替代地11，12并通过[2 + 3]-环缩合反应，以3-苯基-5-芳基-1-硫代氨基甲酰基-2-吡唑啉为S，N-双亲核试剂合成了它们的5-亚芳基衍生物。化合物的结构通过1 H，13 C NMR，LC-MS，EI-MS和X射线分析确定。在体外合成的化合物的抗癌活性是由国家癌症研究所测试，其中大部分显示在白血病，黑色素瘤，肺癌，结肠癌，中枢神经系统癌，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系中的抗癌活性。讨论了结构与活性之间的关

  DOI：

  10.1016/j.ejmech.2008.09.032
• 作为产物：
  描述：

  4-甲氧基查耳酮 在 sodium acetate 、 乙酸酐 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors

  摘要：

  A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 mu M for EGFR and IC50 = 1.07 mu M for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 mu M, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.051

文献信息

• Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
  作者：Ke-Ming Qiu、Hai-Hong Wang、Li-Ming Wang、Yin Luo、Xian-Hui Yang、Xiao-Ming Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.01.051

  日期：2012.3

  A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 mu M for EGFR and IC50 = 1.07 mu M for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 mu M, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Lucjusz Zaprutko、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.ejmech.2008.09.032

  日期：2009.4

  for obtaining a series of 5-arylidene derivatives 3–10, 13–18. Alternatively 11, 12 and their 5-arylidene derivatives were synthesized by means of 3-phenyl-5-aryl-1-thiocarbamoyl-2-pyrazoline as S,N-binucleophile via [2 + 3]-cyclocondensation approach. The structures of compounds were determined by 1H, 13C NMR, LC–MS, EI-MS and X-ray analysis. The in vitro anticancer activity of synthesized compounds

  为了检查抗癌活性，获得了几种含有5-芳基-3-苯基-4，5-二氢-1 H-吡唑-1-基骨架的新型基于噻唑酮的化合物。5-芳基-3-苯基-4,5-二氢吡唑与4-硫代-2--2-噻唑烷酮或2-乙氧基甲硫基-2-噻唑啉-4-酮的反应生成起始4-（1和2）或2-取代（11和12），其中使用了Knoevenagel缩合获得一系列5-亚芳基衍生物的噻唑酮3 - 10，13 - 18。可替代地11，12并通过[2 + 3]-环缩合反应，以3-苯基-5-芳基-1-硫代氨基甲酰基-2-吡唑啉为S，N-双亲核试剂合成了它们的5-亚芳基衍生物。化合物的结构通过1 H，13 C NMR，LC-MS，EI-MS和X射线分析确定。在体外合成的化合物的抗癌活性是由国家癌症研究所测试，其中大部分显示在白血病，黑色素瘤，肺癌，结肠癌，中枢神经系统癌，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系中的抗癌活性。讨论了结构与活性之间的关