3-(2-Hydroxyphenyl)-5-phenyl-3,4-dihydropyrazole-2-carbothioamide | 475115-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-Hydroxyphenyl)-5-phenyl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 475115-23-2
• 化学式: C₁₆H₁₅N₃OS
• 分子量: 297.381
• InChiKey: YLYXKPTXJCYMDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴苯乙酮 、 3-(2-Hydroxyphenyl)-5-phenyl-3,4-dihydropyrazole-2-carbothioamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以90.4%的产率得到2-[2-[4-(3-Methoxyphenyl)-1,3-thiazol-2-yl]-5-phenyl-3,4-dihydropyrazol-3-yl]phenol
  参考文献：
  名称：

  Dihydropyrazothiazole derivatives as potential MMP-2/MMP-8 inhibitors for cancer therapy

  摘要：

  MMP-2/MMP-8 is established as one of the most important metalloenzymes for targeting cancer. A series of dihydropyrazothiazole derivatives (E1-E18) bearing a salicylaldehyde group linked to Pyrazole ring were designed, synthesized, and evaluated for their pharmacological activity as MMP-2/MMP-8 inhibitors. Among them, compound E17 exhibited most potent inhibitory activity (IC50 = 2.80 mu M for MMP-2 and IC50 = 5.6 mu M for MMP-8), compared to the positive drug CMT-1 (IC50 = 1.29 mu M). Compounds (E1-E18) were scrutinized by CoMFA and CoMSIA techniques of Three-dimensional quant. structure-activity relationship (3D-QSAR), as well as a docking simulation. Moreover, treatment with compound E4 could induce MCF-7 cell apoptosis. Overall, the biological profile of E1-E18 may provide a research basis for the development of new agents against cancer. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2018.05.004
• 作为产物：
  描述：

  水杨醛 在 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 12.0h， 生成 3-(2-Hydroxyphenyl)-5-phenyl-3,4-dihydropyrazole-2-carbothioamide
  参考文献：
  名称：

  Dihydropyrazothiazole derivatives as potential MMP-2/MMP-8 inhibitors for cancer therapy

  摘要：

  MMP-2/MMP-8 is established as one of the most important metalloenzymes for targeting cancer. A series of dihydropyrazothiazole derivatives (E1-E18) bearing a salicylaldehyde group linked to Pyrazole ring were designed, synthesized, and evaluated for their pharmacological activity as MMP-2/MMP-8 inhibitors. Among them, compound E17 exhibited most potent inhibitory activity (IC50 = 2.80 mu M for MMP-2 and IC50 = 5.6 mu M for MMP-8), compared to the positive drug CMT-1 (IC50 = 1.29 mu M). Compounds (E1-E18) were scrutinized by CoMFA and CoMSIA techniques of Three-dimensional quant. structure-activity relationship (3D-QSAR), as well as a docking simulation. Moreover, treatment with compound E4 could induce MCF-7 cell apoptosis. Overall, the biological profile of E1-E18 may provide a research basis for the development of new agents against cancer. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2018.05.004

文献信息

• Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1021/jm300789g

  日期：2012.10.25

  The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia

  新型3- [2-（3,5-二芳基-4,5-二氢吡唑-1-基）-4-氧代-4,5-二氢-1,3-噻唑-5-亚烷基的合成及抗肿瘤活性的筛选] -2,3-dihydro-1 H-吲哚-2-ones 1 – 23和3-（3,5-diarylpyrazol-1-yl）-2,3-dihydro-1 H -indol-2-ones 24 –执行39次。美国国家癌症研究所测试了合成化合物的体外抗癌活性。他们中的大多数对白血病，黑素瘤，肺癌，结肠癌，中枢神经系统，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系均表现出抗癌活性。讨论了构效关系。发现最有效的抗癌化合物10具有平均GI 50的活性TGI值分别为0.071μM和0.76μM。它显示出对非小细胞肺癌细胞HOP-92（GI 50 <0.01μM），结肠癌细胞系HCT-116（GI 50 = 0.018μM），CNS癌细胞SNB-75（ GI 50 = 0.0159μM），卵巢癌细胞系NCI
• 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
• Malhotra, Vineet; Pathak, Seema; Nath, Rajendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 6, p. 1310 - 1313
  作者：Malhotra, Vineet、Pathak, Seema、Nath, Rajendra、Mukerjee, Devashis、Shanker, Kirpa

  DOI：——

  日期：——