4-amino-3-phenyl-5[(1-phenyl-3,5-dimethylpyrazol-4-yl)methylidinehydrazinocarbonyl]thiazole-2(3H)-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-3-phenyl-5[(1-phenyl-3,5-dimethylpyrazol-4-yl)methylidinehydrazinocarbonyl]thiazole-2(3H)-thione
• 英文别名: 4-amino-N-[(E)-(3,5-dimethyl-1-phenylpyrazol-4-yl)methylideneamino]-3-phenyl-2-sulfanylidene-1,3-thiazole-5-carboxamide
• 化学式: C₂₂H₂₀N₆OS₂
• 分子量: 448.572
• InChiKey: RDIMAXBLZJLZKT-ZMOGYAJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 4-amino-3-phenyl-5[(1-phenyl-3,5-dimethylpyrazol-4-yl)methylidinehydrazinocarbonyl]thiazole-2(3H)-thione 在 sodium hydroxide 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75.3%的产率得到6-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-meth-(E)-ylideneamino)-5-mercapto-3-phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one
  参考文献：
  名称：

  Synthesis and Antitumor Evaluation of New Polysubstituted Thiazole and Derived Thiazolo[4, 5-d]pyrimidine Systems

  摘要：

  The synthesis of three categories of compounds containing the 1 H-pyrazole ring linked to some dihydrothiazoles, thiazolidinones, and thiazolo[4,5-d]pyrimidines through different linkages is described. Nine of the newly synthesized target compounds were selected by the NCI for in-vitro antitumor screening. Four compounds, namely 4 a, 4 b, 13, and 14, exhibited a broad spectrum of antitumor activity against most of the tested tumor cell lines. Compound 4a, 3-phenyl-4-amino-5-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-methylidenehydrazinocarbonyl)thiazole-2(3H)thione proved to be the most active antitumor agent in the present study with GI(50), TGI, and LC50 MG-MID values of 3.93, 41.7, and 91.2 muM, respectively. The same compound also exhibited high selectivity towards CNS SNB-75 and Ovarian IGROV1 cancer cell lines at both the GI(50) and TGI levels. Compound 4 b, 3-(4-chlorophenyl)-4-amino-5-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-methylidenehydrazinocarbonyl)thiazole-2(3H)-thione showed nearly the same pattern of activity as 4 a but to a lesser extent. Compounds 13 and 14 displayed moderate antitumor activity against most of the tested tumor cell lines with GI(50). MG-MID values range of 20.4-80.6 muM and TGI MG-MID values of 55.5-95.5 muM.

  DOI：

  10.1002/1521-4184(200205)335:5<213::aid-ardp213>3.0.co;2-h
• 作为产物：
  描述：

  3,5-二甲基-1苯基吡唑-4-噻吩甲醛 在 sulfur 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-amino-3-phenyl-5[(1-phenyl-3,5-dimethylpyrazol-4-yl)methylidinehydrazinocarbonyl]thiazole-2(3H)-thione
  参考文献：
  名称：

  Synthesis and Antitumor Evaluation of New Polysubstituted Thiazole and Derived Thiazolo[4, 5-d]pyrimidine Systems

  摘要：

  The synthesis of three categories of compounds containing the 1 H-pyrazole ring linked to some dihydrothiazoles, thiazolidinones, and thiazolo[4,5-d]pyrimidines through different linkages is described. Nine of the newly synthesized target compounds were selected by the NCI for in-vitro antitumor screening. Four compounds, namely 4 a, 4 b, 13, and 14, exhibited a broad spectrum of antitumor activity against most of the tested tumor cell lines. Compound 4a, 3-phenyl-4-amino-5-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-methylidenehydrazinocarbonyl)thiazole-2(3H)thione proved to be the most active antitumor agent in the present study with GI(50), TGI, and LC50 MG-MID values of 3.93, 41.7, and 91.2 muM, respectively. The same compound also exhibited high selectivity towards CNS SNB-75 and Ovarian IGROV1 cancer cell lines at both the GI(50) and TGI levels. Compound 4 b, 3-(4-chlorophenyl)-4-amino-5-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-methylidenehydrazinocarbonyl)thiazole-2(3H)-thione showed nearly the same pattern of activity as 4 a but to a lesser extent. Compounds 13 and 14 displayed moderate antitumor activity against most of the tested tumor cell lines with GI(50). MG-MID values range of 20.4-80.6 muM and TGI MG-MID values of 55.5-95.5 muM.

  DOI：

  10.1002/1521-4184(200205)335:5<213::aid-ardp213>3.0.co;2-h

文献信息

• Synthesis and Antitumor Evaluation of New Polysubstituted Thiazole and Derived Thiazolo[4, 5-d]pyrimidine Systems
  作者：Hesham T. Y. Fahmy、Sherif A. F. Rostom、Adnan A. Bekhit

  DOI：10.1002/1521-4184(200205)335:5<213::aid-ardp213>3.0.co;2-h

  日期：2002.5

  The synthesis of three categories of compounds containing the 1 H-pyrazole ring linked to some dihydrothiazoles, thiazolidinones, and thiazolo[4,5-d]pyrimidines through different linkages is described. Nine of the newly synthesized target compounds were selected by the NCI for in-vitro antitumor screening. Four compounds, namely 4 a, 4 b, 13, and 14, exhibited a broad spectrum of antitumor activity against most of the tested tumor cell lines. Compound 4a, 3-phenyl-4-amino-5-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-methylidenehydrazinocarbonyl)thiazole-2(3H)thione proved to be the most active antitumor agent in the present study with GI(50), TGI, and LC50 MG-MID values of 3.93, 41.7, and 91.2 muM, respectively. The same compound also exhibited high selectivity towards CNS SNB-75 and Ovarian IGROV1 cancer cell lines at both the GI(50) and TGI levels. Compound 4 b, 3-(4-chlorophenyl)-4-amino-5-(3,5-dimethyl-1-phenyl-1H-pyrazole-4-methylidenehydrazinocarbonyl)thiazole-2(3H)-thione showed nearly the same pattern of activity as 4 a but to a lesser extent. Compounds 13 and 14 displayed moderate antitumor activity against most of the tested tumor cell lines with GI(50). MG-MID values range of 20.4-80.6 muM and TGI MG-MID values of 55.5-95.5 muM.