4-((2-(4-phenylthiazol-2-yl)hydrazono)methyl)phenyl benzenesulfonate

• 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: 4-((2-(4-phenylthiazol-2-yl)hydrazono)methyl)phenyl benzenesulfonate
• 英文别名: [4-[[(4-phenyl-1,3-thiazol-2-yl)hydrazinylidene]methyl]phenyl] benzenesulfonate
• 化学式: C₂₂H₁₇N₃O₃S₂
• 分子量: 435.527
• InChiKey: ZAYJASMOXMCMLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.65
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-((2-(4-phenylthiazol-2-yl)hydrazono)methyl)phenyl benzenesulfonate 、 苯胺 在 盐酸 、 sodium nitrite 、 吡啶 作用下， 以 水 为溶剂， 反应 3.0h， 以60%的产率得到4-((2-(4-phenyl-5-(phenyldiazenyl)thiazol-2-yl)hydrazono)methyl)phenyl benzenesulfonate
  参考文献：
  名称：

  合成一些新型磺酸酯基杂环作为抗肿瘤剂的高效便捷途径

  摘要：

  In the present investigation, simple and straightforward methodology for the preparation of novel thiazolidinone, thiazole, pyridinone, chromene, pyrazole, benzimidazo[1,2-a]pyrimidine and thiazolo[3,2-a]pyrimidine derivatives bearing sulfonate ester moiety through the reaction of 4-formylphenyl benzenesulfonate (1) with some nitrogen nucleophiles such as hydrazine hydrate, thiosemicarbazide and 2-cyanoacetohydrazide is described. The antitumor activities were evaluated according to the protocol of the National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay against two human tumor cell lines namely; breast cancer MCF-7 and prostate cancer PC3. The results revealed that compounds (4), (7), (9), (13) and (16) exhibited promising antitumor activity in the two cell lines assay compared with 5-fluorouracil as a reference drug.

  DOI：

  10.3987/com-18-13870
• 作为产物：
  描述：

  (4-甲酰基苯基)苯磺酸盐 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 4-((2-(4-phenylthiazol-2-yl)hydrazono)methyl)phenyl benzenesulfonate
  参考文献：
  名称：

  合成一些新型磺酸酯基杂环作为抗肿瘤剂的高效便捷途径

  摘要：

  In the present investigation, simple and straightforward methodology for the preparation of novel thiazolidinone, thiazole, pyridinone, chromene, pyrazole, benzimidazo[1,2-a]pyrimidine and thiazolo[3,2-a]pyrimidine derivatives bearing sulfonate ester moiety through the reaction of 4-formylphenyl benzenesulfonate (1) with some nitrogen nucleophiles such as hydrazine hydrate, thiosemicarbazide and 2-cyanoacetohydrazide is described. The antitumor activities were evaluated according to the protocol of the National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay against two human tumor cell lines namely; breast cancer MCF-7 and prostate cancer PC3. The results revealed that compounds (4), (7), (9), (13) and (16) exhibited promising antitumor activity in the two cell lines assay compared with 5-fluorouracil as a reference drug.

  DOI：

  10.3987/com-18-13870

文献信息

• Efficient and Convenient Route to the Synthesis of Some Novel Sulfonate Ester-Based Heterocycles as Antitumor Agents
  作者：Ahmed El-Mekabaty、Osman M. O. Habib

  DOI：10.3987/com-18-13870

  日期：——

  In the present investigation, simple and straightforward methodology for the preparation of novel thiazolidinone, thiazole, pyridinone, chromene, pyrazole, benzimidazo[1,2-a]pyrimidine and thiazolo[3,2-a]pyrimidine derivatives bearing sulfonate ester moiety through the reaction of 4-formylphenyl benzenesulfonate (1) with some nitrogen nucleophiles such as hydrazine hydrate, thiosemicarbazide and 2-cyanoacetohydrazide is described. The antitumor activities were evaluated according to the protocol of the National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay against two human tumor cell lines namely; breast cancer MCF-7 and prostate cancer PC3. The results revealed that compounds (4), (7), (9), (13) and (16) exhibited promising antitumor activity in the two cell lines assay compared with 5-fluorouracil as a reference drug.