N-[(3-chlorophenyl)methylideneamino]-4-methyl-1,3-thiazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[(3-chlorophenyl)methylideneamino]-4-methyl-1,3-thiazol-2-amine
• 化学式: C₁₁H₁₀ClN₃S
• 分子量: 251.739
• InChiKey: DFVLNPLLRVKHBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 N-[(3-chlorophenyl)methylideneamino]-4-methyl-1,3-thiazol-2-amine 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis, Anticancer Activity, and Genome Profiling of Thiazolo Arene Ruthenium Complexes

  摘要：

  Sixteen hydrazinyl-thiazolo arene ruthenium complexes of the general formula [(eta(6)-p-cymene)Ru(N,Mhydrazinyl-thiazolo)Cl]Cl were synthesized. All complexes were tested in vitro for their antiproliferative activity on three tumor cell lines (HeLa, A2780, and A2780cisR) and on a noncancerous cell line (HFL-1). A superior cytotoxic activity of the ruthenium complexes as compared to cisplatin and oxaliplatin, on both cisplatin-sensitive and cisplatin resistant ovarian cancer cells, was observed. In addition, the biological activity of two selected derivatives was evaluated using microarray gene expression assay and ingenuity pathway analysis. p53 signaling was identified as an important pathway modulated by both arene ruthenium compounds. New activated molecules such as FAS, ZMAT3, PRMT2, BBC3/PUMA, and PDCD4, whose overexpressions are correlated with overcoming resistance to cisplatin therapy, were also identified as potential targets. Moreover, the arene ruthenium complexes can be used in association with cisplatin to prevent cisplatin resistance development and synergistically to induce cell death in ovarian cancer cells.

  DOI：

  10.1021/acs.jmedchem.5b00855