2-[2-(3-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole | 464200-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-(3-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole
• 英文别名: N-[(3-chlorophenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• CAS: 464200-09-7
• 化学式: C₁₆H₁₂ClN₃S
• 分子量: 313.81
• InChiKey: YQLJLBATSVXDJF-UHFFFAOYSA-N

物化性质

• 沸点：
  496.6±47.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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 、 2-[2-(3-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole 以 二氯甲烷 为溶剂， 反应 0.5h， 以61%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
• 作为产物：
  描述：

  氨基硫脲 、 3-氯苯甲醛 、 2-溴苯乙酮 以 水 为溶剂， 反应 2.0h， 以89%的产率得到2-[2-(3-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole
  参考文献：
  名称：

  超声辐射下水中N-（4-芳基噻唑-2-基）的高效一锅三组分合成。

  摘要：

  N-（4-芳基噻唑-2-基）hydr的高效，便捷的一锅三组分合成法在超声波照射下在水中无催化剂的情况下以优异的收率进行。

  DOI：

  10.1016/j.ultsonch.2011.10.017

文献信息

• Efficient one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones in water under ultrasound irradiation
  作者：Dong-Nuan Zhang、Ji-Tai Li、Ya-Li Song、Hui-Min Liu、Hong-Ya Li

  DOI：10.1016/j.ultsonch.2011.10.017

  日期：2012.5

  A highly efficient and facile one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones was carried out in excellent yield without any catalyst in water under ultrasound irradiation.

  N-（4-芳基噻唑-2-基）hydr的高效，便捷的一锅三组分合成法在超声波照射下在水中无催化剂的情况下以优异的收率进行。
• Synthesis, Anticancer Activity, and Genome Profiling of Thiazolo Arene Ruthenium Complexes
  作者：Adriana Grozav、Ovidiu Balacescu、Loredana Balacescu、Thomas Cheminel、Ioana Berindan-Neagoe、Bruno Therrien

  DOI：10.1021/acs.jmedchem.5b00855

  日期：2015.11.12

  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.