2-acetylpyridine-N(4)-ortho-fluorophenyl thiosemicarbazone | 70618-02-9

• 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: 2-acetylpyridine-N(4)-ortho-fluorophenyl thiosemicarbazone
• 英文别名: 2-acetylpyridine N(4)-(o-fluorophenyl)thiosemicarbazone；1-(2-Fluorophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea
• CAS: 70618-02-9
• 化学式: C₁₄H₁₃FN₄S
• 分子量: 288.348
• InChiKey: PMHTWYVKIPHSFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetylpyridine-N(4)-ortho-fluorophenyl thiosemicarbazone 、 三氯化锑 以 甲醇 为溶剂， 以93%的产率得到dichloro[N(4)-ortho-fluorophenyl-2-acetylpyridinethiosemicarbazonato]antimony(III)
  参考文献：
  名称：

  2-Acetylpyridine- and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity

  摘要：

  Complexes [Sb(2Ac4oClPh)Cl-2] (1), [Sb(2Ac4oFPh)Cl-2] (2), [Sb(2Ac4oNO(2)Ph)Cl-2] (3), [Sb(28z4oClPh)Cl-2] (4), [Sb(2Bz4oFPh)Cl-2] (5) and [Sb(2Bz4oNO(2)Ph)Cl-2] (6) were obtained with 2-acetylpyridine-N(4)-orthochlorophenyl thiosemicarbazone (H2Ac4oClPh) and its N(4)-ortho-fluor (H2Ac4oFPh) and N(4)-ortho-nitro (H2Ac4oNO(2)Ph) analogues, and with the corresponding 2-benzoylpyridine-derived thiosemicarbazones (H2Bz4oClPh, H2Bz4oFPh, H2Bz4oNO(2)Ph). The studied compounds are excellent inhibitors of Trypanosoma cruzi growth. H2Bz4oClPh and complexes (4) and (1) were the most trypanosomicidal.Upon coordination of H2Ac4oClPh to antimony(III) in 1, the therapeutic index (TI) goes from 10.58 to 14.35. However, the best values of TI were found for H2Bz4oClPh (TI = 1240) and H2Ac4oNO(2)Ph (TI = 773). Structure-activity relationship (SAR) studies did not allow the establishment of correlations between the anti-trypanosomal activity and physico-chemical parameters, but correlations were found between the cytotoxicities and physico-chemical properties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.10.018

文献信息

• Cytotoxic effects of indium(III) complexes with 2-acetylpyridine-N(4)-ortho-fluorophenylthiosemicarbazone and their radioactive 114mIn analogues against human glioma cells
  作者：Andrea R. Aguirre、Gabrieli L. Parrilha、Renata Diniz、Beatriz Cancelier Ribeiro、Raquel G. Dos Santos、Heloisa Beraldo

  DOI：10.1016/j.poly.2019.02.055

  日期：2019.5

  Complexes [ln(2Ac4oFPh)Cl-2(MeOH)] (1) and [In(2Ac4oFPh)Cl-2]center dot 0.5EtOH (2) were obtained with 2-acetylpyridine-N(4)-ortho-fluorophenyl thiosemicarbazone (H2Ac4oFPh). Neutron activation of I and 2 resulted in the formation of the In-114m/In-115m analogues (*1) and (*2). The thiosemicarbazone ligand, the non-radioactive and radioactive complexes were assayed for their cytotoxic effects against U87 human glioblastoma cells. While radioactive and non-radioactive InCl3 were devoid of cytotoxic activity, complexes (I) and (2) and their radioactive analogues (*1) and (*2) showed similar cytotoxic effects and were as active as the parent thiosemicarbazone against U87 glioma cells. Since the radioactive complexes revealed to keep the thiosemicarbazone cytotoxicity, if these complexes are produced with high specific activity, they might constitute an interesting platform for the development of prototype radiotracer drugs for treatment of glioma neoplasia by delivering high radiation dose to the tumor cells. (C) 2019 Elsevier Ltd. All rights reserved.