1-(3-chlorophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea | 70618-06-3

• 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: 1-(3-chlorophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea
• CAS: 70618-06-3
• 化学式: C₁₄H₁₃ClN₄S
• 分子量: 304.803
• InChiKey: QJEQNMXYYQUOAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-chlorophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea 、 indium nitrate hydrate 以 甲醇 为溶剂， 反应 4.0h， 以80%的产率得到bis[N(4)-meta-chlorophenyl-2-acetylpyridinethiosemicarbazonato]indium(III) nitrate sesquihydrate
  参考文献：
  名称：

  Indium(III) complexes with 2-acetylpyridine-derived thiosemicarbazones exhibit cytotoxic activity against human leukemia and solid tumor cell lines

  摘要：

  Complexes [In(2Ac4Ph)(2)]NO3 center dot H2O (1), [In(2Ac4mClPh)(2)]NO3 center dot 1.5H(2)O (2), [In(2Ac4pClPh)(2)]NO3 center dot 2H(2)O (3) and [In(2Ac4plPh)(2)]NO3 center dot H2O (4) were obtained with N(4)-phenyl-2-acetylpyridine thiosemicarbazone (H2Ac4Ph), and its N(4)-meta-chlorophenyl-(H2Ac4mClPh), N(4)-para-chlorophenyl-(H2Ac4pClPh) and N(4)-para-iodophenyl-(H2Ac4plPh) derivatives. The crystal structures of [In(2Ac4Ph)2]NO3 center dot MeOH (1a), [In(2Ac4mClPh)(2)]NO3 center dot EtOH center dot H2O (2a) and [In(2Ac4pClPh)(2)]center dot NO3 (3a) were determined. The cytotoxic effects of the thiosemicarbazone ligands and of complexes (1-4) were evaluated against HL-60, Jurkat and THP-1 leukemia cells and against MCF-7, MDA-MB-231 and HCT-116 solid tumor cells, as well as against mammalian healthy Vero cells. Upon coordination to indium(III) cytotoxicity increased in several cases. In addition, complex (1) was active in sub-micromolar doses against all tested cell lineages, with selectivity indexes (SI = IC50 (vero)/lC(50) tumor cell) ranging from 3 (against THP-1 cells) to 144 (against HCT-116 cells). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.06.045
• 作为产物：
  描述：

  2-乙酰基吡啶 、 3-氯异硫氰酸苯酯 在 肼 作用下， 生成 1-(3-chlorophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea
  参考文献：
  名称：

  N 4-苯基取代的2-乙酰基吡啶硫代半氨基甲酮：对人肿瘤细胞的细胞毒性，结构-活性关系研究和作用机理的研究

  摘要：

  Ñ 4 -苯基2-乙酰基吡啶缩氨基硫脲（H2Ac4Ph; ñ - （苯基）-2-（1-（吡啶-2-基）亚乙基）肼硫代甲酰胺）及其Ñ 4 -邻- ， -元-和-对氟苯基（ H2Ac4 ø FPH，H2Ac4米FPH，H2Ac4 p FPH），ñ 4 -邻- ， -元-和-对氯苯基（H2Ac4 ø CLPH，H2Ac4米CLPH，H2Ac4 p CLPH），ñ 4 -邻- ， -元-和 -对碘苯基（H2Ac4 ø IPH，H2Ac4米IPH，H2Ac4 p IPH）和Ñ 4 -邻- ， -元-和-对硝基苯基（H2Ac4 ö NO 2 PH，H2Ac4米NO 2 PH，H2Ac4 p NO 2 PH）分析了这些衍生物对人恶性乳腺癌（MCF-7）和神经胶质瘤（T98G和U87）细胞的细胞毒性。这些化合物对三种细胞谱系均具有高度的细胞毒性（IC 50：MCF-7，52-0.16 nM；T98G，140-1

  DOI：

  10.1016/j.bmc.2012.04.027

文献信息

• N4-Phenyl-substituted 2-acetylpyridine thiosemicarbazones: Cytotoxicity against human tumor cells, structure–activity relationship studies and investigation on the mechanism of action
  作者：Marcella A. Soares、Josane A. Lessa、Isolda C. Mendes、Jeferson G. Da Silva、Raquel G. dos Santos、Lívia B. Salum、Hikmat Daghestani、Adriano D. Andricopulo、Billy W. Day、Andreas Vogt、Jorge L. Pesquero、Willian R. Rocha、Heloisa Beraldo

  DOI：10.1016/j.bmc.2012.04.027

  日期：2012.6

  N4-Phenyl 2-acetylpyridine thiosemicarbazone (H2Ac4Ph; N-(phenyl)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide) and its N4-ortho-, -meta- and -para-fluorophenyl (H2Ac4oFPh, H2Ac4mFPh, H2Ac4pFPh), N4-ortho-, -meta- and -para-chlorophenyl (H2Ac4oClPh, H2Ac4mClPh, H2Ac4pClPh), N4-ortho-, -meta- and -para-iodophenyl (H2Ac4oIPh, H2Ac4mIPh, H2Ac4pIPh) and N4-ortho-, -meta- and -para-nitrophenyl

  Ñ 4 -苯基2-乙酰基吡啶缩氨基硫脲（H2Ac4Ph; ñ - （苯基）-2-（1-（吡啶-2-基）亚乙基）肼硫代甲酰胺）及其Ñ 4 -邻- ， -元-和-对氟苯基（ H2Ac4 ø FPH，H2Ac4米FPH，H2Ac4 p FPH），ñ 4 -邻- ， -元-和-对氯苯基（H2Ac4 ø CLPH，H2Ac4米CLPH，H2Ac4 p CLPH），ñ 4 -邻- ， -元-和 -对碘苯基（H2Ac4 ø IPH，H2Ac4米IPH，H2Ac4 p IPH）和Ñ 4 -邻- ， -元-和-对硝基苯基（H2Ac4 ö NO 2 PH，H2Ac4米NO 2 PH，H2Ac4 p NO 2 PH）分析了这些衍生物对人恶性乳腺癌（MCF-7）和神经胶质瘤（T98G和U87）细胞的细胞毒性。这些化合物对三种细胞谱系均具有高度的细胞毒性（IC 50：MCF-7，52-0.16 nM；T98G，140-1
• Indium(III) complexes with 2-acetylpyridine-derived thiosemicarbazones exhibit cytotoxic activity against human leukemia and solid tumor cell lines
  作者：Alexandre A. Oliveira、Gabriele M.C. Perdigão、Jeferson G. da Silva、Elaine M. Souza-Fagundes、Heloisa Beraldo

  DOI：10.1016/j.poly.2017.06.045

  日期：2017.10

  Complexes [In(2Ac4Ph)(2)]NO3 center dot H2O (1), [In(2Ac4mClPh)(2)]NO3 center dot 1.5H(2)O (2), [In(2Ac4pClPh)(2)]NO3 center dot 2H(2)O (3) and [In(2Ac4plPh)(2)]NO3 center dot H2O (4) were obtained with N(4)-phenyl-2-acetylpyridine thiosemicarbazone (H2Ac4Ph), and its N(4)-meta-chlorophenyl-(H2Ac4mClPh), N(4)-para-chlorophenyl-(H2Ac4pClPh) and N(4)-para-iodophenyl-(H2Ac4plPh) derivatives. The crystal structures of [In(2Ac4Ph)2]NO3 center dot MeOH (1a), [In(2Ac4mClPh)(2)]NO3 center dot EtOH center dot H2O (2a) and [In(2Ac4pClPh)(2)]center dot NO3 (3a) were determined. The cytotoxic effects of the thiosemicarbazone ligands and of complexes (1-4) were evaluated against HL-60, Jurkat and THP-1 leukemia cells and against MCF-7, MDA-MB-231 and HCT-116 solid tumor cells, as well as against mammalian healthy Vero cells. Upon coordination to indium(III) cytotoxicity increased in several cases. In addition, complex (1) was active in sub-micromolar doses against all tested cell lineages, with selectivity indexes (SI = IC50 (vero)/lC(50) tumor cell) ranging from 3 (against THP-1 cells) to 144 (against HCT-116 cells). (C) 2017 Elsevier Ltd. All rights reserved.