2-acetylpyridine N(4)-para-iodophenylthiosemicarbazone | 1379521-69-3

• 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: 2-acetylpyridine N(4)-para-iodophenylthiosemicarbazone
• 英文别名: N(4)-para-iodophenyl-2-acetylpyridine thiosemicarbazone；1-(4-Iodophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea
• CAS: 1379521-69-3
• 化学式: C₁₄H₁₃IN₄S
• 分子量: 396.255
• InChiKey: NRNNRLWHLIPYQW-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：

  indium nitrate hydrate 、 2-acetylpyridine N(4)-para-iodophenylthiosemicarbazone 以 甲醇 为溶剂， 反应 4.0h， 以82%的产率得到bis[N(4)-para-iodophenyl-2-acetylpyridinethiosemicarbazonato]indium(III) nitrate hydrate
  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

文献信息

• Cytotoxic and antimicrobial effects of indium(<scp>iii</scp>) complexes with 2-acetylpyridine-derived thiosemicarbazones
  作者：Alexandre A. Oliveira、Gabriele M. C. Perdigão、Luana E. Rodrigues、Jeferson G. da Silva、Elaine M. Souza-Fagundes、Jacqueline A. Takahashi、Willian R. Rocha、Heloisa Beraldo

  DOI：10.1039/c6dt03657k

  日期：——

  (SI) increased in several cases for the indium(III) complexes in comparison with the free thiosemicarbazones. The antimicrobial activity of the compounds was investigated against Candida albicans, Candida dubliniensis, Candida lusitaniae and Candida parapsilosis. In many cases complexation resulted in a substantial increase of the antifungal activity. Complexes (1–4) were revealed to be very active against

  配合物[In（2Ac4 o ClPh）Cl 2（MeOH）]（1），[In（2Ac4 p FPh）Cl 2（MeOH）]（2），[In（2Ac4 p ClPh）Cl 2（MeOH）]（3）和[In（2Ac4 p IPh）Cl 2（MeOH）]（4）是由N（4）-邻-氯苯基-2-乙酰基吡啶硫代半碳酮（H2Ac4 o ClPh），N（4）-对-氟苯基-2 -乙酰吡啶硫代半碳酮（H2Ac4 p FPh），N（4）-对-氯苯基-2-乙酰基吡啶硫代半碳酸盐（H2Ac4 p ClPh）和N（4）-对-碘苯基-2-乙酰基吡啶硫代半碳酸盐（H2Ac4p I Ph）。理论研究表明，配位甲醇分子很容易被制备储备溶液中使用的DMSO取代，形成[In（L）Cl 2（DMSO）]（HL =硫代半氨基甲酸酯配体），不利于用水代替DMSO。然而，对于所有配合物，在水溶液中用水置换一或两个氯化物配体是极其有利的。评价了化
• Gallium(III) complexes with 2-acetylpyridine-derived thiosemicarbazones: antimicrobial and cytotoxic effects and investigation on the interactions with tubulin
  作者：Josane A. Lessa、Marcella A. Soares、Raquel G. dos Santos、Isolda C. Mendes、Lívia B. Salum、Hikmat N. Daghestani、Adriano D. Andricopulo、Billy W. Day、Andreas Vogt、Heloisa Beraldo

  DOI：10.1007/s10534-012-9603-1

  日期：2013.2

  ), 2-acetylpyridine N(4)-para-nitrophenyl-(H2Ac4pNO(2)Ph) and 2-acetylpyridine N(4)-para-tolyl-(H2Ac4pT) thiosemicarbazone. 1-5 presented antimicrobial and cytotoxic properties. Coordination to gallium(III) proved to be an effective strategy for activity improvement against Pseudomonas aeruginosa and Candida albicans. The complexes were highly cytotoxic against malignant glioblastoma and breast cancer

  配合物[Ga（2Ac4pFPh）（2）] NO（3）（1），[Ga（2Ac4pClPhPh（2）] NO（3）（2），[Ga（2Ac4pIPhh（2）] NO（3）（3 ），用2-获得[Ga（2Ac4pNO（2）Ph）（2）] NO（3）·3H（2）O（4）和[Ga（2Ac4pT）（2）] NO（3）（5）乙酰基吡啶N（4）-对氟苯基-（H2Ac4pFPh），2-乙酰基吡啶N（4）-对氯苯基-（H2Ac4pClPh），2-乙酰基吡啶N（4）-对碘苯基-（H2Ac4pIPh），2-乙酰基吡啶N （4）-对硝基苯基-（H2Ac4pNO（2）Ph）和2-乙酰基吡啶N（4）-对甲苯基-（H2Ac4pT）硫代半脲。1-5显示了抗微生物和细胞毒性特性。与镓（III）的配位被证明是改善铜绿假单胞菌和白色念珠菌活性的有效策略。该复合物对纳摩尔浓度的恶性胶质母细胞瘤和乳腺癌细胞具有高度的细胞毒性。该化合物在
• 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.