2-acetylpyridine-N(4)-ortho-chlorophenyl thiosemicarbazone | 70618-05-2

• 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-chlorophenyl thiosemicarbazone
• 英文别名: N(4)-ortho-chlorophenyl-2-acetylpyridine thiosemicarbazone；2-acetylpyridine N(4)-(o-chlorophenyl)thiosemicarbazone；1-(2-chlorophenyl)-3-(1-pyridin-2-ylethylideneamino)thiourea
• CAS: 70618-05-2
• 化学式: C₁₄H₁₃ClN₄S
• 分子量: 304.803
• InChiKey: DIAIPLSVPPGTLG-UHFFFAOYSA-N

物化性质

• 沸点：
  438.0±51.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

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：

  2-acetylpyridine-N(4)-ortho-chlorophenyl thiosemicarbazone 、 三氯化锑 以 甲醇 为溶剂， 以94%的产率得到dichloro[N(4)-ortho-chlorophenyl-2-acetylpyridine thiosemicarbazonato]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
• 作为产物：
  描述：

  2-乙酰基吡啶 、 2-氯苯基异氰酸酯 在 肼 作用下， 生成 2-acetylpyridine-N(4)-ortho-chlorophenyl thiosemicarbazone
  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

• 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
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