2-acetylpyridine-para-chloro-phenylhydrazone

• 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-para-chloro-phenylhydrazone
• 英文别名: 2-acetylpyridine-para-chlorophenylhydrazone；H2AcpClPh；2-Acetylpyridine 4-chlorobenzoylhydrazone；4-chloro-N-(1-pyridin-2-ylethylideneamino)benzamide
• 化学式: C₁₄H₁₂ClN₃O
• 分子量: 273.722
• InChiKey: BRPAABKVWTVIPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氯化锑 、 2-acetylpyridine-para-chloro-phenylhydrazone 以 甲醇 为溶剂， 反应 4.0h， 以68%的产率得到[2-acetylpyridine-para-chlorophenylhydrazonato(dichloro)antimony(III)]
  参考文献：
  名称：

  Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones

  摘要：

  Antimony(III) [Sb(L)Cl-2] complexes were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph) and 2-acetylpyridine-para-hydroxy-phenylhydrazone (H2AcpOHPh) along with the 2-benzoylpyridine-phenylhydrazone analogs H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh (HL). [Sb(2BzpClPh)Cl-2], complex (6), (IC50 = 4.91 +/- 1.20 mu mol L-1) was as active as nystatin (IC50= 4.44 +/- 0.76 mu mol L-1) and twofold more active than H2BzpClPh (IC50= 10.05 +/- 0.67 mu mol L-1) against Candida dubliniensis. While H2BzpClPh proved to be inactive against Candida glabrata, 6 (IC50 = 10.11 +/- 0.64 mu mol L-1) was more active than miconazole nitrate (IC50= 19.50 +/- 4.53 mu mol L-1). Similarly, H2BzpNO(2)Ph revealed to be inactive against Candida lusitaniae whereas complex [Sb(2BzpNO(2)Ph)Cl-2] (7) (IC50 = 8.54 +/- 2.21 mu mol L-1) proved to be as active as nystatin (IC50 = 5.31 +/- 0.84 mu mol L-1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.05.004
• 作为产物：
  描述：

  2-乙酰基吡啶 、 4-氯苯甲酰肼 以 1,2-丙二醇 、 二甲基亚砜 为溶剂， 生成 2-acetylpyridine-para-chloro-phenylhydrazone
  参考文献：
  名称：

  Screening a small hydrazide-hydrazone combinatorial library for targeting the STAT3 in monocyte-macrophages with insulated reporter transposons

  摘要：

  摘要 信号转导和转录激活因子3（STAT3）药物靶向被认为是治疗癌症、自身免疫性疾病或炎症性疾病的一种前瞻性方法。我们开发了一系列STAT3、NF-κB、Nrf2、金属反应性转录因子-1（MTF-1）和缺氧诱导因子1α（HIF-1α）在人单核-巨噬细胞系THP-1中转录激活的报告基因。这些报告基因被用来测试一组作为潜在 STAT3 抑制剂的酰肼。由 7 个羰基成分和 10 个酰肼成分的 70 个二元组合组成的酰肼-酰腙库，包括 STAT3 抑制剂临床药物硝呋沙齐，已经组装完成并通过报告基因筛选。就整个库而言，在 THP-1 单核细胞中发现 STAT3 和 NF-κB 或 STAT3 和 HIF-1α 报告物的反应之间存在明显的相关性。针对选定的抑制组合，制备了相应的酰肼，并进行了单独测试。在 THP-1 细胞中，最有效的 2-乙酰基吡啶-4-氯苯甲酰腙对 STAT3 的抑制潜力明显超过硝呋沙齐（ED50 分别为 2 和 50 μM）。我们的结论是，绝缘报告转座子可能是药物发现应用的有用工具。 图表摘要

  DOI：

  10.1007/s00044-023-03028-8

文献信息

• Synthesis, structural characterization and catalytic transfer hydrogenation of ruthenium(II) carbonyl complexes bearing N,N,O pincer type benzoylhydrazone ligands
  作者：Pandimuni Kalpaga Suganthy、Rupesh Narayana Prabhu、Venugopal Shanmugham Sridevi

  DOI：10.1016/j.poly.2014.12.016

  日期：2015.3

  as by elemental (C,H,N) analysis. A single crystal X-ray diffraction study of a representative complex, [Ru(L1)Cl(CO)(PPh 3 )] ( 1 ), confirms a pincer-like N,N,O coordination mode of the benzoylhydrazone ligand via the pyridine N, the azomethine N and the deprotonated amide O atoms, with the formation of two five-membered fused chelate rings, and indicates a distorted octahedral geometry around the

  摘要方便地合成了四个新的通式为[Ru（L）Cl（CO）（PPh 3）]的八面体钌（II）羰基苯甲酰hydr配合物（其中HL =取代的2-乙酰基吡啶苯甲酰hydr； H表示可解离的质子）已进行了描述。通过光谱（FT-IR，1 H NMR，UV-Vis）技术以及元素（C，H，N）分析可完成对配合物的表征。代表性配合物[Ru（L1）Cl（CO）（PPh 3）]（1）的单晶X射线衍射研究证实了苯甲酰hydr配体通过吡啶的类似钳状的N，N，O配位模式N，偶氮甲碱N和去质子化的酰胺O原子，形成两个五元稠合的螯合环，表明钌（II）中心周围的八面体几何形状失真。进一步，已经研究了配合物1对于取代的苯乙酮向相应的仲醇转移氢化的催化效率。还评估了碱和催化剂负载量在转移氢化反应中的影响。发现该配合物是在异丙醇/ KOH存在下的有效催化剂，转化率高达99.2％。
• Tricarbonylrhenium(<scp>i</scp>) complexes with 2-acetylpyridine-derived hydrazones are cytotoxic to NCI-H460 human large cell lung cancer
  作者：Camila Vargas Garcia、Gabrieli Lessa Parrilha、Bernardo Lages Rodrigues、Sarah Fernandes Teixeira、Ricardo Alexandre de Azevedo、Adilson Kleber Ferreira、Heloisa Beraldo

  DOI：10.1039/c6nj00050a

  日期：——

  cancer. Complexes (2) and (3) induced apoptosis on NCI-H460 cells. Complex (2) induced mitochondrial damage while treatment with 3 showed a later response, suggesting that probably the same effect would be observed at higher concentrations or longer treatments. Both complexes (2) and (3) showed a high antioxidant activity, 2 being more potent in reducing intracellular reactive oxygen species (ROS) production

  络合物[ReCl（CO）3（H2AcPh）]（1），[ReCl（CO）3（H2Ac p ClPh）]·0.5C 7 H 8（2）和[ReCl（CO）3（H2Ac p NO 2 Ph）用2-乙酰基吡啶-苯基hydr（H2AcPh）及其对-氯苯基hydr （H2Ac p ClPh）和对-硝基苯基hydr（H2Ac p NO 2 Ph）类似物获得]·0.5C 7 H 8（3）。协调tricarbonylrhenium（我）对NCI-H460人大细胞肺癌具有更高的抗增殖活性。复合物（2）和（3）诱导NCI-H460细胞凋亡。复合物（2）诱导线粒体损伤，而用3处理则显示出较晚的响应，这表明在更高浓度或更长的治疗时间可能会观察到相同的效果。配合物（2）和（3）均显示出高的抗氧化活性，2在减少细胞内活性氧（ROS）产生方面更有效。
• Silver(<scp>i</scp>) complexes with 2-acetylpyridinebenzoylhydrazones exhibit antimicrobial effects against yeast and filamentous fungi
  作者：Ane F. Santos、Isabella P. Ferreira、Jacqueline A. Takahashi、Gabriel L. S. Rodrigues、Carlos B. Pinheiro、Letícia R. Teixeira、Willian R. Rocha、Heloisa Beraldo

  DOI：10.1039/c7nj04280a

  日期：——

  2-Acetylpyridinebenzoylhydrazones and their silver(i) complexes show antimicrobial effects and deserve to be investigated as antifungal drug candidates.

  2-乙酰基吡啶苯甲酰肼及其银（i）配合物表现出抗微生物作用，值得作为抗真菌药物候选进行研究。
• Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
  作者：Isabella P. Ferreira、Elisa D.L. Piló、Angel A. Recio-Despaigne、Jeferson G. Da Silva、Jonas P. Ramos、Lucas B. Marques、Pedro H.D.M. Prazeres、Jacqueline A. Takahashi、Elaine M. Souza-Fagundes、Willian Rocha、Heloisa Beraldo

  DOI：10.1016/j.bmc.2016.05.007

  日期：2016.7

  Complexes [Bi(2AcPh)Cl-2]center dot 0.5H(2)O (1), [Bi(2AcpClPh)Cl-2] (2), [Bi(2AcpNO(2)Ph)Cl-2] (3), [Bi(2AcpOHPh)Cl-2]center dot 2H(2)O (4), [Bi(H2BzPh)Cl-3]center dot 2H(2)O (5), [Bi(H2BzpClPh)Cl-3] (6), [Bi(2BzpNO(2)Ph)Cl-2]center dot 2H(2)O (7) and [Bi(H2BzpOHPh)Cl-3]center dot 2H(2)O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl-(H2AcpClPh), -para-nitro-phenyl (H2AcpNO(2)Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh).Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4).The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts.Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO(2)Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer. (C) 2016 Elsevier Ltd. All rights reserved.
• Complexation of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones to copper(II) as an effective strategy for antimicrobial activity improvement
  作者：Angel A. Recio Despaigne、Fernanda B. Da Costa、Oscar E. Piro、Eduardo E. Castellano、Sonia R.W. Louro、Heloisa Beraldo

  DOI：10.1016/j.poly.2012.03.017

  日期：2012.5

  Complexes [Cu(2AcPh)Cl]center dot 2H(2)O (1), [Cu(2AcpClPh)Cl]center dot 2H(2)O (2), [Cu(2AcpNO(2)Ph)Cl] (3), [Cu(2BzPh)Cl] (4). [Cu(2BzpClPh)Cl] (5) and [Cu(2BzpNO(2)Ph)Cl] (6) were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph), 2-benzoylpyridine-phenylhydrazone (H2BzPh), 2-benzoylpyridine-para-chloro-phenylhydrazone (H2BzpClPh) and 2-benzoylpyridine-para-nitro-phenylhydrazone (H2BzpNO(2)Ph). The hydrazones showed poor antibacterial effect against Staphylococcus aureus, Enterococcus faecalis and Pseudomonas aeruginosa but demonstrated significant antifungal activity against Candida albicans. Upon coordination to copper(II) the antibacterial and antifungal activities appreciably increased. H2AcpClPh, H2BzpClPh and their copper(II) complexes (2) and (5), respectively, were as active as fluconazole against C. albicans. (C) 2012 Elsevier Ltd. All rights reserved.