2-benzoylpyridine-para-hydroxyphenylhydrazone | 541517-13-9

• 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-benzoylpyridine-para-hydroxyphenylhydrazone
• 英文别名: 4-hydroxy-N-[[phenyl(pyridin-2-yl)methylidene]amino]benzamide
• CAS: 541517-13-9
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: WCFHMHRJJORKRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bismuth(III) chloride 、 2-benzoylpyridine-para-hydroxyphenylhydrazone 以 甲醇 为溶剂， 反应 4.0h， 以58%的产率得到[2-benzoylpyridine-para-hydroxy-phenylhydrazone(trichloro)bismuth(III)]
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2016.05.007

文献信息

• Synthesis, structural and in-vitro functional studies of half-sandwich platinum group metal complexes having various bonding modes of benzhydrazone derivative ligands
  作者：Lathewdeipor Shadap、Jaya Lakshmi Tyagi、Krishna Mohan Poluri、Emma Pinder、Roger M. Phillips、Werner Kaminsky、Mohan Rao Kollipara

  DOI：10.1016/j.poly.2019.114293

  日期：2020.1

  while rhodium and iridium complexes exhibited N∩N bonding mode with the migration of the N H proton to the adjacent C O (keto) group forming enol. Anti-bacterial activity studies (against Gram-positive and Gram-negative bacteria) as well as anti-cancer [HCT116 p53 wild type (p53+/+) and HCT116 p53 null (p53−/−)] were carried out for all the complexes as well as ligands where interestingly, ligand L2

  摘要通过使金属前体[（芳烃）MCl2] 2（芳烃=对甲基异丙基苯，Cp *； M = Ru，Rh和Ir）与苯并zone衍生物配体L1，L2和L3反应合成了配合物1–9 PF6为抗衡离子的阳离子络合物的制备 钌配合物表现出N = O键合模式，而铑和铱配合物表现出N = N键合模式，其中NH质子迁移到相邻的CO（酮）基团形成烯醇。对所有复合物均进行了抗菌活性研究（针对革兰氏阳性和革兰氏阴性细菌）以及抗癌药[HCT116 p53野生型（p53 + / +）和HCT116 p53 null（p53-/-）]。有趣的是，配体L2和配合物5对两种生物学研究都显示出高活性（体外）。在Ru，Rh和Ir中，
• Synthesis, spectroscopic studies and crystal structures of two new vanadium complexes of 2-benzoylpyridine containing hydrazone ligands
  作者：Mini Kuriakose、M.R. Prathapachandra Kurup、E. Suresh

  DOI：10.1016/j.poly.2007.01.008

  日期：2007.7

  aroylhydrazones is studied. Oxovanadium(IV) and (V) complexes are obtained, indicating the binding of ligands to the metal ion through the imine nitrogen, enolate oxygen and pyridyl nitrogen. The oxovanadium(IV) compound [VOL1(OCH3)] · 0.14H2O (1a) gets oxidized to dioxovanadium(V) species [VO2L1] (1b) upon crystal formation. The crystal structures of the ligand and the two vanadium complexes are reported. Single

  摘要研究了VO（acac）2与2-苯甲酰基吡啶取代的芳酰基hydr的反应。获得了氧钒（IV）和（V）络合物，表明配体通过亚胺氮，烯醇氧和吡啶基氮与金属离子结合。氧钒（IV）化合物[VOL1（OCH3）]·0.14H2O（1a）在形成晶体时被氧化为二氧钒（V）物种[VO2L1]（1b）。报道了配体和两种钒配合物的晶体结构。化合物[VO（HL2）（μ2-O）] 2（2）的单晶X射线衍射研究显示出中心对称的二聚体。
• Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones
  作者：Elisa D.L. Piló、Angel A. Recio-Despaigne、Jeferson G. Da Silva、Isabella P. Ferreira、Jaqueline A. Takahashi、Heloisa Beraldo

  DOI：10.1016/j.poly.2015.05.004

  日期：2015.9

  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.
• 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.