2-benzoylpyridine-para-chloro-phenylhydrazone | 544461-79-2

• 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-benzoylpyridine-para-chloro-phenylhydrazone
• 英文别名: 2-benzoylpyridine-para-chlorophenylhydrazone；H2BzpClPh；4-chloro-N-[[phenyl(pyridin-2-yl)methylidene]amino]benzamide
• CAS: 544461-79-2
• 化学式: C₁₉H₁₄ClN₃O
• 分子量: 335.793
• InChiKey: AVWJYKZWNKXEPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoylpyridine-para-chloro-phenylhydrazone 、 三氯化锑 以 甲醇 为溶剂， 反应 4.0h， 以42%的产率得到[2-benzoylpyridine-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-苯甲酰吡啶 、 4-氯苯甲酰肼 以 甲醇 为溶剂， 生成 2-benzoylpyridine-para-chloro-phenylhydrazone
  参考文献：
  名称：

  衍生自2-苯甲酰基吡啶的席夫碱的一些新的二/三-有机锡（IV）配合物的合成，光谱研究和体外抗菌活性

  摘要：

  在本工作中，通过2-苯甲酰基吡啶席夫碱与R2SnCl2，R3SnCl（R = Me，n -Bu或Ph）的缩合反应合成了一系列二十四种[R2SnClL，R3SnL]型有机锡（IV）配合物。以1：1的摩尔比。这些配合物通过IR，1H-和13C-，119Sn-NMR，XRD和质谱技术进行了很好的表征。在寻找生物学上更有效的抗菌剂时，通过连续稀释法评估了所有合成的配体和有机锡复合物对两种革兰氏阳性和两种革兰氏阴性细菌以及两种真菌菌株的体外抗菌活性。光谱数据的结果表明，形成的配合物与三齿配体六配位，三配体通过偶氮甲碱N，吡啶N和羧酸酯O的连接位点进行配位。与锡金属配位的配体显示出明显的杀生物活性增强。但是，Ph和Bu配合物更令人陶醉。结果显示，与革兰氏阴性菌株相比，合成的复合物对革兰氏阳性菌株更具毒性，这可能归因于脂多糖外脂质膜的存在。

  DOI：

  10.2298/jsc160429089k

文献信息

• 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.
• Structural studies on zinc(II) complexes with 2-benzoylpyridine-derived hydrazones
  作者：Angel A. Recio Despaigne、Jeferson G. Da Silva、Ana Cerúlia M. do Carmo、Oscar E. Piro、Eduardo E. Castellano、Heloisa Beraldo

  DOI：10.1016/j.ica.2008.09.040

  日期：2009.5

  2-Benzoylpyridine-phenylhydrazone (H2BzPh), 2-benzoylpyridine-para-chloro-phenylhydrazone (H2BzpClPh), and 2-benzoylpyridine-para-nitro-phenyl (H2BzpNO(2)Ph) hydrazone were obtained and fully characterized, as well as their zinc(II) complexes [Zn(H2BzPh)Cl-2] (1), [Zn(H2BzClPh)Cl-2] (2) and [Zn(H2BzpNO(2)Ph)Cl-2] (3). During the syntheses of complex 1 a second product crystallized, which was characterized as [Zn(2BzPh)(2)] (1a). Upon re-crystallization in 1: 9 DMSO: acetone conversion of 2 into [Zn(H2BzpClPh)Cl2] center dot H2O (2a) and of 3 into [Zn(2BzpNO(2)Ph)Cl(DMSO)] (3a) occurred. The crystal structures of 1a, 2a and 3a were determined. In 1a the two nearly perpendicular H2BzPh ligands give rise to a distorted octahedral environment around the metal. The 5-fold coordination around the metal is completed with two chloride ions in 2a and with one chloride and one oxygen atom from DMSO in 3a. (c) 2008 Elsevier B.V. All rights reserved.
• Synthesis, spectral studies and in vitro antimicrobial activity of some new di/tri-organotin (IV) complexes of Schiff bases derived from 2-benzoylpyridine
  作者：Priyanka Khatkar、Sonika Asija、Namita Singh

  DOI：10.2298/jsc160429089k

  日期：——

  of 2-benzoylpyridine Schiff bases with R2SnCl2, R3SnCl (R = Me, n -Bu or Ph) in 1:1 mole ratio. These complexes were well characterized by IR, 1H-, and 13C-, 119Sn-NMR, XRD and mass spectral techniques. In the search for biologically more effective antimicrobial agents, all the synthesized ligands and organotin complexes were evaluated for their in vitro antimicrobial activities against two Gram-positive

  在本工作中，通过2-苯甲酰基吡啶席夫碱与R2SnCl2，R3SnCl（R = Me，n -Bu或Ph）的缩合反应合成了一系列二十四种[R2SnClL，R3SnL]型有机锡（IV）配合物。以1：1的摩尔比。这些配合物通过IR，1H-和13C-，119Sn-NMR，XRD和质谱技术进行了很好的表征。在寻找生物学上更有效的抗菌剂时，通过连续稀释法评估了所有合成的配体和有机锡复合物对两种革兰氏阳性和两种革兰氏阴性细菌以及两种真菌菌株的体外抗菌活性。光谱数据的结果表明，形成的配合物与三齿配体六配位，三配体通过偶氮甲碱N，吡啶N和羧酸酯O的连接位点进行配位。与锡金属配位的配体显示出明显的杀生物活性增强。但是，Ph和Bu配合物更令人陶醉。结果显示，与革兰氏阴性菌株相比，合成的复合物对革兰氏阳性菌株更具毒性，这可能归因于脂多糖外脂质膜的存在。
• 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.