Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells

Xia, Yong; Fan, Chuandong; Zhao, Bao‐Xiang; Zhao, Jing; Shin, Dong‐Soo; Jiang, Miao

doi:10.1016/j.ejmech.2008.01.021

Cited by 182 publications

(49 citation statements)

References 19 publications

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“…In our laboratory, several pyrazole derivatives have been synthesized. We found that 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives could suppress A549 lung cancer cell growth [3] , 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives induced A549 cell autophagy [4] and ethyl 3-(o-chlorophenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate inhibited human umbilical vein endothelial cell (HUVEC) apoptosis [5] . Nevertheless, no reports about the effects of In our previous papers, we synthesized a series of pyrazole derivatives and obtained their crystal structures [6][7][8][9] .…”

Section: Introductionmentioning

confidence: 99%

N-benzyl-5-phenyl-1H-pyrazole-3-carboxamide promotes vascular endothelial cell angiogenesis and migration in the absence of serum and FGF-2

Zhang

Huang

et al. 2011

Acta Pharmacol Sin

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Aim: To investigate the effect of N-benzyl-5-phenyl-1H-pyrazole-3-carboxamide (BPC) on angiogenesis in human umbilical vein endothelial cells (HUVECs).Methods: Capillary-like tube formation on matrigel and cell migration analyses were performed in the absence of serum and fibroblast growth factor (FGF-2). Reactive oxygen species (ROS) were measured using a fluorescent probe, 2', 7'-dichlorodihydrofluorescein (DCHF). The nitric oxide (NO) production of HUVECs was examined using a NO detection kit. Morphological observation under a phase contrast microscope, a viability assay using 3-[4, 5-dimethylthiazol-2-yl]-2, 5-diphenyl-tetrazolium (MTT) and a lactate dehydrogenase (LDH) activity analysis by a detection kit were performed to evaluate the toxicity of BPC on HUVECs in the presence of serum and FGF-2. The level of hypoxia-inducible factor 1α (HIF-1α) and the release of vascular endothelial growth factor (VEGF) were measured by Western blot and ELISA, respectively. Results: In the absence of serum and FGF-2, cells treated with BPC (5-20 μmol/L) rapidly aligned with one another and formed tubelike structures within 12 h. In the presence of serum and FGF-2, cells treated with BPC for 24, 48 and 72 h had no changes in morphology, viability or LDH release compared with the control group. Cell migration in the BPC-treated group was significantly increased compared with the control group. During this process, NO production and ROS level were elevated dramatically, and the levels of HIF-1α and VEGF were increased dependent on the generation of ROS. Conclusion: BPC most effectively promoted angiogenesis and migration in HUVECs in the absence of FGF-2 and serum.

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Section: Introductionmentioning

confidence: 99%

N-benzyl-5-phenyl-1H-pyrazole-3-carboxamide promotes vascular endothelial cell angiogenesis and migration in the absence of serum and FGF-2

Zhang

Huang

et al. 2011

Acta Pharmacol Sin

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“…Hydrazone derivatives of isoniazid and other hydrazides have been reported to exhibit marked antimicrobial activity (10)(11)(12)(13)(14). Furthermore, a number of substituted hydrazone derivatives have been synthesized and evaluated for their antitumor activity, with certain promising results having been reported (15)(16)(17).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and anticancer activities of transition metal complexes with a nicotinohydrazone ligand

et al. 2017

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Abstract. The reaction of divalent transition metal salts and (E)-N'-(1-(pyridin-2-yl)ethylidene)nicotinohydrazide (penh) led to the formation of [Mn(penh) 2 ] (complex 1), [Co(penh) 2 ] (complex 2), [Cu(penh) 2 ] (complex 3) and [Cd (penh) 2 ] (complex 4) complexes. The four complexes were characterized using elemental analyses, infrared spectra and single-crystal X-ray diffraction analyses. Subsequently, the complexes were used for in vitro cell level experiments to determine potential antitumor effects. The results demonstrated that the complexes exhibited a similar structure; however, they were crystallized with distinct space groups. In comparison with the uncomplexed penh ligand, all four complexes were able to markedly decrease the proliferation rate of various types of tumor cell, including the human lung cancer cell line A549, human gastric cancer cell line BGC823 and human esophageal cancer cell line Eca109, in a concentration-dependent manner. Furthermore, the complexes promoted tumor cell apoptosis, as demonstrated in the apoptosis assay, and this was confirmed using electrophoresis. IntroductionHydrazide-hydrazone derivatives are an important class of biologically active molecules, which have attracted the attention of medicinal chemists due to their wide-ranging pharmacological properties and their potential application as antitumor, antineoplastic, antiviral and anti-inflammatory agents (1-6).In particular, aroylhydrazone complexes of transition metals are known to provide useful models for the elucidation of the underlying molecular mechanism of enzyme inhibition by hydrazine derivatives (7) and for their potential pharmacological application (8,9). Hydrazone derivatives of isoniazid and other hydrazides have been reported to exhibit marked antimicrobial activity (10-14). Furthermore, a number of substituted hydrazone derivatives have been synthesized and evaluated for their antitumor activity, with certain promising results having been reported (15-17).The aim of the present study was to develop potent anticancer agents. (E)-N'-(1-(pyridin-2-yl)ethylidene) nicotinohydrazide (penh), and [Mn(penh) 2 ] (complex 1), [Co (penh) 2 ] (complex 2), [Cu(penh) 2 ] (complex 3) and [Cd(penh) 2 ] (complex 4) metal complexes were synthesized, and their cytotoxicity against human lung cancer (A549), human gastric cancer (BGC823) and human esophageal cancer (Eca109) cell lines was investigated. Materials and methodsMaterials. All starting materials were obtained commercially and used as received. The A549 human lung cancer, BGC823 human gastric cancer and Eca109 human esophageal cancer cell lines were obtained from the Cell Culture Center of the Basic Institute of Medical Sciences (Peking Union Medical College, Beijing, China). Cell culture reagents were purchased from Gibco (Thermo Fisher Scientific, Inc., Waltham, MA, USA). An Annexin V/propidium iodide (PI) double staining kit was purchased from BD Biosciences (Franklin Lakes, NJ, USA). MTT and dimethyl sulfoxide (DMSO) were purchased from Sigma-Aldrich (Merc...

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“…Among the reported studies, 4-quinolinylpyrazoles, 4-quinolinylimidazoles, 4-quinoxalinylpyrazoles and 4-( [1,2,4]triazolo [1,5-a]pyridin-6-yl)pyrazoles showed promising antiproliferative properties by inhibiting transforming growth factor-b type 1 receptor kinase, also known as activin receptor-like kinase 5 (ALK5) [12e15]. Moreover, pyrazole-5-carboxylate [10,16], pyrazole-5-carboxamide [4] and pyrazole-5-carbohydrazide [6,8,9,11] derivatives were also shown to have a significant anticancer activity against A549 lung cancer cell lines by inducing apoptosis or autophagy. Therefore, a wide range of information provided in the literature presents an ample opportunity for further investigation of pyrazole derivatives for the discovery of novel anticancer therapeutics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and preliminary mechanistic evaluation of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid amides with potent antiproliferative activity on human cancer cell lines

Pirol

Çalışkan

Durmaz

et al. 2014

European Journal of Medicinal Chemistry

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a b s t r a c tWe synthesized a series of novel amide derivatives of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid and assessed their antiproliferative activities against three human cancer cell lines (Huh7, human liver; MCF7, breast and HCT116, colon carcinoma cell lines) with the sulforhodamine B assay. Compound 4j with 2-chloro-4-pyridinyl group in the amide part exhibited promising cytotoxic activity against all cell lines with IC 50 values of 1.6 mM, 3.3 mM and 1.1 mM for Huh7, MCF7 and HCT116 cells, respectively, and produced dramatic cell cycle arrest at SubG1/G1 phase as an indicator of apoptotic cell death induction. On the basis of their high potency in cellular environment, these straightforward pyrazole-3-carboxamide derivatives may possess potential in the design of more potent compounds for intervention with cancer cell proliferation.

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Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells

Cited by 182 publications

References 19 publications

N-benzyl-5-phenyl-1H-pyrazole-3-carboxamide promotes vascular endothelial cell angiogenesis and migration in the absence of serum and FGF-2

N-benzyl-5-phenyl-1H-pyrazole-3-carboxamide promotes vascular endothelial cell angiogenesis and migration in the absence of serum and FGF-2

Synthesis, characterization and anticancer activities of transition metal complexes with a nicotinohydrazone ligand

Synthesis and preliminary mechanistic evaluation of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid amides with potent antiproliferative activity on human cancer cell lines

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