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Design, Synthesis and Bioactivities of Novel 1,4-Pentadien-3-one Derivatives Containing a Substituted Pyrazolyl Moiety.

ABSTRACT: In this study, in order to find novel biologically active penta-1,4-dien-3-one derivatives, a series of penta-1,4-dien-3-one compounds containing a substituted pyrazole subunit were designed and synthesized. Their structures were characterized by ¹H-NMR, ¹³C-NMR and elemental analysis. The preliminary bioassays displayed that most of the title compounds showed significant antiproliferative activity against HepG2 cell lines. Especially, compounds 7a-m, o, r, s, u, w, y and z were active against HepG2 cells with IC₅₀ values of 0.10-5.05 ?M, which were superior to that of the contrast sorafenib (IC₅₀ = 16.20 ?M).

SUBMITTER: Chen C

PROVIDER: S-EPMC6152210 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Design, Synthesis and Bioactivities of Novel 1,4-Pentadien-3-one Derivatives Containing a Substituted Pyrazolyl Moiety.

Chen Cuili C Chen Jia J Gu Haiying H Bao Ning N Dai Hong H

Molecules (Basel, Switzerland) 20170706 7

In this study, in order to find novel biologically active penta-1,4-dien-3-one derivatives, a series of penta-1,4-dien-3-one compounds containing a substituted pyrazole subunit were designed and synthesized. Their structures were characterized by ¹H-NMR, 13C-NMR and elemental analysis. The preliminary bioassays displayed that most of the title compounds showed significant antiproliferative activity against HepG2 cell lines. Especially, compounds 7a-m, o, r, ...[more]

PMID: 28684715

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Project description:Objectives:The novel 1,5-diaryl-1,4-pentadien-3-one derivatives were studied for analgesic, anti-inflammatory and anticancer potential to establish their role in pain, inflammatory disorders and cancer. Materials and Methods:Two 1,5- diaryl-1,4-pentadien-3-one derivatives: (1E,4E)- 5-(4-fluoro phenyl)-1-(4-methoxyphenyl)- 2-methylpenta-1,4-dien-3-one (A2K2A17) and (1E,4E)-5-(4-nitrophenyl)-1-(4-nitrophenyl)-2-ethylhexa-1,4-dien-3-one (A11K3A11) were synthesized and characterized via 1H NMR and 13C NMR techniques. Molecular docking, anti-inflammatory, analgesic and anticancer activities were performed using Auto Doc Vina, carrageenan mediated paw edema and formalin induced chronic inflammation, acetic acid induced writhings and hotplate assay and brine-shrimp lethality assay. Results:A2K2A17 and A11K3A11 showed high computational affinities (binding energy > -9.0 Kcal/mol) against COX-1, kappa receptor and braf kinase domain. A2K2A17 and A11K3A11 exhibited moderate docking affinities (binding energy > -8.0 Kcal/mol) against COX-2, human capsaicin receptor, tumor necrosis factor, lipoxygenase, colony stimulating factor, delta receptor, cyclin dependent protein kinase-2, mitogen activated kinase, mu receptor and kit kinase domain. A2K2A17 and A11K3A11 possess low docking affinities (binding energy > -7.0 Kcal/mol) against purinoceptor, platelets-derived growth Factor-1 and vascular-endothelial growth factor. In analgesic activity, A2K2A17 (1-30 mg/kg) and A11K3A11 (1-10 mg/kg) decreased acetic acid induced writhes and prolonged the latency time (P<0.01, P<0.001 vs saline group) respectively. A2K2A17 (10-30 mg/kg) and A11K3A11 (1-10 mg/kg) reduced carrageenan as well as formalin mediated edema (P<0.01, P<0.001). A2K2A17 found effective for cytotoxicity assay with LC50 value 1.5 µg/ml. Conclusion:The in silico, in vitro and in vivo studies on A2K2A17 and A11K3A11 reports their computational binding affinities against targets as well as the analgesic, anti-inflammatory and the anticancer effects.

Dataset Information

Design, Synthesis and Bioactivities of Novel 1,4-Pentadien-3-one Derivatives Containing a Substituted Pyrazolyl Moiety.

Publications

Design, Synthesis and Bioactivities of Novel 1,4-Pentadien-3-one Derivatives Containing a Substituted Pyrazolyl Moiety.

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