- Discovery of heterocyclic substituted dihydropyrazoles as potent anticancer agents
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In this work, a series of novel heterocyclic substituted dihydropyrazole derivatives have been prepared, and in vitro anticancer activity against a panel of human tumor cell lines by SRB were evaluated. The results indicated that piperazine substituted dihydropyrazole derivatives exhibited superior anticancer activity than that of other compounds. Especially, compounds 4g, 4h, 4l, 4m, 4o, 6g, 6j and 6l showed potent antitumor activity. Further mechanism study demonstrated that compound 4o could induce G2/M arrest in HCC1806 cell and p21 accumulation significantly.
- Chen, Chuan-Huizi,Jiang, Yuan,Wu, Runfang,Tang, Yanling,Wan, Chunping,Gao, Hui,Mao, Zewei
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- Synthesis and biological evaluation of novel hybrid compounds between chalcone and piperazine as potential antitumor agents
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Chalcones play an important role in living organisms with a wide range of biological activities including potent antitumor activity. Previously, we reported that N-aryl piperazine compounds have excellent biological activity. To further explore the struct
- Mao, Zewei,Zheng, Xi,Qi, Yan,Zhang, Mengdi,Huang, Yao,Wan, Chunping,Rao, Gaoxiong
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- Conversion of iodine to fluorine-18 based on iodinated chalcone and evaluation for β-amyloid PET imaging
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In the amyloid cascade hypothesis, β-amyloid (Aβ) plaques is one of the major pathological biomarkers in the Alzheimer's disease (AD) brain. We report the synthesis and evaluation of novel radiofluorinated chalcones, [18F]4-dimethylamino-4′-flu
- Kaide, Sho,Ono, Masahiro,Watanabe, Hiroyuki,Shimizu, Yoichi,Nakamoto, Yuji,Togashi, Kaori,Yamaguchi, Aiko,Hanaoka, Hirofumi,Saji, Hideo
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- A highly selective fluorescent chemosensor for cyanide anions based on a chalcone derivative in the presence of iron(III) ions, and its capacity for living cell imaging in mixed aqueous systems
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A chalcone, 4-dimethylamino 4-fluorochalcone (1) with donor-acceptor structure characteristics is found to exhibit a distinct green fluorescence and good stability in CH3CN/water (v/v = 1: 9) buffer solution (Tris-HCl, pH = 7.4), and the in sit
- Yang, Wen,Cheng, Zhongqin,Xu, Yunlong,Shao, Jie,Zhou, Weiqun,Xie, Juan,Li, Mengying
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Read Online
- Pyrazoline analogs as potential anticancer agents and their apoptosis, molecular docking, MD simulation, DNA binding and antioxidant studies
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N-formyl pyrazoline derivatives (3a–3l) were designed and synthesized via Michael addition reaction through cyclization of chalcones with hydrazine hydrate in presence of formic acid. The structural elucidation of N-formyl pyrazoline derivatives was carri
- Rana, Manish,Arif, Rizwan,Khan, Faez Iqbal,Maurya, Vikas,Singh, Raja,Faizan, Md Imam,Yasmeen, Shama,Dar, Sajad Hussain,Alam, Raquib,Sahu, Ankita,Ahmad, Tanveer,Rahisuddin
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- Synthesis, biological activities, and docking study of novel chalcone-pleuromutilin derivatives
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The issue of antibiotic resistance is becoming progressively serious these days, and the feasible solution to address it is to develop and discover novel antibiotics. The diterpene natural pleuromutilin is a prominent candidate for its special mode of act
- Xie, Chuan,Zhang, Siyu,Zhang, Wei,Wu, Chunxia,Yong, Can,Sun, Yuhao,Zeng, Zhengxing,Zhang, Qian,Huang, Zixin,Chen, Tian,Zhang, Yuanyuan
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p. 836 - 849
(2020/04/30)
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- Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models
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A series of new pyrimidine–triazine hybrids (4a–t) was designed and synthesized, from which potent anticonvulsant agents were identified. Most of the compounds exhibited promising anticonvulsant activity against the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests, along with minimal motor impairment with higher safety compared to the standard drugs, phenytoin and carbamazepine. In the series, 5-(4-(4-fluorophenyl)-6-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4o) and 5-(6-(4-hydroxy-3-methoxyphenyl)-4-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4s) emerged as most potent anticonvulsant agents with median doses of 22.54 and 29.40 mg/kg (MES ED50), 285.02 and 293.42 mg/kg (scPTZ ED50), and 389.11 and 412.16 mg/kg (TD50), respectively. Docking studies were also performed for all synthesized compounds to get insight into the binding pattern toward the GABAA receptor as a possible mechanism of their anticonvulsant action, and in silico ADME studies were carried out to predict the safety and stability of the molecules. The increased GABA level in the experimental animals in the neurochemical estimation assay confirmed their GABAergic modulating activity. The most potent compounds were also evaluated for their neurotoxic and hepatotoxic effects. Fortunately, they did not show any sign of neurotoxicity or hepatotoxicity, suggesting that they have a broad spectrum of anticonvulsant activity with a large safety margin. Together, this research suggested that 4o and 4s may serve as leads in the discovery and development of new anticonvulsant drugs.
- Sahu, Meeta,Siddiqui, Nadeem,Naim, Mohd. Javed,Alam, Ozair,Yar, Mohammad Shahar,Sharma, Vidushi,Wakode, Sharad
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- Concise synthesis and biological evaluation of chalcone derivatives bearing n-heterocyclic moieties
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In this study, we designed and synthesized a series of chalcone derivatives bearing N-heterocyclic moieties, and screened in vitro antiinflammatory in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and anticancer activity against a panel of hum
- Mao, Zewei,Zheng, Xi,Lin, Yuping,Qi, Yan,Hu, Chunyan,Wan, Chunping,Rao, Gaoxiong
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p. 1102 - 1110
(2016/07/06)
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- Synthesis, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones
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In the present study a series of novel pyrazolines derivatives has been synthesized, and their structures assigned on the basis of FT-Raman, 1H and 13C NMR spectral data and computational DFT calculations. A joint computational study using B3LYP/6-311G(2d,2p) density functional theory and FT-Raman investigation on the tautomerism of 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carbothioamide and 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carboxamide are presented. The structures were characterized as a minimum in the potential energy surface using DFT. The calculated Raman and NMR spectra were of such remarkable agreement to the experimental results that the equilibrium between tautomeric forms has been discussed in detail. Our study suggests the existence of tautomers, the carboxamide/carbothioamide group may tautomerize, in the solid state or in solution. Thermodynamic data calculated suggests that the R(CS)NH2 and R(CO)NH2 species are more stable than the R(CNH)SH and R(CNH)OH species. Additionally, results found for the 1H NMR shifting, pointed out to which structure is present.
- Miguel, Fbio Balbino,Dantas, Juliana Arantes,Amorim, Stefany,Andrade, Gustavo F.S.,Costa, Luiz Antnio Sodr,Couri, Mara Rubia Costa
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supporting information
p. 318 - 326
(2015/08/06)
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- Characterization of the Fluorescence Properties of 4-Dialkylaminochalcones and Investigation of the Cytotoxic Mechanism of Chalcones
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Understanding the mechanisms responsible for the various biological activities of chalcones, particularly the direct cellular targets, presents an unmet challenge. Here, we prepared a series of fluorescent chalcone derivatives as chemical probes for their
- Zhou, Bo,Jiang, Peixin,Lu, Junxuan,Xing, Chengguo
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p. 539 - 552
(2016/08/26)
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- Synthesis, analgesic and anti-inflammatory activities of chalconyl-incorporated hydrazone derivatives of mefenamic acid
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A series of chalconyl-incorporated hydrazone derivatives of mefenamic acid was synthesized in order to obtain new compounds with potential analgesic and anti-inflammatory activity having lesser side effects. The structures of all synthesized compounds were confirmed by means of elemental analysis, IR, 1H NMR, 13C NMR and mass spectra. All compounds were evaluated for their analgesic and anti-inflammatory activities by tail-flick method and carrageenan-induced rat paw edema test, respectively. Among all the synthesized compounds, compounds (4a) and (4j) exhibited the most prominent and consistent anti-inflammatory activity. In acute ulcerogenicity study, it can be concluded that compounds (4a) and (4j) are devoid of the deadlier gastrointestinal toxicities.
- Kumar, Neeraj,Chauhan, Lalit Singh,Sharma, Chandra Shekhar,Dashora, Nipun,Bera, Rajendra
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p. 2580 - 2590
(2015/02/05)
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- Palladium-catalyzed decarboxylative arylation of benzoylacrylic acids toward the synthesis of chalcones
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It has been found that readily available 3-benzoylacrylic acids undergo palladium-catalyzed decarboxylative arylation with arylboronic acids in the presence of a copper salt oxidant to produce chalcone derivatives. The decarboxylative arylation could also be achieved using aryl halides as the alternative aryl source to expand the applicable scope.
- Unoh, Yuto,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 5096 - 5102
(2013/07/05)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE
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There is provided a composition comprising a compound represented by general formula (I), wherein R1 represents a 5-iodothiophen-2-yl group or the like, and R2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.
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Page/Page column 40; 58
(2009/04/23)
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- Fluoro-pegylated chalcones as positron emission tomography probes for in vivo imaging of β-amyloid plaques in Alzheimer's disease
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This paper describes the synthesis and biological evaluation of fluoro-pegylated (FPEG) chalcones for the imaging of β-amyloid (Aβ) plaques in patients with Alzheimer's disease (AD). FPEG chalcone derivatives were prepared by the aldol condensation reacti
- Ono, Masahiro,Watanabe, Rumi,Kawashima, Hidekazu,Yan, Cheng,Kimura, Hiroyuki,Watanabe, Hiroyuki,Haratake, Mamoru,Saji, Hideo,Nakayama, Morio
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experimental part
p. 6394 - 6401
(2010/03/31)
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- Synthesis and anti-inflammatory activity of fluorinated phenyl styryl ketones and N-phenyl-5-substituted aryl-3-p-(fluorophenyl) pyrazolins and pyrazoles
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Various N-phenyl-5-substituted aryl-3-p-(fluorophenyl) pyrazolins and pyrazoles were synthesized by cyclization of the corresponding 4- (fluorophenyl) styryl and 4-(fluorophenyl) dibromostyryl ketones. These compounds were characterized by elemental analy
- Nargund,Hariprasad,Reddy
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p. 892 - 894
(2007/10/02)
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- Preparation and Reactions of Some New Fluorinated Keto-stabilised Arsonium Ylides
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Zwei neue fluorierte ketostabilisierte Triphenylarsoniumsalze 2a, b werden dargestellt, die bei der alkalischen Zersetzung die entsprechenden neuen Arsoniumylide 3a, b ergeben.Bei Zugabe von Perchlorsaeure entstehen daraus die Perchlorate 4a, b.Bei der Re
- Bansal, Raj K.,Bhagchandani, Gope
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- Polarographic Investigations on α,β-Unsaturated Ketones: 1-(4'-Fluorophenyl)-3-phenyl-2-propenones
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The reduction of various substituted 1-(4'-fluorophenyl)-3-phenyl-2-propenones at the dropping mercury electrode has been examined.In 50percent ethanol-water buffered media fluorochalkones give two well-defined waves in acid media and three waves in neutral and alkaline media.The one-electron electroreduction in the first two steps results in the formation of dihydrochalcone, which subsequently gets further reduced to the secondary alcohol.A large variety of substituents on the benzylidene moiety of 1-(4'-fluorophenyl)-3-phenyl-2-propenone, affect the half-wave potentials according to the relation E1/2 = a + b.Substituents with a positive ? value render the reduction easier and shift the E1/2 to more positive values, whereas groups with negative ? values make the electroreduction more difficult, resulting in more negative E1/2 compared to the parent compound.A comparison of the E1/2 values of o- and p-chloro substituted 1-(4'-fluorophenyl)-3-phenyl-2-propenones shows that o-substituted derivative undergoes reduction at a more positive potential indicating a positive ortho effect for this system.
- Katiyar, Sarvagya S.,Latithambica, M.
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p. 956 - 960
(2007/10/02)
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