- Synthesis, antioxidant and anticholinesterase activities of novel quinoline-aminophosphonate derivatives
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A series of 20 novel α-aminophosphonate derivatives bearing quinoline or quinolone moiety was designed and synthesized via Kabachnik-Fields reaction in the presence of triethylammonium acetate as a solvent and catalyst under ultrasound irradiation. This procedure affords products in high yields and short reaction times. Molecular structures of the synthesized compounds 4a-g and 5a-m were confirmed using various spectroscopic methods. The antioxidant activity of these compounds was evaluated by eight complementary in vitro tests. The anticholinesterase activity (AChE, BChE) of these compounds were also evaluated. In addition, theoretical calculations of all compounds were investigated as corrosion inhibitors using density functional theory (DFT). The results revealed that 16 of these compounds exhibited high levels of antioxidant activities depending on the assay and that most compounds showed more potent inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).
- Bazine, Ismahene,Bensegueni, Rafik,Bensouici, Chawki,Boukhari, Abbes,Cheraiet, Zinelaabidine
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- Synthesis, photophysical properties and theoretical studies of new bis-quinolin curcuminoid BF2-complexes and their decomplexed derivatives
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This paper presents the synthesis and characterization of two series of new bis-quinolin curcuminoid BF2-complexes 11 and their respective decomplexed bis-quinolin curcuminoid derivatives 12, in an attempt to understand their optical properties. The synthesized compounds showed interesting fluorescent characteristics in both solution and in solid-state. The characteristic of the electronic transitions involved in these systems were measured via Uv-vis spectroscopy and fluorescence spectroscopy. Results revealed that the absorption and emission bands are dependent of the structure of compounds 11 and 12 but also of the type of substituent, even showing a push-pull behavior in those derivatives substituted with methyl group. These findings were also confirmed through computational calculations at DFT level via simulations of the Uv-vis spectra and determining the topology of the border orbitals responsible for light absorption.
- Abonia, Rodrigo,Cabrera, Lorena,Insuasty, Braulio,Insuasty, Daniel,Ortiz, Alejandro,Quiroga, Jairo
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- An efficient one-pot synthesis, structure, antimicrobial and antioxidant investigations of some novel quinolyldibenzo[b,e][1,4]diazepinones
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A highly improved one-pot procedure for the synthesis of diazepinones, which incorporate a bioactive quinoline nucleus, under catalyst-, and solvent-free environment has been developed. The method allowed us to achieve the products in high yields without requiring a chromatographic separation. All new quinolyldibenzo[b,e][1,4]diazepinones 6a-h thus obtained were further treated to achieve N10-allylated products 7a-h by a simple allylation. The structure of all new synthesized compounds was established based on elemental analysis, mass, 1H NMR, 13C NMR, IR spectral data, 2D NMR experiments, and single crystal X-ray study. From in vitro antimicrobial activity studies it revealed all are active against Gram positive (Streptococcus pneumoniae, Clostridium tetani, and Bacillus subtilis), Gram negative (Salmonella typhi, Vibrio chlolerae and Escherichia coli), M. Tuberculosis H37RV bacteria, and fungus like Candia albicans and Aspergillus fumigatus. All were also found to display good antioxidant activity of a ferric reducing power.
- Parmar, Narsidas J.,Barad, Hitesh A.,Pansuriya, Bhavesh R.,Teraiya, Shashikant B.,Gupta, Vivek K.,Kant, Rajni
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- Microwave-assisted synthesis of diversely substituted quinoline-based dihydropyridopyrimidine and dihydropyrazolopyridine hybrids
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An efficient, catalyst-free, and one-pot three-component procedure for the synthesis of novel and nitrogen rich dihydropyrido[2, 3-d]pyrimidines and dihydro-1H-pyrazolo[3, 4-b]pyridines bearing a quinoline pharmacophore fragment is provided. Reactions proceeded in DMF under microwave irradiation of three-component mixtures of formyl-quinoline derivatives, primary heterocyclic amines and cyclic 1, 3-diketones. Interestingly, when conventional heating at reflux was used for the starting 5-amino-1-phenylpyrazole, the corresponding aromatized pyrazolopyridines were obtained as the main products. Single crystal X-ray analysis confirmed unequivocally the structure of both the dihydro- and aromatized products.
- Insuasty, Daniel,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Laali, Kenneth K.,Nogueras, Manuel,Cobo, Justo
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- A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents
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Novel tetrahydro-5H-benzo[e][1,4]diazepin-5-ones, several of them, containing the quinoline pharmacophore, were synthesized via a Schmidt rearrangement from their corresponding 1,2,3,4-tetrahydro-4-quinolones mediated by the NaN3/H2SO4 reaction conditions. Twelve of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where compound 24a presented a remarkable activity against 58 of the 60 cancer cell lines, with the most important GI50 values ranging from 0.047 to 8.16 μM and LC50 values ranging from 9.4 to > 100 μM. Additionally, some of them were evaluated as antimalarial, antitrypanosomal and antileishmanial agents. The best antimalarial response was observed for compound 22g with an EC50 = 13.61 μg/mL for Plasmodium falciparum, while compound 24d exhibited high activity against Trypanosoma cruzi. and Leishmania (V) panamensis with EC50 = 2.78 μg/mL and 3.35 μg/mL respectively.
- Insuasty, Daniel,Robledo, Sara M.,Vélez, Iván D.,Cuervo, Paola,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Abonia, Rodrigo
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- Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones
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Fifteen 2-quinolone thiosemicarbazone derivatives of which eleven were new, were synthesized at room temperature. The key intermediate was the quinolone carbaldehyde, from which thiosemicarbazones were formed by the reaction of thiosemicarbazides with the aldehyde moiety. The structures of the synthesized compounds were elucidated by 1D and 2D-NMR spectroscopy and mass spectrometry. The synthesized compounds showed antibacterial activity with MBCs in the range 0.80 to 36.49 mM against Staphylococcus aureus, Staphylococcus aureus Rosenbach (MRSA), Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Salmonella typhimurium. The best activity was seen when a larger halogen such as chlorine and bromine were substituted at C-6 on the quinolone scaffold and when a planar phenyl group was present on the thiosemicarbazone moiety. Activity was reduced when a smaller fluorine atom was present at C-6 or when a methyl group was attached to the thiosemicarbazone. This group of compounds showed a high negative binding affinity, which suggested promising antimcrobial activity. The 6-chloro derivative with a phenyl group on the thiosemicarbazone had the greatest negative binding affinity.
- Govender, Hogantharanni,Mocktar, Chunderika,Kumalo, Hezekiel M.,Koorbanally, Neil A.
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- Three novel transition metal complexes of 6-methyl-2-oxo-quinoline-3-carbaldehyde thiosemicarbazone: synthesis, crystal structure, cytotoxicity, and mechanism of action
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Three novel 6-methyl-2-oxo-quinoline-3-carbaldehyde thiosemicarbazone (H-L) transition metal complexes, [Cu(H-L)NO3H2O]·NO3 (1), [Zn(H-L)NO3H2O]·NO3 (2) and [CoL2] (3), were synthesized. In vitro antitumor screening revealed that complex 1 exhibited better inhibitory activities than the commercial anticancer drug cisplatin against SK-OV-3 and MGC80-3 tumor cell lines, with IC50 values of 10.35 ± 1.26 μM and 10.17 ± 0.95 μM, respectively. All three complexes showed low cytotoxicity toward the normal human liver HL-7702 cells compared with cisplatin. Their binding properties to DNA were investigated by various methods. It was found that the complexes interacted with DNA mainly through intercalation, and their binding affinities ranked in the order of 3 > 1 > 2. Complex 1 induced the highest apoptosis rate of MGC80-3 cells, and it caused cell arrest in the S phase according to flow cytometry. Further experiments confirmed that complex 1 triggered MGC80-3 cells apoptosis via a mitochondrial dysfunction pathway.
- Zou, Bi-Qun,Lu, Xing,Qin, Qi-Pin,Bai, Yu-Xia,Zhang, Ye,Wang, Meng,Liu, Yan-Cheng,Chen, Zhen-Feng,Liang, Hong
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- Design and synthesis of biquinolone-isoniazid hybrids as a new class of antitubercular and antimicrobial agents
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Twenty four biquinolone-isoniazid hybrids were designed based on molecular hybridization technique and synthesized via multicomponent cyclocondensation (MCC) approach. All the newly synthesized compounds were screened for their antimicrobial and antituber
- Jardosh, Hardik H.,Patel, Manish P.
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- Design, synthesis and pharmacological evaluation of new 3-(1H-benzimidazol-2-yl)quinolin-2(1H)-one derivatives as potential antitumor agents
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A series of new 3-(1H-benzimidazol-2-yl)quinolin-2(1H)-one derivatives (5a1?5d6) were designed and synthesized as antitumor agents. In vitro antitumor assay results showed that some compounds exhibited moderate to high inhibitory activity against HepG2, SK-OV-3, NCI-H460 and BEL-7404 tumor cell lines, and most compounds exhibited much lower cytotoxicity against the HL-7702 normal cell line compared to 5-FU and cisplatin. In vivo antitumor assay results demonstrated that 5a3 exhibited effective inhibition on tumor growth in the NCI-H460 xenograft mouse model and that 5d3 displayed excellent antiproliferative activity in the BEL-7402 xenograft model. These results suggested that both 5a3 and 5d3 could be used as anticancer drug candidates. Mechanistic studies suggested that compounds 5a3 and 5d3 exerted their antitumor activity by up-regulation of Bax, intracellular Ca2+ release, ROS generation, downregulation of Bcl-2, activation of caspase-9 and caspase-3 and subsequent cleavage of PARP, inhibition of CDK activity and activation of the p53 protein.
- Kuang, Wen-Bin,Huang, Ri-Zhen,Qin, Jiao-Lan,Lu, Xing,Qin, Qi-Pin,Zou, Bi-Qun,Chen, Zhen-Feng,Liang, Hong,Zhang, Ye
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- Microwave Synthesis of Fused Pyrans by Humic Acid Supported Ionic Liquid Catalyst and Their Antimicrobial, Antioxidant, Toxicity Assessment, and Molecular Docking Studies
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A series of fused quinolinyl and quinolonyl pyrans were synthesized via a one-pot reaction of quinolinyl and quinolonyl carbaldehydes, malononitrile, and a 1,3-diketone. The reactions were catalyzed by a new humic acid supported 1-butyl-3-methyl imidazoli
- Thangaraj, Muthu,Ranjan, Bibhuti,Muthusamy, Ramesh,Murugesan, Arul,Gengan, Robert Moonsamy
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- Preparation of Rhodium(III) complexes with 2(1H)-quinolinone derivatives and evaluation of their in vitro and in vivo antitumor activity
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A series of 2(1H)-quinolinone derivatives and their rhodium (III) complexes were designed and synthesized. All the rhodium (III) complexes exhibited higher in vitro cytotoxicity for Hep G2, HeLa 229, MGC80-3, and NCI-H460 human tumor cell lines than their ligands and cisplatin, and among them complex 9 was found to be selectively cytotoxic to tumor cells. Further investigation revealed that complex 9 caused cell cycle arrest at the G2/M phase and induced apoptosis, and inhibited the proliferation of Hep G2 cells by impeding the phosphorylation of epidermal growth factor receptor (EGFR) and its downstream enzymes. Complex 9 also up-regulated the proapoptotic proteins Bak, Bax, and Bim, which altogether activated caspase-3/9 to initiate cell apoptosis. Notably, complex 9 effectively inhibited tumor growth in the NCI-H460 xenograft mouse model with less adverse effect than cisplatin.
- Lu, Xing,Wu, Yi-Ming,Yang, Jing-Mei,Ma, Feng-E.,Li, Liang-Ping,Chen, Sheng,Zhang, Ye,Ni, Qing-Ling,Pan, Ying-Ming,Hong, Xue,Peng, Yan
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- A convenient one-pot synthesis of benzopyrimido[1,8]naphthyridines by knoevenagel condensation
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A series of 1-oxo-2,4-diphenyl-3-thioxobenzo[g]pyrimido[6,5-b]-1,8- naphthyridines has been synthesized by Knoevenagel condensation from 3-formyl-2-oxoquinolines and N,N-diphenyl-2-thiobarbituric acid on refluxing with liquid ammonia in absolute ethanol.
- Nandha Kumar,Suresh,Mohan
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- Design, synthesis and pharmacological evaluation of new 2-oxo-quinoline derivatives containing α-aminophosphonates as potential antitumor agents
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A series of novel 2-oxo-quinoline derivatives containing α-aminophosphonates were designed and synthesized as antitumor agents. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay results demonstrated that some compounds exhibited moderate to high inhibitory activity against HepG2, SK-OV-3 and NCI-H460 tumor cell lines, and most compounds showed much lower cytotoxicity against HL-7702 normal cells than 5-FU and cisplatin. The action mechanism of representative compound 5b was investigated by fluorescence staining assay, flow cytometric analysis and western blot (WB) assay, which indicated that this compound induced apoptosis and G2/M phase arrest accompanied by an increase in the production of intracellular Ca2+ and reactive oxygen species (ROS) and affecting associated enzymes and genes.
- Yu, Yan-Cheng,Kuang, Wen-Bin,Huang, Ri-Zhen,Fang, Yi-Lin,Zhang, Ye,Chen, Zhen-Feng,Ma, Xian-Li
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- Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties
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To develop novel antimicrobial agents, and based on the biologically active heterocyclic quinoline and thiazole substituted, a series of novel α-aminophosphonates (9a–h) and (10i–l) derivatives that incorporated quinoline or quinolone, and coumarylthiazole or 5-phenylthiazol-2-amine moieties were designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. All the new compounds were obtained in good yield with a simple workup and were confirmed using various spectroscopic methods. The in vitro antimicrobial activity of all synthesized compounds were screened in terms of MIC values against the selected strains of Gram-negative and Gram-positive bacteria and two fungal strains using the broth micro-dilution method. The results showed that most of the tested compounds showed moderate inhibitory activities against both Gram‐positive and ‐negative bacteria compared with reference drugs. The following compounds 9e, 9g, 9h, 9i and 9f, 9g, 9h, 10k, 10l are the most active against Gram-positive and Gram-negative bacteria strains, respectively, with MIC values ranging between 0.25 and 128 μg/mL. The synthesized compounds 9b, 9c, 9f, 9g, 9h, 10k, and 10l exhibited excellent antifungal inhibition with MIC values ranging between 0.25 and 32 μg/mL. Structure–activity relationship revealed that the presence of coumarylthiazole moiety and hydroxyl in the quinoline group increased the inhibitory activity against microbial strains pathogens. These results confirm that the synthesized compounds can be potential antimicrobial drugs candidate. [Figure not available: see fulltext.]
- Boukhari, Abbes,Djahoudi, Abdelghani,Litim, Bilal,Meliani, Saida
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- Lead Optimization of Influenza Virus RNA Polymerase Inhibitors Targeting PA-PB1 Interaction
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Influenza viruses are responsible for contagious respiratory illnesses in humans and cause seasonal epidemics and occasional pandemics worldwide. Previously, we identified a quinolinone derivative PA-49, which inhibited the influenza virus RNA-dependent RNA polymerase (RdRp) by targeting PA-PB1 interaction. This paper reports the structure optimization of PA-49, which resulted in the identification of 3-((dibenzylamino)methyl)quinolinone derivatives with more potent anti-influenza virus activity. During the optimization, the hit compound 89, which was more active than PA-49, was identified. Further optimization and scaffold hopping of 89 led to the most potent compounds 100 and a 1,8-naphthyridinone derivative 118, respectively. We conclusively determined that compounds 100 and 118 suppressed the replication of influenza virus and exhibited anti-influenza virus activity against both influenza virus types A and B in the range of 50% effective concentration (EC50) = 0.061-0.226 μM with low toxicity (50% cytotoxic concentration (CC50) >10 μM).
- Mizuta, Satoshi,Otaki, Hiroki,Ishikawa, Takeshi,Makau, Juliann Nzembi,Yamaguchi, Tomoko,Fujimoto, Takuya,Takakura, Nobuyuki,Sakauchi, Nobuki,Kitamura, Shuji,Nono, Hikaru,Nishi, Ryota,Tanaka, Yoshimasa,Takeda, Kohsuke,Nishida, Noriyuki,Watanabe, Ken
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p. 369 - 385
(2021/12/27)
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- Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety
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A series of new α-sulfamidophosphonate/sulfonamidophosphonate (4a–n) and cyclosulfamidophosphonate (5a–d) derivatives containing the quinoline or quinolone moiety was designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. This efficient methodology provides new 1,2,5-thiadiazolidine-1,1-dioxide derivatives 5a–d in one step and optimal conditions. The molecular structures of the novel compounds 4a–n and 5a–d were confirmed using various spectroscopic methods. All these compounds were evaluated for their in vitro antibacterial activity against Gram-negative (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) and Gram-positive (Staphylococcus aureus ATCC 27923) bacteria, in addition to three clinical strains (E. coli 1, P. aeruginosa 1, and S. aureus 1). Most of the tested compounds showed more potent inhibitory activities against both Gram-positive and -negative bacteria compared with the sulfamethoxazole reference. The following compounds, 4n, 4f, 4g, 4m, 4l, 4d, and 4e, are the most active sulfamidophosphonate derivatives. Furthermore, these molecules gave interesting zones of inhibition varying between 28 and 49 mm, against all tested bacterial strains, with a low minimum inhibitory concentration (MIC) value ranging from 0.125 to 8 μg/ml. All the synthesized derivatives were also evaluated for their in vitro antifungal activity against Fusarium oxyporum f. sp. lycopersici and Alternaria sp. The results revealed that all the synthesized compounds exhibited excellent antifungal inhibition and the compounds 4f, 4g, 4m, and 4i were the most potent derivatives with MIC values ranging from 0.25 to 1 μg/ml against the two tested fungal strains. The strongest inhibition of bacteria and fungi strains was detected by the effect of quinolone and sulfamide moieties.
- Bazine, Ismahene,Bendjedid, Samira,Boukhari, Abbes
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- Antimicrobial activity of quinoline-based hydroxyimidazolium hybrids
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Eight quinoline-based hydroxyimidazolium hybrids 7a-h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c-d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 μg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 μg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 μg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 μg/mL and full inhibition at 50 μg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 μg/mL (5 μM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 μg/mL (47 μM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 μg/mL (46 and 24 μM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.
- Abonia, Rodrigo,Bernal, Anthony,Guzman, Juan,Insuasty, Braulio,Insuasty, Daniel,Marquez, Edgar,Puerto, Gloria,Quiroga, Jairo,Svetaz, Laura,Vidal, Oscar,Zacchino, Susana
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- Catalyst-free assembly of giant tris(heteroaryl)methanes: Synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
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A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling reactions could also be carried out in water (at circa 80 °C) but with chemoselectivity favoring (Ar1Ar1Ar2)CH(Ar1Ar2Ar3)CH. The molecular structure of a representative (Ar1Ar2Ar3)CH triad was confirmed by X-ray analysis. Model tris(heteroaryl/aryl)methylium salts were generated by reaction with DDQ/HPF6 and studied by NMR and by DFT and GIAO-DFT.
- Abonia, Rodrigo,Gutiérrez, Luisa F.,Insuasty, Braulio,Quiroga, Jairo,Laali, Kenneth K.,Zhao, Chunqing,Borosky, Gabriela L.,Horwitz, Samantha M.,Bunge, Scott D.
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p. 642 - 654
(2019/04/17)
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- Synthesis, antiplasmodial and antitrypanosomal evaluation of a series of novel 2-oxoquinoline-based thiosemicarbazone derivatives
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Herein a series of novel thiosemicarbazones (TSCs) derived from 2-oxoquinoline scaffold is reported, and the target compounds have been successfully synthesized and characterized using standard spectroscopic techniques. The in vitro biological activities of synthesized molecules were evaluated against Plasmodium falciparum malaria parasites (strain 3D7), Trypanosoma brucei brucei parasites (strain 427) and HeLa cells. All the compounds displayed modest or no activity at a concentration of 20 μM and percentage viability of >50 % was often observed. Except for compound 9o, none of the final compounds exhibited cytotoxic effects against HeLa cells at 20 μM.
- Darrell, Oliver T.,Hulushe, Siyabonga T.,Mtshare, Thanduxolo E.,Beteck, Richard M.,Isaacs, Michelle,Laming, Dustin,Hoppe, Heinrich C.,Krause, Rui W.M.,Khanye, Setshaba D.
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p. 174 - 181
(2019/01/04)
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- Quinolinone derivative metal complex and its synthetic method and application
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The invention discloses a series of metal complexes of quinolinone derivatives, a synthesis method, and applications thereof. The synthesis method comprises the following steps: weighing metal salts and ligand 3-(1H-benzimidazole-2-yl)-6-methyl-2(1H)-quinolinone according to the stoichiometric ratio, dissolving the metal salts and ligand in a polar solvent, and carrying out coordination reactions to obtain the target products. The applicant also investigates the proliferation inhibition activity of the complexes on 4 human tumor cell strains and 1 normal cell strains. The results show that the complexes have a certain in-vitro antitumor activity; the activity of Rh(III) complexes is the most prominent, the antitumor activity of Rh(III) complexes on stomach cancer cell (MGC-803) is 5 times stronger than that of cis-platinum, furthermore, the toxicity of the complexes on the normal cells is smaller than the toxicity on cancer cells, the potential pharmaceutical value of the complexes is high, and the complexes are advantageously applied to the preparation of various antitumor drugs. The structure of the quinolinone metal complexes is shown in the description.
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- Quinolinone derivatives of the cobalt (II) complex and its synthetic method and application
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The invention discloses a cobalt (II) complex of quinolinone derivative, and a synthesis method and application thereof. The synthesis method of the quinolinone cobalt complex comprises the following steps: weighing cobaltous chloride and a ligand 3-(1H-benzimidazolyl-2-yl)-6-methyl-2(1H)-quinolinone according to the stoichiometric proportion, dissolving in a polar solvent, and carrying out complexing reaction. The research of the in-vitro antitumor activity indicates that the complex has certain proliferation inhibition activity for human cervical cancer cell Hela229, human stomach cancer cell MGC-803, human liver cancer cell strain Hep G2 and BEL-7404 cell strain, and has the maximum activity for human liver cancer cell strain Hep G2. The quinolinone cobalt complex is disclosed as the following formula (I).
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- 3-benzimidazole -2 (1H)-Quinolinone derivative and its preparation method and application (by machine translation)
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The present invention discloses a kind of 3-benzimidazole -2 (1H)-Quinolinone derivative and its preparation method and application. The preparation process of the derivative for the: heating 2 (1H)-Quinolinone derivatives and O-phenylene diamine derivatives soluble in organic solvent, the reaction is carried out under heating condition, to obtain. With commonly used anti-tumor drug 5-FU and compared with platinum, the derivative of the invention in the activity of certain derivatives of the more efficient, the normal human liver cell HL-7702 low toxicity. The invention the 3-benzimidazole -2 (1H)-Quinolinone derivative has if following type (I) the structure shown in: wherein R 1 is hydrogen, methyl, methoxy or R 2 form a 1,2-methylene-dioxy; R 2 is hydrogen or R 1 form a 1,2-methylene-dioxy; R 3 is hydrogen, methyl, methoxy, fluoro, chlorine-based, bromo, nitro or trifluoromethyl; R 4 is hydrogen, methyl, methoxy or chlorine-based. (by machine translation)
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Paragraph 0033; 0035; 0036
(2016/10/09)
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- Synthesis and anticancer activity of novel curcumin-quinolone hybrids
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A number of new curcumin-quinolone hybrids were synthesised from differently substituted 3-formyl-2-quinolones and vanillin and their in vitro cytotoxicity was determined on a panel of representative cell lines (A549, MCF7, SKOV3 and H460) using MTT assay. The most potent compound 14, was analysed for its mode of action using various cell biology experiments. SKOV3 cells treated with compound 14 showed distorted cell morphology under phase contrast imaging and induction of apoptosis was confirmed by Annexin V/PE assay. Further experiments on generation of reactive oxygen species (ROS) and cell cycle analysis revealed that these hybrids induce apoptosis by ROS generation and arrest cell cycle progression in S and G2/M phase.
- Raghavan, Saiharish,Manogaran, Prasath,Gadepalli Narasimha, Krishna Kumari,Kalpattu Kuppusami, Balasubramanian,Mariyappan, Palanivelu,Gopalakrishnan, Anjana,Venkatraman, Ganesh
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p. 3601 - 3605
(2015/08/11)
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- Novel quinoline-imidazolium adducts via the reaction of 2-oxoquinoline-3-carbaldehyde and quinoline-3-carbaldehydes with 1-butyl-3-methylimidazolium chloride [BMIM][Cl]
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A library of hydroxyquinolin-3-ylmethylimidazolium adducts were prepared in high yields from the reaction of [BMIM][Cl] with various substituted quinoline-3-carbaldehydes and 2-oxoquinoline-3-carbaldehydes under mild conditions by using sodium acetate in MeCN under ultrasound irradiation. The use of sodium acetate and imidazolium chloride was crucial for the success of these CC bond forming reactions. Attempted coupling with thiazolium bromide led instead to quinoline-3-carboxylic acid.
- Laali, Kenneth K.,Insuasty, Daniel,Abonia, Rodrigo,Insuasty, Braulio,Bunge, Scott D.
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p. 4395 - 4399
(2014/07/22)
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- Synthesis of some new pyrano[2,3-b]quinolines from 2-chloro-3-formylquinolones and Meldrum's acid
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A new series of functionalized pyrano[2,3-b]quinolines have been prepared in three steps from first condensation of 3-formyl-2-quinolones with Meldrum's acid, then the corresponding olefins have been alkylated using methyl magnesium iodide, and finally the target compounds have been obtained in good yields after hydrolysis.
- Guenfoud, Fatiha,Boulcina, Raouf,Laabassi, Mohammed,Mosset, Paul
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p. 736 - 742
(2015/04/14)
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- Synthesis and antitumor activities of some 2-oxo-quinoline-3-Schiff base derivatives
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A series of 2-oxo-quinoline-3-Schiff-base derivatives (4a1-4n2) have been designed and synthesized as new antitumor agents. in vitro Antitumor activities were evaluated against four cancer cell lines including MGC80-3, BEL-7404, A549 and NCI-H460. Compounds 4a1, 4a2, 4c2, 4d1, 4d2 and 4l2 exhibited better inhibition activities than commercial antitumor drug 5-fluorouracil (5-fluorouracil, IC50 = 44 ±0.54 μM) on NCI-H460, with IC50 of 35.52 ± 0.86, 16.22 ± 0.71, 11.62 ± 0.52, 5.16 ± 0.37, 7.62 ± 0.46 and 7.66 ± 0.65 μM, respectively.
- Fang, Yilin,Yi, Xianghui,Qin, Wen,Zhang, Ye,Liao, Yongzhi
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p. 7449 - 7451
(2015/04/22)
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- Synthesis and antioxidant activities of 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives
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A series of 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives 4a 1-4n2 were designed and synthesized based on the 2-oxo-quinoline structure core as novel antioxidants. In vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidants ascorbic acid, BHT and BHA, employing DPPH assay, ABTS+ assay, O2- assay and OH assay. The results showed that IC50 of most compounds were lower than standard value 10 mg/mL, indicating good antioxidant activities of these compounds. In addition, in vitro antioxidant activities screening revealed that 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities of compounds 4b2, 4e 1, 4e2 and 4g2, 2,2′-azinobis-(3- ethylbenzthiazoline-6-sulphonate) cation (ABTS+) radical scavenging activities of compounds 4a1, 4e1, 4e2, 4f 1, 4f2, 4g1, 4g2, 4h1, 4h2, 4k1, 4k2, 4n1 and 4n 2, superoxide anion radical scavenging activities of 4b1, 4e1, 4f2, 4j1, 4k1, 4k2, 4m1, 4m2, and 4n2, and hydroxyl radical scavenging activity of almost all the compounds except 4f1, 4f 2, 4j2, 4l1 and 4l2 were better than that of the commercial antioxidant butylated hydroxytoluene (BHT).
- Zhang, Ye,Fang, Yilin,Liang, Hong,Wang, Hengshan,Hu, Kun,Liu, Xianxian,Yi, Xianghui,Peng, Yan
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p. 107 - 111
(2013/02/23)
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- Zn(OTf)2-catalyzed three component, one-pot cyclocondensation reaction of some new octahydroquinazolinone derivatives and access their bio-potential
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An efficient synthesis of some new octahydroquinazolinone derivatives 4a-x by the cyclocondensation reaction of corresponding 2-thi(oxo)-1,2- dihydroquinoline-3-carbaldehyde 1a-e, 1,3-dicarbonyl compounds 2a-b, and substituted urea 3a-c using zinc triflat
- Shah, Pushpak M.,Patel, Manish P.
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p. 1188 - 1198
(2012/08/08)
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- Virtual screening based identification of novel small-molecule inhibitors targeted to the HIV-1 capsid
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The hydrophobic cavity of the C-terminal domain (CTD) of HIV-1 capsid has been recently validated as potential target for antiviral drugs by peptide-based inhibitors; however, there is no report yet of any small molecule compounds that target this hydrophobic cavity. In order to fill this gap and discover new classes of ant-HIV-1 inhibitors, we undertook a docking-based virtual screening and subsequent analog search, and medicinal chemistry approaches to identify small molecule inhibitors against this target. This article reports for the first time, to the best of our knowledge, identification of diverse classes of inhibitors that efficiently inhibited the formation of mature-like viral particles verified under electron microscope (EM) and showed potential as anti-HIV-1 agents in a viral infectivity assay against a wide range of laboratory-adapted as well as primary isolates in MT-2 cells and PBMC. In addition, the virions produced after the HIV-1 infected cells were treated with two of the most active compounds showed drastically reduced infectivity confirming the potential of these compounds as anti-HIV-1 agents. We have derived a comprehensive SAR from the antiviral data. The SAR analyses will be useful in further optimizing the leads to potential anti-HIV-1 agents.
- Curreli, Francesca,Zhang, Hongtao,Zhang, Xihui,Pyatkin, Ilya,Victor, Zagorodnikov,Altieri, Andrea,Debnath, Asim K.
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experimental part
p. 77 - 90
(2011/02/27)
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- QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS
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The present invention relates to novel quinolones of Formula I that inhibit inducible NOS synthase together with methods of synthesizing and using the compounds including methods for inhibiting or modulating nitric oxide synthesis and/or lowering nitric oxide levels in a patient by administering the compounds for the treatment of disease.
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- Synthesis of diastereomeric 2,4-disubstituted pyrano[2,3-b]quinolines from 3-formyl-2-quinolones through O-C bond formation via intramolecular electrophilic cyclization
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A number of 3-homoallyl-2-quinolones have been synthesized from 3-formyl-2-quinolones by reaction with allylindium bromide in aqueous DMF. Intramolecular electrophilic cyclization of these quinolones with iodine afforded either exclusively, or predominantly, racemic cis-diastereoisomers. Nucleophilic substitution reactions at the iodomethyl group afforded a mixture of tetracyclic products and unreacted racemic trans-diastereoisomer.
- Singh, Mrityunjay K.,Chandra, Atish,Singh, Bhawana,Singh, Radhey M.
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p. 5987 - 5990
(2008/02/10)
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- New syntheses of selenolo(2,3-b)quinoline-2-carboxylic ethyl esters
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The compounds selenolo(2, 3-b)quinoline-2-carboxylic ethyl esters were synthesized in varying yields by the reaction of (i) 3-(2-chloro-3-quinolyl) acrylic acids, (ii) 3-(2-chloro-3-quinolyl)acryloyl chlorides, and (iii) 2-chloro-3-(1,2-dibromo-3-quinolyl)acrylic ethyl esters with sodium diselenide in ethanol under a nitrogen atmosphere. Copyright Taylor & Francis Group, LLC.
- Nithyadevi,Rajendran
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p. 2623 - 2634
(2007/10/03)
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- Synthesis of selenolo(2,3-b)quinoline-2-carboxylic ethyl esters: Cytogenetic studies on human peripheral blood leucocyte cultures, and anti-bacterial studies, and anti-fungal studies of their effects
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The compounds selenolo(2,3-b)quinoline-2-carboxylic ethyl esters were synthesized in good yields by the reaction of 3-(2-chloro-3-quinolyl)acrylic ethyl esters, with the nucleophilic reagent sodium diselenide in ethanol medium under a nitrogen atmosphere. Cytogenetic studies on human blood leucocytes in vitro were evaluated for some of the synthesized compounds. Most of the synthesized compounds were tested for their antibacterial and antifungal activities. Copyright Taylor & Francis Inc.
- Nithyadevi,Rajendran
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p. 1849 - 1862
(2007/10/03)
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