- In quest of small-molecules as potent non-competitive inhibitors against influenza
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A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.
- Malbari, Khushboo,Saha, Priyanka,Chawla-Sarkar, Mamta,Dutta, Shanta,Rai, Swita,Joshi, Mamata,Kanyalkar, Meena
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- Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles
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Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.
- Lohrer, Bernhard,Bracher, Franz
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- 2-aryl-4-quinolone derivative as well as preparation method and application thereof
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The invention discloses a 2-aryl-4-quinolone derivative as well as a preparation method and an application thereof. The 2-aryl-4-quinolone derivative has the structure shown in formula (I) in the description, wherein R1 is independently selected from one or more of H, C1-C5 alkyl, halogen or C1-C5 alkoxy, and R2 is independently selected from one or more of H, C1-C5 alkyl, CF3, halogen or C1-C5 alkoxy. Test results show that the 2-aryl-4-quinolone derivative has good antibacterial activity and can be used as an antibacterial agent.
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Paragraph 0054-0060
(2018/10/19)
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- Transition-metal-free oxidative intermolecular cyclization reaction: Synthesis of 2-aryl-4-quinolones
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Herein, a novel and efficient intermolecular cyclization of 2-aminoacetophenones with aldehydes was developed for the synthesis of 2-aryl-4-quinolones through C-C and C-N bond formation. Mild conditions, good functional group tolerance, and substrates without prefunctionalization make this protocol practical, and this strategy will stimulate keen interest in fields of chemistry and biology.
- Ma, Haojie,Guo, Cui,Zhan, Zhenzhen,Lu, Guoqiang,Zhang, Yixin,Luo, Xinliang,Cui, Xinfeng,Huang, Guosheng
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supporting information
p. 5280 - 5283
(2017/07/10)
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- From Ketones, Amines, and Carbon Monoxide to 4-Quinolones: Palladium-Catalyzed Oxidative Carbonylation
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A novel method of palladium-catalyzed oxidative carbonylation of ketones, amines, and carbon monoxide for the synthesis of 4-quinolones has been developed. This protocol provides a straightforward route to construct useful 4-quinolone derivatives from ine
- Wu, Jiwei,Zhou, Yuchen,Wu, Ting,Zhou, Yi,Chiang, Chien-Wei,Lei, Aiwen
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supporting information
p. 6432 - 6435
(2017/12/08)
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- An Improved Environmentally Friendly Approach to 4-Nitro-, 4-Sulfonyl-, and 4-Aminoquinolines and 4-Quinolones through Conjugate Addition of Nucleophiles to β-(2-Aminophenyl)-α,β-ynones
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Sequential addition/annulation reactions of sulfinate and nitrite anions to β-(2-aminophenyl)-α,β-ynones led to valuable 4-sulfonylquinolines and 4-nitroquinolines. The latter proved to be versatile precursors of N-unsubstituted 4-aminoquinolines and 4-quinolones. Reaction of β-(2-aminophenyl)-α,β-ynones with DMF/NaOH resulted in the formation of 4-(dimethylamino)quinolines. The use of an alternative CO-free procedure for the preparation of substrates β-(2-aminophenyl)-α,β-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.
- Rode, Navnath D.,Arcadi, Antonio,Chiarini, Marco,Marinelli, Fabio
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p. 2501 - 2512
(2017/05/22)
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- Silica-gel-supported Ce(SO4)2·4H2O-mediated cyclization of 2′-amino and 2′-hydroxychalcones under solvent-free conditions
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A simple, efficient, and environmentally friendly approach for the synthesis of flavones, aza-flavones, and aza-flavanones from corresponding 2′-hydroxy or 2′-aminochalcones has been developed. The reactions are successfully conducted in presence of silica-gel-supported Ce(SO4)2·4H2O under solvent-free conditions.
- Liu, Ruihuan,Zhang, Yan,Xu, Kangping,Tan, Guishan
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supporting information
p. 1 - 9
(2016/12/30)
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- Mild, rapid and efficient metal-free synthesis of 2-aryl-4-aryloxyquinolines via direct Csp2[sbnd]O bond formation by using diaryliodonium salts
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An efficient ligand- and transition metal-free procedure for the direct Csp2[sbnd]O bond formation for the arylation of 2-aryl-4-quinolones was developed. The synthesis of the starting quinolones was carried out under our optimized C
- Nahide, Pradip D.,Solorio-Alvarado, César R.
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p. 279 - 284
(2017/01/03)
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- Ruthenium(II) Catalyzed Regiospecific C-H/O-H Annulations of Directing Arenes via Weak Coordination
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Ruthenium(II) catalyzed oxidative C-H/O-H annulations have been demonstrated using two different directing arenes viz. 2-arylquinolinone and 2-arylbenzoxazinone with internal alkynes. Regiospecific annulations have been observed for both directing arenes via the assistance of weaker carbonyl oxygen in the presence of a stronger nitrogen-directing site. In this substrate-controlled convergent protocol the weaker directing group dictates the annulation path.
- Banerjee, Arghya,Santra, Sourav Kumar,Mohanta, Prakash Ranjan,Patel, Bhisma K.
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supporting information
p. 5678 - 5681
(2015/12/01)
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- Design and synthesis of aza-flavones as a new class of xanthine oxidase inhibitors
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In an attempt to develop non-purine-based xanthine oxidase (XO) inhibitors, keeping in view the complications reported with the use of purine-based XO inhibitors, the flavone framework (a class possessing XO inhibitory potential) was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone (a bicyclic unit present in flavones), owing to the bioactive potential and drug-like properties of quinolones. This type of replacement does not alter the shape and structural features required for XO inhibition, and also provides some additional interaction sites, without the loss of hydrogen bonding and hydrophobic and arene-arene interactions. In the present study, a series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was rationally designed, synthesized and evaluated for in vitro XO inhibitory activity. Some notions about structure-activity relationships are presented indicating the influence of the nature of the 2-aryl ring on the inhibitory activity. Important interactions of the most active compound 3l (IC50 = 6.24 μM) with the amino acid residues of the active site of XO were figured out by molecular modeling. To develop non-purine-based xanthine oxidase inhibitors, the flavone framework was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone. This type of replacement does not alter the shape and structural features required for xanthine oxidase inhibition. The rationally designed and synthesized series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was evaluated for in vitro xanthine oxidase inhibitory activity. Copyright
- Dhiman, Rajni,Sharma, Sahil,Singh, Gagandip,Nepali, Kunal,Singh Bedi, Preet Mohinder
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- Aza analogs of flavones as potential antimicrobial agents
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In search for the new antimicrobial agents owing to drug resistant bacteria and fungi, a series of rationally designed aza analogs of flavones has been designed and synthesized. The design of the analogs involved incorporation of quinolone nucleus within
- Sharma, Sahil,Thakur, Vikas,Ojha, Ritu,Budhiraja, Abhishek,Nepali, Kunal,Singh Bedi, Preet Mohinder
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p. 327 - 334
(2013/07/26)
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- An efficient one-step synthesis of 2-arylquinolin-4(1H)-ones with the aid of a low-valent titanium reagent
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A short and facile synthesis of a series of 2-arylquinolin-4(1H)-ones was accomplished in good yields via the novel reductive cyclization of 2-nitrochalcones promoted by TiCl4/Zn. This method has the advantages of accessible starting materials,
- Sun, Fang,Zhao, Xuan,Shi, Daqing
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supporting information; experimental part
p. 5633 - 5635
(2011/11/06)
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- Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2′-aminoacetophenones
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The syntheses of a diverse set of 2-aryl-4-quinolone derivatives were achieved by exposing corresponding acylated 2′-aminoacetophenones to microwave irradiation in the presence of NaOH. The microwave accelerated cyclizations were complete within 10-22 min
- Ding, Derong,Li, Xin,Wang, Xin,Du, Yongli,Shen, Jingkang
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p. 6997 - 6999
(2007/10/03)
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- Tautomeric 2-arylquinolin-4(1H)-one derivatives- spectroscopic, X-ray and quantum chemical structural studies
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A convenient method for the synthesis of 2-aryl-1-methylquinolin-4(1H) -ones is described. Spectroscopic and X-ray crystallographic techniques as well as quantum chemical calculations have been used to probe the structure of potentially tautomeric 2-arylq
- Mphahlele, Malose J.,El-Nahas, Ahmed M.
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p. 129 - 136
(2007/10/03)
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- Hypervalent iodine oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones : An easy access to 2-aryl-4-quinolones
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Oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones (1a-e) using iodobenzene diacetate in methanolic potassium hydroxide leads to dehydrogenation of 1 thereby providing an easy access to 2-aryl-4-quinolones (2a-e).
- Prakash,Kumar,Saini,Singh
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p. 2167 - 2172
(2007/10/02)
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- Intramolecular Amination of Olefins. Synthesis of 2-Substituted-4-quinolones from 2-Nitrochalcones catalysed by Ruthenium
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2-Substituted-4-quinolones 2 and the correspnding 2,3-dihydro-2-substituted-4-quinolones 3 have been obtained by reduction with CO at 170 deg C and 30 atm of 2-nitrochalcones 1, catalysed by Ru3(CO)12 with DIAN-Me as co-catalyst in ethanol-water.
- Tollari, Stefano,Cenini, Sergio,Ragaini, Fabio,Cassar, Lucia
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p. 1741 - 1742
(2007/10/02)
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- A new route to 2-aryl-4-quinolones via thallium(III) p-tolylsulphonate mediated oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones
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Oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones (1a-f) to 2-aryl-4-quinolones (2a-f) using thallium(III) p-tolylsulphonate in refluxing dimethoxyethane has been described. A mechanistic scheme for this new transformation has been proposed.
- Singh,Kapil
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p. 277 - 283
(2007/10/02)
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- 4-Piperidino-2-phenylquinolines
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Disclosed are compounds of the formula STR1 wherein: R1 and R2 may be either the same or different and each is hydrogen or lower alkyl; and wherein R3 and R4 may be either the same or different and each is hydrogen, halogen, or lower alkyl, with the proviso that R3 and R4 cannot both be hydrogen. These compounds are useful as anticonvulsant or anxiolytic agents.
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