6337-51-5Relevant academic research and scientific papers
In quest of small-molecules as potent non-competitive inhibitors against influenza
Malbari, Khushboo,Saha, Priyanka,Chawla-Sarkar, Mamta,Dutta, Shanta,Rai, Swita,Joshi, Mamata,Kanyalkar, Meena
, (2021/07/19)
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.
Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles
Lohrer, Bernhard,Bracher, Franz
, (2019/11/26)
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.
2-aryl-4-quinolone derivative as well as preparation method and application thereof
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Paragraph 0054-0060, (2018/10/19)
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.
Transition-metal-free oxidative intermolecular cyclization reaction: Synthesis of 2-aryl-4-quinolones
Ma, Haojie,Guo, Cui,Zhan, Zhenzhen,Lu, Guoqiang,Zhang, Yixin,Luo, Xinliang,Cui, Xinfeng,Huang, Guosheng
supporting information, p. 5280 - 5283 (2017/07/10)
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.
Mild, rapid and efficient metal-free synthesis of 2-aryl-4-aryloxyquinolines via direct Csp2[sbnd]O bond formation by using diaryliodonium salts
Nahide, Pradip D.,Solorio-Alvarado, César R.
, p. 279 - 284 (2017/01/03)
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
From Ketones, Amines, and Carbon Monoxide to 4-Quinolones: Palladium-Catalyzed Oxidative Carbonylation
Wu, Jiwei,Zhou, Yuchen,Wu, Ting,Zhou, Yi,Chiang, Chien-Wei,Lei, Aiwen
supporting information, p. 6432 - 6435 (2017/12/08)
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
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
Rode, Navnath D.,Arcadi, Antonio,Chiarini, Marco,Marinelli, Fabio
, p. 2501 - 2512 (2017/05/22)
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.
Silica-gel-supported Ce(SO4)2·4H2O-mediated cyclization of 2′-amino and 2′-hydroxychalcones under solvent-free conditions
Liu, Ruihuan,Zhang, Yan,Xu, Kangping,Tan, Guishan
supporting information, p. 1 - 9 (2016/12/30)
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.
Ruthenium(II) Catalyzed Regiospecific C-H/O-H Annulations of Directing Arenes via Weak Coordination
Banerjee, Arghya,Santra, Sourav Kumar,Mohanta, Prakash Ranjan,Patel, Bhisma K.
supporting information, p. 5678 - 5681 (2015/12/01)
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.
Aza analogs of flavones as potential antimicrobial agents
Sharma, Sahil,Thakur, Vikas,Ojha, Ritu,Budhiraja, Abhishek,Nepali, Kunal,Singh Bedi, Preet Mohinder
, p. 327 - 334 (2013/07/26)
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
