23789-85-7Relevant academic research and scientific papers
Synthesis of 4-quinolones via triflic anhydride-mediated intramolecular Houben-Hoesch reaction of β-arylamino acrylonitriles
Wu, Chenwei,Huang, Peng,Sun, Zhongqiao,Lin, Mi,Jiang, Yuchun,Tong, Jian,Ge, Chunhua
, p. 1461 - 1466 (2016)
A facile and efficient synthesis of 4-quinolones was described via intramolecular Houben-Hoesch reaction of β-arylamino acrylonitriles mediated by triflic anhydride in N,N-dimethylformamide.
4-Oxoquinolines and monoamine oxidase: When tautomerism matters
Mesiti, Francesco,Maruca, Annalisa,Silva, Vera,Rocca, Roberta,Fernandes, Carlos,Remi?o, Fernando,Uriarte, Eugenio,Alcaro, Stefano,Gaspar, Alexandra,Borges, Fernanda
, (2021/01/28)
4-Oxoquinoline derivatives have been often used in drug discovery programs due to their pharmacological properties. Inspired on chromone and 4-oxoquinoline chemical structure similarity, a small series of quinoline-based compounds was obtained and screened, for the first time, toward human monoamine oxidases isoforms. The data showed the N-(3,4-dichlorophenyl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide 10 was the most potent and selective MAO-B inhibitor (IC50 = 5.30 ± 0.74 nM and SI: ≥1887). The data analysis showed that prototropic tautomerism markedly influences the biological activity. The unequivocal characterisation of the quinoline tautomers was performed to understand the attained data. To our knowledge, there have been no prior reports on the characterisation of quinolone tautomers by 2D NMR techniques, namely by 1H–15N HSQC and 1H–15N HMBC, which are proposed as expedite tools for medicinal chemistry campaigns. Computational studies on enzyme-ligand complexes, obtained after MM-GBSA calculations and molecular dynamics simulations, supported the experimental data.
Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones
Sharma, Nidhi,Saha, Rajib,Parveen, Naziya,Sekar, Govindasamy
, p. 1947 - 1958 (2017/06/09)
A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).
Synthesis of 6-aryl substituted 4-quinolones via Suzuki cross coupling
Gupta, Sumanta,Ghosh, Prasanjit,Dwivedi, Seema,Das, Sajal
, p. 6254 - 6260 (2014/01/23)
A convenient way to introduce aryl functionalization in the 6-position of 4-quinolones is developed via selective bromination and subsequent arylation by Suzuki cross-coupling. Ethyl 4-quinolone 3-carboxylates were subjected to selective bromination at C-6 followed by arylation under microwave irradiation that yielded the desired cross-coupling products within 5 minutes. This approach can expediently be used for library synthesis of the aryl functionalized 4-quinolone derivative, an important class of biologically active compounds.
Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors
Chen, Shuguang,Chen, Ran,He, Meizi,Pang, Ruifang,Tan, Zhiwu,Yang, Ming
experimental part, p. 1948 - 1956 (2009/05/26)
Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat-TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory activities of blocking the Tat-TAR interaction. Molecular modeling experiments indicated that these compounds may inhibit Tat-TAR interaction by binding to Tat protein instead of TAR RNA.
Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2
Golub, Andriy G.,Yakovenko, Olexander Ya.,Bdzhola, Volodymyr G.,Sapelkin, Vladislav M.,Zien, Piotr,Yarmoluk, Sergiy M.
, p. 6443 - 6450 (2007/10/03)
Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitors-3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC 50 = 0.3 μM) and 4-oxo-1,4-dihydrobenzo[h]quinoline-3-carboxylic acid (9) (IC50 = 1 μM), are ATP competitive (Ki values are 0.06 and 0.28 μM, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.
