80231-41-0Relevant articles and documents
Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes
Onysko,Lendel
, p. 1020 - 1023 (2007)
The reaction of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes with halogens gives 1-bromomethyl(bromomethylidene)-4-formyl-1,2-dihydrooxazolo[3,2- a]quinolinium halides.
Antimicrobial, Cytotoxicity and Molecular Docking Study of New Quinoline Schiff Base and its Metal(II) Complexes
Aghav, B. D.,Bellamkonda, R. O.,More, B. P.,Patil, S. K.,Vibhute, B. T.
, p. 685 - 694 (2022/02/22)
A new quinoline Schiff base ligand was synthesized by the reaction of 2-hydroxy-7-methylquinolin-3-carbaldehyde and 4-methylbenzene sulfonohydrazide. Synthesized Schiff base further utilized for the formation of stable metal complexes with Cu(II), Ni(II), Co(II) and Cd(II) metal salts and characterized by different spectroscopic techniques i.e. 1H NMR, 13C NMR, FT-IR, UV-visible, ESR, MASS and TGA. The low molar conductance values indicate that synthesized metal(II) complexes were non-electrolytes. The magnetic moment value indicates that Cu(II), Ni(II) and Co(II) complexes were paramagnetic. Further, these compounds were screened for inhibition activity against four bacterial strains, three fungal strains and cytotoxicity against the A-549 and MCF-7 cell lines by using the MTT method. Among the synthesized complexes, metal complexes exhibited excellent anticancer activity against the human lung cancer cell line (A-549). Schiff base and its Cd(II) complex showed good antibacterial activity. Furthermore, molecular docking study shows the significant binding affinity of metal complexes with tubulin protein. Present study proposed that all the synthesized Schiff base metal(II) complexes have excellent biological activity and could be act as potential anticancer agents.
Lead Optimization of Influenza Virus RNA Polymerase Inhibitors Targeting PA-PB1 Interaction
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
supporting information, p. 369 - 385 (2021/12/27)
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).
Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety
Bazine, Ismahene,Bendjedid, Samira,Boukhari, Abbes
, (2020/12/09)
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.
Synthesis, antioxidant and anticholinesterase activities of novel quinoline-aminophosphonate derivatives
Bazine, Ismahene,Bensegueni, Rafik,Bensouici, Chawki,Boukhari, Abbes,Cheraiet, Zinelaabidine
supporting information, (2020/03/04)
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).
An efficient one-pot synthesis, structure, antimicrobial and antioxidant investigations of some novel quinolyldibenzo[b,e][1,4]diazepinones
Parmar, Narsidas J.,Barad, Hitesh A.,Pansuriya, Bhavesh R.,Teraiya, Shashikant B.,Gupta, Vivek K.,Kant, Rajni
, p. 3816 - 3821 (2012/07/16)
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.
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
Singh, Mrityunjay K.,Chandra, Atish,Singh, Bhawana,Singh, Radhey M.
, p. 5987 - 5990 (2008/02/10)
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.
New syntheses of selenolo(2,3-b)quinoline-2-carboxylic ethyl esters
Nithyadevi,Rajendran
, p. 2623 - 2634 (2007/10/03)
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.
Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities
Srivastava, Ambika,Singh
, p. 1868 - 1875 (2007/10/03)
A simple and regioselective synthesis of 2-chloro-3-formylquinolines through Vilsmeier-Haack cyclisation of N-arylacetamides has been reported. The cyclisation is facilitated by N-arylacetamides bearing electron donating groups at m-position. However, yields of quinolines having electron donating groups are good in all cases. Further, the nucleophilic substitution reaction of the quinolines is also investigated. Similarly, the formyl group in the quinolines is subjected to further transformation into cyano (CAN-NH3) and alkoxycarbonyl (NIS-K2CO3/alcohols) groups to afford corresponding 3-cyano and 3-alkoxycarbonylquinolines, respectively.
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
Nithyadevi,Rajendran
, p. 1849 - 1862 (2007/10/03)
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.
