- Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations
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Novel O-alkylated quinoline and N-alkylated 4-quinolone derivatives attached to the ferrocene moiety through 4,1- (7a–d, 8a–d and 12a–d) and 1,4-disubstituted (9a, 9b, 10a and 10b) 1,2,3-triazole moiety were synthesized. The observed regioselectivity of O- vs. N-alkylation was explored by the use of NMR and computational techniques. Among the N-alkylated derivatives, the quinolone-ferrocene conjugate 9a displayed marked activities against chronic myeloid leukemia in blast crisis (K562) and Burkitt lymphoma (Raji). The 6-chloroquinolone-ferrocene conjugate 12c, with selective inhibitory activity on Raji cells and no cytostatic effect on normal MDCK1 cells was highlighted as the most promising anticancer organometallic complex in a group of O-alkylated quinolines.
- Mara?i?, Silvija,Lapi?, Jasmina,Djakovi?, Senka,Opa?ak-Bernardi, Teuta,Glava?-Obrovac, Ljubica,Vr?ek, Valerije,Rai?-Mali?, Silvana
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- Mapping Dual-Base-Enabled Nickel-Catalyzed Aryl Amidations: Application in the Synthesis of 4-Quinolones
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The C?N cross-coupling of (hetero)aryl (pseudo)halides with NH substrates employing nickel catalysts and organic amine bases represents an emergent strategy for the sustainable synthesis of (hetero)anilines. However, unlike protocols that rely on photoredox/electrochemical/reductant methods within NiI/III cycles, the reaction steps that comprise a putative Ni0/II C?N cross-coupling cycle for a thermally promoted catalyst system using organic amine base have not been elucidated. Here we disclose an efficient new nickel-catalyzed protocol for the C?N cross-coupling of amides and 2′-(pseudo)halide-substituted acetophenones, for the first time where the (pseudo)halide is chloride or sulfonate, which makes use of the commercial bisphosphine ligand PAd2-DalPhos (L4) in combination with an organic amine base/halide scavenger, leading to 4-quinolones. Room-temperature stoichiometric experiments involving isolated Ni0, I, and II species support a Ni0/II pathway, where the combined action of DBU/NaTFA allows for room-temperature amide cross-couplings.
- McGuire, Ryan T.,Lundrigan, Travis,MacMillan, Joshua W. M.,Robertson, Katherine N.,Yadav, Arun A.,Stradiotto, Mark
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- Design and synthesis of ibuprofen-quinoline conjugates as potential anti-inflammatory and analgesic drug candidates
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A new set of ibuprofen-quinoline conjugates comprising quinolinyl heterocycle and ibuprofen moieties linked by an alkyl chain were synthesized in good yields utilizing an optimized reaction procedure in a molecular hybridization approach to overcome the drawbacks of the current non-steroidal anti-inflammatory drugs. The synthesized conjugates were screened for their anti-inflammatory, and ulcerogenic properties. Several conjugates were found to have significant anti-inflammatory properties in the carrageenan-induced rat paw edema test without showing any ulcerogenic liability. In addition, most conjugates showed promising peripheral analgesic activity in the acetic acid-induced writhing test as well as central analgesic properties in the in vivo hot plate test. The most promising conjugates were the unsubstituted and 6-substituted fluoro- and chloro-derivatives of 2-(trifluoromethyl)quinoline linked to ibuprofen by a propyl chain. Their anti-inflammatory activity was evaluated against LPS-stimulated inflammatory reactions in RAW264.7 mouse macrophages. In this regard, it was found that most of the conjugates were able to significantly reduce the release and production of nitric oxide in the LPS-stimulated macrophages. The secretion and expression of the pro-inflammatory cytokines IL-6, TNF-α, and inducible nitric oxide synthase (iNOS) were also significantly suppressed.
- Ghanim, Amany M.,Girgis, Adel S.,Kariuki, Benson M.,Samir, Nermin,Said, Mona F.,Abdelnaser, Anwar,Nasr, Soad,Bekheit, Mohamed S.,Abdelhameed, Mohamed F.,Almalki, Ahmad J.,Ibrahim, Tarek S.,Panda, Siva S.
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- New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2
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At present therapeutic options for severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) are very limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-
- Seliem, Israa A.,Panda, Siva S.,Girgis, Adel S.,Moatasim, Yassmin,Kandeil, Ahmed,Mostafa, Ahmed,Ali, Mohamed A.,Nossier, Eman S.,Rasslan, Fatma,Srour, Aladdin M.,Sakhuja, Rajeev,Ibrahim, Tarek S.,Abdel-samii, Zakaria K.M.,Al-Mahmoudy, Amany M.M.
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- New trifluoromethyl quinolone derivatives: Synthesis and investigation of antimicrobial properties
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A series of quinolone derivatives, containing different heterocyclic amines were prepared. Synthesized compounds were evaluated for their in vitro antimicrobial activities against two Gram-positive bacteria, three Gram-negative bacteria as well as four fungi. All the derivatives showed good activity towards Gram-positive bacteria and less activity towards Gram-negative bacteria. They also showed moderate to comparable activity against Aspergillus niger and Candida albicans and low to moderate antifungal activity against Aspergillus fumigatus and Aspergillus flavus.
- Panda, Siva S.,Jain, Subhash C.
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p. 3225 - 3229
(2013/06/26)
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- Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones
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The acid-catalyzed cyclization-condensation between anilines and ethyl 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones (1), which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. These undergo halogen/metal exchange, generating 2-trifluoromethyl-4-quinolyllithiums, when treated with butyllithium, and hydrogen/metal exchange, generating 4-bromo-2-trifluoromethyl-3-quinolyllithiums, when treated with lithium diisopropylamide. Trapping of the latter intermediates provides 3-functionalized products that may be further elaborated by electrophilic substitution of the bromine atom. A few unexpected findings resulted from these investigations, the most noteworthy being an unprecedented buttressing effect and a counterintuitive halogen reactivity. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
- Marull, Marc,Schlosser, Manfred
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p. 1576 - 1588
(2007/10/03)
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- Synthesis of 1-(2-polyfluoroacylaminophenyl)-3-polyfluoroalkylpropane-1,3-diones and 2-polyfluoroalkyl-4-quinolones
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The condensation of 2-aminoacetophenone with RFCO2Et (RF = CF3, CF2H, CF2CF2H) in the presence of LiH in THF or ButOK in ButOH affords either 2-polyfluoroal
- Sosnovskikh,Usachev,Sizov
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p. 2109 - 2115
(2007/10/03)
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