Bisquinolones as chiral fluorophores – A combined experimental and computational study of absorption and emission characteristics

Uray, Georg; Kelterer, Anne‐Marie; Hashim, Jamshed; Glasnov, Toma N.; Kappe, C. Oliver; Fabian, Walter M. F.

doi:10.1016/j.molstruc.2009.04.009

Cited by 11 publications

(2 citation statements)

References 63 publications

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“…4‐Halo‐1,2‐dihydroquinolines prepared above should be versatile synthetic intermediates for the preparation of substituted heterocyclic compounds 8. Scheme exemplifies some applications 8q,r. From a representative product 9 , different types of side chains including an sp 3 , sp 2 , or sp carbon terminus were successfully introduced to its dihydroquinoline skeleton, illustrating the diverse synthesis from a common starting material.…”

Section: Methodsmentioning

confidence: 99%

Rhodium‐Catalyzed Intramolecular Hydroarylation of 1‐Halo‐1‐alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles

Murase

Senda

Senoo

et al. 2013

Chemistry A European J

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The regioselective intramolecular hydroarylation of (3-halo-2-propynyl)anilines, (3-halo-2-propynyl) aryl ethers, or (4-halo-3-butynyl) aryl ethers was efficiently catalyzed by Rh2(OCOCF3)4 to give semihydrogenated aromatic heterocycles, such as 4-halo-1,2-dihydroquinolines, 4-halo-3-chromenes, or 4-(halomethylene)chromans, in good to excellent yields. Some synthetic applications taking advantage of the halo-substituents of the products are also illustrated.

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Section: Methodsmentioning

confidence: 99%

Rhodium‐Catalyzed Intramolecular Hydroarylation of 1‐Halo‐1‐alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles

Murase

Senda

Senoo

et al. 2013

Chemistry A European J

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“…Bis-quinolones of type I ( Figure 1) occur naturally, and have fluorescent properties and biological activity [24,25]. In a recent communication [26], the synthesis of the zwitter-ionic 4-hydroxycoumarin derivatives II ( Figure 1) was reported, through a unique reaction of 4-hydroxycoumarins with p-benzoquinone and pyridine in aqueous acetone.…”

mentioning

confidence: 99%

Synthesis of novel 1,2-bis-quinolinyl-1,4-naphthoquinones: ERK2 inhibition, cytotoxicity and molecular docking studies

Aly

El‐Sheref

Bakheet

et al. 2018

Bioorganic Chemistry

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Two novel series of N-2,3-bis(6-substituted-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-diones 3a-d and substituted N-(methyl/ethyl)bisquinolinone triethyl-ammonium salts 4e,f were successfully synthesized. The synthesized compounds were targeted as new candidates to extracellular signal-regulated kinases 1/2 (ERK1/2) with considerable antineoplastic activity. The synthesis involved the reactions of 2 equivalents of 4-hydroxy-2(1H)-quinolinones 1a-f and one equivalent of 1,4-naphthoquinone (2) in a mixture of ethanol/dimethylformamide (1:1) as a solvent and 0.5 mL EtN. In the reaction of 6-methyl-4-hydroxyquinolone 1b with 2, a side product 4b of the second series was obtained. In general, the presence of free NH-quinolone gave a single compound of the first series, whereas reaction of N-methyl/ethyl-quinolones 1e,f with 2 enhanced the formation of compounds of the second series. The structures of the new compounds were proved by different spectroscopic techniques such as IR, NMR (2D-NMR) and mass spectra, elemental analysis, and X-ray crystallography. To further elucidate the mechanism of action of these newly synthesized compounds, compounds 3a, 3b, 4e and 4f were selected to investigate for their MAP Kinases pathway inhibition together with molecular docking using ATP-binding site of ERK2. The results revealed that compounds 3a, 3b and 4f inhibited ETS-1 phosphorylation by ERK2 in a dose dependent manner. Also, compound 4f showed highest potency for ERK2 inhibition with ATP-competitive inhibition mechanism which was confirmed by the formation of three hydrogen bond in the molecular docking studies. The synthesized compounds were then tested for their in vitro anticancer activity against the NCI-60 panel of tumor cell lines. Interestingly, the selected compounds displayed from modest to strong cytotoxic activities. Compound 3b demonstrated broad spectrum anti-tumor activity against the nine tumor sub-panels tested, while compound 3d proved to be lethal to most of the cancer cell lines as shown by their promising GI and TGI values in NCI in vitro five dose testing. These results revealed that the synthesized compounds can potentially serve as leads for the development of novel chemotherapeutic agents and structure improvement will be necessary for some derivatives for enhancing their cellular activities and pharmacokinetic profile.

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Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

Wang

Cui

Li³

et al. 2011

Eur J Org Chem

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The tricyclohexylphosphane adduct of cyclopalladated ferrocenylimine I exhibited high catalytic activity in the one‐pot borylation/Suzuki–Miyaura coupling (BSC) reaction with low catalyst loading (2 mol‐%). Various biaryls were obtained in good to excellent yields for 37 examples. This process was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups and did not require an excess amount of phosphane ligand and the addition of the palladium catalyst in the second step.

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Bisquinolones as chiral fluorophores – A combined experimental and computational study of absorption and emission characteristics

Cited by 11 publications

References 63 publications

Rhodium‐Catalyzed Intramolecular Hydroarylation of 1‐Halo‐1‐alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles

Rhodium‐Catalyzed Intramolecular Hydroarylation of 1‐Halo‐1‐alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles

Synthesis of novel 1,2-bis-quinolinyl-1,4-naphthoquinones: ERK2 inhibition, cytotoxicity and molecular docking studies

Synthesis of Biaryls through a One‐Pot Tandem Borylation/Suzuki–Miyaura Cross‐Coupling Reaction Catalyzed by a Palladacycle

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