Reactions of 4‐Hydroxyquinolin‐2(1<i>H</i>)‐ones with Acenaphthoquinone: Synthesis of New 1,2‐Dihydroacenaphthylene‐spiro‐tetrakis(4‐hydroxyquinolin‐2(1<i>H</i>)‐ones)

Aly, Ashraf A.; Ramadan, Mohamed; Elreedy, Ahmed

doi:10.1002/jhet.3442

Cited by 9 publications

(5 citation statements)

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“…An example, 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinic acid derivatives I , were obtained by one-pot reaction of one equivalent of aromatic amines with two equivalents of diethyl malonate in diphenyl ether and catalyzed with triethylamine [14]. On reacting four equivalents of 4-hydroxyquinolin-2(1 H )-ones with one equivalent of acenaphthoquinone in absolute ethanol, containing catalytic Et 3 N, the reaction gave acenaphthylene-1,1,2,2-tetrayl-tetrakis- (4-hydroxyquinolin-2(1 H )-ones) ( II , [15]. We also reported that quinoline-2,4-diones reacted with 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile in pyridine to give spiro(indoline-3,4′-pyrano- [3,2- c ]quinoline)-3′-carbonitriles ( III , [16].…”

Section: Instructionmentioning

confidence: 99%

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Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

et al. 2019

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Section: Instructionmentioning

confidence: 99%

“…Structures of compounds that previously reported (Reproduced with permission from [14,15,16,17,18,19,20]).…”

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confidence: 99%

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Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

et al. 2019

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“…As an example, 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinic acid derivative I, was obtained by a one-pot reaction of one equivalent of aromatic amines with two equivalents of diethyl malonate in diphenyl ether and catalyzed with triethylamine [27] . A reaction of four equivalents of 4-hydroxyquinolin-2(1 H )-one with one equivalent of acenaphthoquinone gave acenaphthylene-1,1,2,2-tetrayl-tetrakis(4-hydroxyquinolin-2(1 H )-one) (II, [28] . We also reported that quinoline-2,4-dione reacted with 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile in pyridine to give spiro(indoline-3,4′-pyrano[3,2- c ]quinoline)-3′-carbonitrile (III, [29] , whereas 2-quinolone reacted with diethyl acetylenedicarboxylate to give pyrano[3,2- c ]quinoline-4-carboxylate (IV, [30] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of potentially new schiff bases of N-substituted-2-quinolonylacetohydrazides as anti-COVID-19 agents

Alshammari

Ramadan

Aly

et al. 2021

Journal of Molecular Structure

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Highlights Synthesis of new series of quinolone N -substituted-2-quinolonylacetohydrazides NMR spectral investigation of the newly prepared compounds. Molecular docking of the binding affinity to COVID-19 was done using Remdesivir as a reference Compound N' -(3-methoxybenzylidene)-2-quinolinacetohydrazide derivative showed high electron affinity towards COVID-19 and compared with Remdesivir

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“…[19] In light of our general aim to screen compounds of biological and pharmaceutical importance, we designed, synthesized, and screened a large variety of biologically active compounds. [20][21][22][23][24][25][26][27] The total number of people with diabetes has been projected to increase from 171 million in 2000 to 366 million by 2030. Diabetes mellitus (DM) is managed by insulin and oral administration of hypoglycemic drugs such as sulfonylureas and biguanides.…”

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Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents

Aly

Hassan

Makhlouf

et al. 2021

Archiv der Pharmazie

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New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data ( 1 H NMR, 13 C NMR, two-dimensional NMR, mass spectrometry, elemental analysis, and single-crystal X-ray analysis). The mechanism describing the formation of the products was also discussed.The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin-induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin-induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes. K E Y W O R D S4-substituted hydrazinecarbothioamides, antihyperglycemic activity, bis(2-(phenylsulfonyl)ethyl)sulfane, glutathione, malondialdehyde, sulfonylalkylthiosemicarbazide | INTRODUCTIONDue to the significant impact of sulfone compounds in biological applications, the development of new sulfone-containing compounds remains one of the central challenges of organic chemistry. [1,2] There are many sulfones widely reported in the literature with a broad spectrum of biological activities such as anticancer, [3] antimicrobial, [4] antiinflammatory, [5] antiproliferative, [6,7] antimalarial [8] and anti-HIV activities. [9] Catalytic chemoselective addition of amino alcohols to α,βunsaturated sulfonyl derivatives leads to the regioselective formation of amino and hydroxy adducts, depending on different catalysts and reaction conditions. [10,11] N-Substituted hydrazinecarbothioamides are considered as one of the most important classes of compounds containing nitrogen, sulfur, and oxygen used for heterocyclization and formation of different heterocyclic rings such as thiadiazole and thiadiazepine, and from the reaction with several π-deficient compounds. [12][13][14][15] The literature approach was applied to 4-(1-phenyl-1Htetrazole-5-ylsulfonyl)butanenitrile (PTSB), a growth inhibitory compound with a previously unknown mode of action, and the thioredoxin/ thioredoxin reductase system was identified as its target. [16] Another patent showed compounds having CH 2 CH 2 SO 2 Ar functional group as histone deacetylase inhibitors. [17][18] The synthesis of various heterocyclic

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Reactions of 4‐Hydroxyquinolin‐2(1H)‐ones with Acenaphthoquinone: Synthesis of New 1,2‐Dihydroacenaphthylene‐spiro‐tetrakis(4‐hydroxyquinolin‐2(1H)‐ones)

Cited by 9 publications

References 18 publications

Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

Synthesis of potentially new schiff bases of N-substituted-2-quinolonylacetohydrazides as anti-COVID-19 agents

Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents

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