An efficient synthesis of 4
            <i>H</i>
            -pyrano quinolinone derivatives catalysed by a versatile organocatalyst tetra-
            <i>n</i>
            -butylammonium fluoride and their pharmacological screening

Prasad, Pratibha; Shobhashana, Pratik G.; Patel, Manish P.

doi:10.1098/rsos.170764

Cited by 21 publications

(7 citation statements)

References 45 publications

(54 reference statements)

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“…Pyranoquinolone derivatives, both natural and synthetic, carry an extensive spectrum of medicinal and pharmacologic impacts, including anticoagulant properties [31], antitumor impact [32], microbial growth suppression [33], fungal treatment as well as anti-tubulin [34], anti-amoebiasis, anti-schistosomal [31][32][33][34][35][36][37][38], and anti-tuberculous measures [39][40][41][42]. Bio-organic chemistry relies on pyranoquinolone like molecules [43]. Additionally, pyranoquinoline structures are found in a number of alkaloids [6,44].…”

Section: Introductionmentioning

confidence: 99%

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Uppal

Mir

Chawla

et al. 2022

Journal of Heterocyclic Chem

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The search for new heterocyclic compounds with potential bioactivities continues despite the fact that extensive work has already been done on pyranoquinolones. Researchers throughout the world have used the pyranoquinolone nucleus extensively to generate a wide variety of bioactive heterocycles that target a wide spectrum of biological targets. An in-depth investigation into possible pyranoquinolone derivatives and their pharmacological importance is the focus of this overview of synthetic techniques. Researchers and medicinal chemists can benefit from this review by developing new pyranoquinolone nucleus leads that are very effective and have fewer adverse effects than existing ones.

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Section: Introductionmentioning

confidence: 99%

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Uppal

Mir

Chawla

et al. 2022

Journal of Heterocyclic Chem

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“…Different natural and synthetic pyranoquinoline have great clinical and pharmacological effects, such as antitumor [7,8] anticoagulant [9], antiproliferative activity [10], antimicrobial [11], antifungal and antitubulin [12], antiamebics and antischistosomal [5,13], anti-inflammatory, anti-Alzheimer and anti-tuberculosis activities [14][15][16]. As well as these compounds play an essential part in bioorganic chemistry [17]. On the other hand, these compounds are considered intermediates for the construction of azo dyestuffs [18,19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of some novel hetroaryl quinolinone derivatives

El‐Ghani

El-Sayed

El‐Desoky

2021

Journal of Heterocyclic Chem

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The aim of this study involves the synthesis of novel heterocyclic scaffolds containing quinoline moiety and studying their role as antimicrobial agents. 4‐hydroxy‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H))‐dione (1) was utilized as a precursor for the construction of new polyheterocyclic ring systems. It reacted with three aryl and (heteroaryl) aldehydes to furnish the corresponding arylidenes 2a‐c. The nucleophilic cyclization of compound 2 with hydrazine hydrate to give pyrazolyl quinolinone 3. Moreover, the reaction of 1 with HCHO/morpholine led to the formation of the adduct 7. The synthesized N‐(5–3‐formyl‐4‐hydroxy‐6‐phenyl‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano [3,2‐c] quinoline (10) was utilized for the synthesis of 3‐(([aryl]amino)methylene)‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,4,5 (3H,6H)‐trione 11a‐c via its treatment with three types of amines. Treatment of 1 with POCl3/Et3N afforded the corresponding 4‐chloro derivative 20. Which upon treatment with thiourea lead to the formation of the corresponding 4‐mercapto derivative 21. The latter 21 was alkylated using ethylbromo acetate giving 22. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses. The synthesized scaffolds were screened for antimicrobial activities also showed promising results. The p‐chlorobenzylidene pyrazolylquinolone derivative 3 has excellent antimicrobial properties against Proteus vulgaris compared to its mild activity against Staph aureus. While 4‐Chloro‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H)‐dione (20) exhibited good activates against Staph aureus surpassing the activity of reference antibiotic. Also, compounds 21 showed excellent antifungal activity against Candida albicans higher than fluconazole.

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“…[3,21] Indole-substituted compounds which are a nootropic drug developed for the treatment of Alzheimer's disease (AD) and they are used as potent non-steroidal anti-inflammatory agents which are more active than aspirin in the prophylactic and therapeutic adjuvant-induced polyarthritis models of chronic inflammation. [22] Several organic dyes, pigments and food colourants are derived from indole. [23] Spirooxoindoles have been synthesized and used in agriculture field as plant-produced hormones affecting plant growth including bud formation and root initiation beside to their significant antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

2020

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In the present work the authors could synthesize the substrates oxoketene gem-dithols 5, ketene dithioacetal 6 and 1,2dithiol-3-thione 39 from compounds bearing both nucleus indole and dihydropyrimidines together due to their biological and pharmacological activities. In this paper, and as a result of biological and pharmacological activities of oxoketene gemdithiols, ketene dithioacetal and/or 1,2-dithiol-3-thione; we synthesized various derivatives of them via indole and dihydropyrimidine in the form of either condensed or fused derivatives. We used ecofriendly methods such as pure orange juice as a green solvent and as an acid catalyst in the same time to prepare, 1-[2-imino-4-(1H-indol-3-yl)-6-methyl-1,2,3,4tetrahydropyrimidin-5-yl]-ethan-1-one 4a and/or 1-[4-(1H-Indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethan-1-one 4b. Subsequently, the substrate 4b was treated with different reagents to afford, 1-(4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-dimercaptoprop-2-en-1-one 5 and/or 1-(4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-bis(methylthio)prop-2-en-1-one 6. Compounds 5 and/or 6 were used as synthons to get various heterocyclic compounds such as 3-(4-(1H-indol-3-yl)-6-methyl-2-(piperidin-1-yl)-1,4-dihydropyrimidine-5-carbonyl)-2-thioxochroman-4-one 16 and/or 4'-(1H-indol-3-yl)-2-mercapto-6'-methyl-6-(methylthio)-2'-thioxo-1',2',3',4'-tetrahydro-[4,5'-bipyrimidine]-5-carbaldehyde 18. The newly synthesized compounds have been in vitro examined as antimicrobial agents, and some of them showed a promising activity. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H-NMR and MS.

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An efficient synthesis of 4 H -pyrano quinolinone derivatives catalysed by a versatile organocatalyst tetra- n -butylammonium fluoride and their pharmacological screening

Cited by 21 publications

References 45 publications

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Synthesis and biological evaluation of some novel hetroaryl quinolinone derivatives

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

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