Library design, synthesis and biological exploration of novel 3,4′-bicarbostyril derivatives as potent antimicrobial, antitubercular and antimalarial agents

Jardosh, Hardik H.; Vala, Nileshkumar D.; Patel, Manish P.

doi:10.1007/s00044-017-1797-x

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…Biologically active quinolone and benzoacridinones, pyridine derivatives synthesized from cyclohexane-1,3-dione derivatives. [70,78,87,88]…”

Section: Synthesis Of 14-dihydropyridine Derivativesmentioning

confidence: 99%

“…However, the starting material 1-allyl-2-oxo-1,2dihydroquinoline-3-carbaldehydes 39 was prepared by the electrophilic favoured N-allylation of 3-formylcarbotyril and βenaminone derivatives 40 were synthesized from nucleophilic addition reaction of cyclic-1,3-diones with different amines under solvent-free conditions (Scheme 32). [87] Scheme 29. Sulphonamide group bearing acridine-1,8-dione derivatives synthesis.…”

Section: Synthesis Of Acridine-18-dione Derivativesmentioning

confidence: 99%

“…Bicarbostyril derivatives synthesis from cyclohexane-1,3diones. [87] Scheme 33. Stepwise synthesis of different pyridine-2-one derivatives.…”

Section: Pyridine Derivatives Synthesismentioning

confidence: 99%

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Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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Cyclohexane‐1,3‐dione and its derivatives are imperative precursors in synthetic organic chemistry as they are useful intermediates for the synthesis of a wide range of biologically active natural products, heterocycles and pharmaceuticals. Recently, cyclohexane‐1,3‐diones have been used for the synthesis of varied array of six‐membered nitrogen‐containing heterocycles in the presence of aldehydes, acetoacetic esters, malononitrile, chalcones, coumarins, acetophenones, amino acids, amines, etc. under catalytic and non‐catalytic conditions. Newest studies on the importance of these heterocycles motivated us to compile all the recently developed processes which include the fabrication of six‐membered nitrogen heterocycles. This article is mainly focused on the efficient synthesis of six‐membered N‐heterocycles i. e. 1,4‐dihydropyridine, acridine‐1,8‐diones, benzoacridinones, quinolones and pyridine derivatives from cyclohexane‐1,3‐diones as one of the substrates, published for the last ten years.

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“…Biologically active quinolone and benzoacridinones, pyridine derivatives synthesized from cyclohexane-1,3-dione derivatives. [70,78,87,88]…”

Section: Synthesis Of 14-dihydropyridine Derivativesmentioning

confidence: 99%

Section: Synthesis Of Acridine-18-dione Derivativesmentioning

confidence: 99%

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Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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“…The main objectives of this paper are the synthesis of 3formyl-2(1H)-quinolones (3) and N-methyl-3-formyl-2-quinolones (4) substituted in the 6-position by either a methyl or a methoxy group, examination of their spectroscopic properties, and evaluation of their potential application as optical chemosensors for thiols. The presented derivatives of 2(1H)-quinolone (3 and 4) have been considered as substrates for the synthesis and application of novel dyes [38,39], as well as antimicrobial, anti-tumour, antibacterial and anti-fungal compounds [40][41][42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

The synthesis and spectroscopic characterisation of 3‐formyl‐2‐quinolones in the presence of biothiols

Grzelakowska

Kolińska

Mąkiewicz

2018

Coloration Technology

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The derivatives of 3-formyl-2(1H)-quinolones and N-methyl-3-formyl-2-quinolones substituted in the 6position with either a methyl or a methoxy group were synthesised and evaluated as potential sensors for the detection of thiol amino acids. Their spectroscopic properties, including absorption and emission spectra, fluorescence quantum yields and singlet lifetimes, were examined. The behaviour of the obtained compounds was studied at pH 7.4 in the presence of various amino acids. The results show that these compounds demonstrate a high turn-off fluorescence response and selectivity toward L-cysteine in the presence of other amino acids, and have the potential to act as sensors to L-cysteine.

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A Three‐Component Domino Reaction Enabled by Phase‐Transfer Catalysis for the Assembly of 3‐Thioquinoline‐2,5‐Diones

Chen,

Zhu

2024

Adv Synth Catal

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A three‐component phase‐transfer‐catalytic domino reaction involving cyclohexane‐1,3‐dione‐derived enaminones, 5‐alkenyl rhodanines, and haloalkanes has been developed. This protocol produces a wide range of 3‐thioquinoline‐2,5‐diones in yields of 52–81%. The construction of a C−S bond at the C‐3 position of the quinoline‐2,5‐dione framework expands its structural diversity. Studies into the reaction mechanism revealed that the reaction undergoes a conjugate addition, ammonolysis, elimination, and nucleophilic substitution sequence. The synthetic potential of the reaction was demonstrated by the gram‐scale syntheses of representative products. Chloroalkyl chains were installed on the sulfur atoms of most products obtained in this reaction. Diversified product derivatives were obtained by exploiting the favorable leaving nature of chloride moiety.

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Library design, synthesis and biological exploration of novel 3,4′-bicarbostyril derivatives as potent antimicrobial, antitubercular and antimalarial agents

Cited by 6 publications

References 28 publications

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

The synthesis and spectroscopic characterisation of 3‐formyl‐2‐quinolones in the presence of biothiols

A Three‐Component Domino Reaction Enabled by Phase‐Transfer Catalysis for the Assembly of 3‐Thioquinoline‐2,5‐Diones

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