Synthesis, antibacterial and anticancer evaluation of some new 2-chloro-3-hetarylquinolines

Bondock, Samir; Gieman, Hanaa

doi:10.1007/s11164-014-1899-8

Cited by 13 publications

(4 citation statements)

References 30 publications

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“…[13,14] The reactive N-substituted-2cyanoacetamide derivative 2 was allowed to react with both salicylaldehyde and 5-bromosalicylaldehyde in refluxing absolute ethanol containing piperidine as a base [12] to give the respective iminochromene compounds 3a and 3b, respectively. A plausible mechanism for the synthesis of chromene derivatives was illustrated to proceed via initial Knoevenagel condensation of the active methylene nitrile derivatives with carbonyl functions of salicylaldehyde and its derivatives to afford the arylidene intermediate followed by intramolecular 1,6dipolarcyclization via the addition of a phenolic OH function on the triple bond of the CN group to give iminochromene [15,16] . The piperidine was used in condensation processes as an effective base that catalysis the reaction in turn [17] (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

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As a continuation of our research on developing anticancer agents and based on the proven proprieties of thieno[2,3‐b]pyridines as anticancer, we have designed to synthesize novel thieno[2,3‐b]pyridine derivatives that incorporate different biologically active heterocycles through various chemical reactions. All of the newly obtained compounds, compared with the standard anticancer drug (doxorubicin), were screened in vitro for their antitumor activity against hepatocellular carcinoma (HepG‐2) and human breast cancer (MCF‐7) cell lines. The results revealed that compounds 3, 7, 12, and 19 were found to be the most potent against both HepG‐2 and MCF‐7 cell lines exhibiting IC50 values ranging from 3.67 to 11.50 and 5.13 to 11.80 μg/mL, respectively, among which compound 7 has a more potent activity than the reference drug doxorubicin against HepG‐2 cell line, showing IC50 value of 3.67 μg/mL (doxorubicin 4.65 μg/mL).

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Section: Resultsmentioning

confidence: 99%

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

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“…Previously, Selvi and Nadaraj [ 37 ] observed the transformation of 2-chloroquinoline-3-carbaldehyde into 2-oxo-1,2-dihydroquinoline-3-carbaldehyde in such a reaction environment (the milieu of acetic acid and sodium acetate) under the influence of microwave radiation. It seems that the presence of acetic acid was of decisive importance in this case since the reactions taking place with the participation of 2-chloroquinoline derivatives in ethanol medium and in the presence of piperidine did not lead to 2-oxo-1,2-dihydroquinoline derivatives [ 17 ]. The obtained compounds were characterized by very low solubility in popular solvents.…”

Section: Resultsmentioning

confidence: 99%

“…2-quinolone and benzo[d]thiazoyl hybrids reveal not only antitumor activity but also reduce the growth of Gram-negative bacteria [ 16 ]. 2-quinolone and 1,2,4-triazole hybrids and 2-quinolone and coumarin hybrids also show activity against Gram-negative bacteria [ 17 ]. An interesting antimalarial activity is demonstrated by 2-quinoline and pyrimidine-2-thione hybrids containing an aryl group at the nitrogen atom of the quinolone system [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light

et al. 2022

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Thiohydantoin and quinolone derivatives have attracted researchers’ attention because of a broad spectrum of their medical applications. The aim of our research was to synthesize and analyze the antimicrobial properties of novel 2-thiohydantoin and 2-quinolone derivatives. For this purpose, two series of hybrid compounds were synthesized. Both series consisted of 2-thiohydantoin core and 2-quinolone derivative ring, however one of them was enriched with an acetic acid group at N3 atom in 2-thiohydantoin core. Antibacterial properties of these compounds were examined against bacteria: Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae. The antimicrobial assay was carried out using a serial dilution method to obtain the MIC. The influence of blue light irradiation on the tested compounds was investigated. The relative yield of singlet oxygen (1O2*, 1Δg) generation upon excitation with 420 nm was determined by a comparative method, employing perinaphthenone (PN) as a standard. Antimicrobial properties were also investigated after blue light irradiation of the suspensions of the hybrids and bacteria placed in microtitrate plates. Preliminary results confirmed that some of the hybrid compounds showed bacteriostatic activity to the reference Gram-positive bacterial strains and a few of them were bacteriostatic towards Gram-negative bacteria, as well. Blue light activation enhanced bacteriostatic effect of the tested compounds.

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“…After completion of the reaction, the reaction mixture was quenched with NaHCO3 solution, extracted with DCM, and dried over Na2SO4. The organic layer was concentrated under reduced pressure to get a solid product [25,27,28] (Scheme 1).…”

Section: Synthesis Of 2-chloro-n'-((2-chloroquinolin-3-yl) Methylene)mentioning

confidence: 99%

Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives

2021

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The synthesis, antimicrobial, and antioxidant activities of new quinoline analogs were carried out with the aim to find possible hits/leads that can be taken up for future drug development. A series of 2-amino-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide derivatives (6a-h) have been synthesized by reacting 2-chloro-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide (5a) and N’-((6-bromo-2-chloroquinolin-3-yl)methylene)-2-chloroacetohydrazide (5b) with secondary amines (Morpholine, diethylamine, piperidine and 1-methylpiperazine). The characterization was achieved by FT-IR, 1H NMR, 13C NMR, and mass spectral analysis. The in silico ADMET studies of the synthesized molecules were analyzed for their drug likeliness and toxic properties. The ADMET study indicates that the synthesized compounds were found to be possessing reliable ADME properties and are nontoxic. The antimicrobial properties were tested against bacterial and fungal species with amoxicillin and fluconazole as standard drugs. The compounds 6a, 6c, 6e, and 6g exhibited good antibacterial potency against P. aeruginosa, and the compounds 6a, 6f, and 6h have shown good activity against E. coli with 1000 µg/mL. The compounds 6b, 6c, and 6e have moderate activity against fungal species C. oxysporum and the compounds 6c, 6e, 6f, 6g, and 6h have good activity against P. chrysogenum. Synthesized compounds were also tested for the DPPH· free radical scavenging activity to check the antioxidant potential, and the results revealed that the compounds 6a, 6b, 6c, and 6e have exhibited antioxidant potency than the remaining synthesized derivatives. The possible hits generated from biological activity could be taken for the generation of lead molecules for the drug discovery of antimicrobial and antioxidant entities from quinoline.

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Synthesis, antibacterial and anticancer evaluation of some new 2-chloro-3-hetarylquinolines

Cited by 13 publications

References 30 publications

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine

Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light

Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives

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