A comprehensive review on the biological interest of quinoline and its derivatives

Matada, Basavarajaiah Suliphuldevara; Pattanashettar, Raviraj S.; Yernale, Nagesh Gunavanthrao

doi:10.1016/j.bmc.2020.115973

Cited by 271 publications

(122 citation statements)

References 178 publications

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“…The arylation was found to be tolerant of various substituted substrates in moderate to good yields depending on the heteroarene. This late-stage C-2 arylation of these essential pharmacophores provided a practical strategy for the synthesis of attractive N -heterobiaryl derivatives that are widely found in pharmaceuticals and natural compounds, particularly in alkaloids [ 77 , 78 , 79 , 80 , 81 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Besson

Fruit

2021

Pharmaceuticals

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Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Besson

Fruit

2021

Pharmaceuticals

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“…In this context, the compounds with a quinoline nucleus belong to a diverse group of nitrogenated heterocycles prominent for their various pharmacological functions as antiplasmodial, antitumoral, leishmanicidal, among others [ 18 , 19 , 20 , 21 , 22 , 23 ]. Styrylquinolines (SQ) represent an alternative in the obtaining of chemical structures with potential applications in drug development against several infections, including those caused by parasites.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of the in vitro and in vivo antitrypanosomal activity of 2-styrylquinolines

Espinosa

Robledo

Guzmán

et al. 2021

Heliyon

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In this study, we report the synthesis and evaluation of in vitro and in vivo antitrypanosomal activity of styrylquinoline-like compounds (SQ) 3a-h . Synthesis was carried out by using quinaldine and 8- hydroxyquinaldine with a variety of aromatic aldehydes. The structure of SQs was corroborated by one and two-dimension NMR spectroscopy. In vitro antitrypanosomal activity on T. cruzi Talahuen strain was evaluated using β-galactosidase enzymatic method; cytotoxicity on U-937 cells was assessed by using MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] method. On the other hand, in vivo therapeutical response to 3a-f compounds was evaluated in BALB/c mice ( Mus musculus ) experimentally infected with T. cruzi blood trypomastigotes and then orally administered with 100 mg/kg weight day for 20 days. All of the compounds showed in vitro activity with EC 50 values ranging between 4.6 ± 0.1 μg/mL (14.4 μM) and 36.6 ± 6.1 μg/mL (91 μM). Furthermore, treatment with 3a-f compounds for 20 days resulted in improvement in all of the mice, with a 83–96% decrease in parasitic load at day 90 post-treatment. Treatment with benznidazol (BZ) managed to cure 100% of the mice at the end of treatment. None of the treatments affected the weight of the animals or alanine aminotransferase (ALT), blood urea nitrogen (BUN) and creatinine levels in serum. These results suggest a therapeutic potential of 3a-f compounds as treatment for the infection.

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“…In this work, as the continuation of our work on the development of anticancer agents, we designed and synthesized novel quinoline-chalcone derivatives as anticancer activity (Figure 3). Quinolines, as one class of N-containing heterocycles, have numerous advantages over other non-nitrogenous, which are widely used as "parental" compounds to synthesize molecules with variety of promising biological activity [16][17][18][19]. The quinoline motifs are frequently found in many compounds that show potent anticancer activity with different mechanisms [20][21][22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

“…Quinolines, as one class of N -containing heterocycles, have numerous advantages over other non-nitrogenous, which are widely used as “parental” compounds to synthesize molecules with variety of promising biological activity [ 16 , 17 , 18 , 19 ]. The quinoline motifs are frequently found in many compounds that show potent anticancer activity with different mechanisms [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity Studies of Novel Quinoline-Chalcone Derivatives

et al. 2021

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The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 µM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents.

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A comprehensive review on the biological interest of quinoline and its derivatives

Cited by 271 publications

References 178 publications

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Synthesis and evaluation of the in vitro and in vivo antitrypanosomal activity of 2-styrylquinolines

Design, Synthesis, and Anticancer Activity Studies of Novel Quinoline-Chalcone Derivatives

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