Synthesis, antitubercular, antimicrobial activities and molecular docking study of quinoline bearing dihydropyrimidines

Desai, N. C.; Kotadiya, G. M.; Jadeja, Krunalsinh A.; Shah, Keyur N.; Malani, Alimamad H.; Manga, Vijjulatha; Vani, Tamalapakula

doi:10.1016/j.bioorg.2021.105173

Cited by 15 publications

(5 citation statements)

References 48 publications

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“…It is important to note that the biological activity of dihydropyrimidines can vary depending on their chemical structure and specific substitutions on the molecule. Therefore, further research and development are needed to better understand their mechanisms of action and optimize their therapeutic potential [3,4].…”

Section: Introductionmentioning

confidence: 99%

Study of the biological properties of new chemical compounds of the pyrimidine series

Egorov,

Valiullin,

Raginov

et al. 2024

E3S Web Conf.

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In order to study the effect of a number of 6-substituted uracil derivatives on bovine embryo lung cells, experiments were conducted. According to the study, the effect of the studied substances on the cultural and morphological properties of cell was determined by taking into account their viability and proliferation index. In %, it was calculated that viability was determined by the ratio of living cells to their total number. The proliferation index was determined as the ratio of the number of proliferating cells to the number of seeded cells. At 0.1 mM concentration of the compounds studied, a decrease in LEK cell viability was recorded compared to the control group, but this was only the case for compound No. 2. When other compounds were used at doses of 0.1 mM, LEK cell viability increased by 3.0-7.0% compared to controls. Increasing the dose of the compounds studied to 1.0 mM results in a 10.0% decrease in survival in the presence of compounds No. 3 and 6, 16.0% in the presence of compounds No. 2 and 7, 19.0% in the presence of compound No. 4 and 25.0% in the presence of compounds No. 8 and 9.

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Section: Introductionmentioning

confidence: 99%

Study of the biological properties of new chemical compounds of the pyrimidine series

Egorov,

Valiullin,

Raginov

et al. 2024

E3S Web Conf.

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“…[4][5][6][7] Additionally, they hold promise in various therapeutic areas, including antimalarials, antituberculars, antibacterials, antihistamines, anti-neurodegeneratives, anticonvulsants, antitumor and anticancer agents, and antiallergics. [8][9][10] This diverse spectrum of potential applications underscores the ongoing interest and exploration of quinolines in the realm of medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…The true potential of quinolines lies in their remarkable range of biological activities, encompassing applications as analgesics, antiemetics, trypanocidal, antiseptics, and anti‐serotonin agents [4–7] . Additionally, they hold promise in various therapeutic areas, including antimalarials, antituberculars, antibacterials, antihistamines, anti‐neurodegeneratives, anticonvulsants, antitumor and anticancer agents, and antiallergics [8–10] . This diverse spectrum of potential applications underscores the ongoing interest and exploration of quinolines in the realm of medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Recent Advancements and Developments in the Biological Importance of Pyrimido[4,5‐b]Quinoline Scaffolds

Hammouda,

Rashed,

Abo El‐Yazeed

et al. 2024

ChemistrySelect

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This study highlights the biological efficiency of pyrimido[4,5‐b]quinolines as inhibitors of cancer cell growth and antioxidants and anti‐inflammatory properties, etc. Recent research studies have revealed their promising biological activity to inhibit the growth of many disease‐causing yeasts, fungi, and bacteria. The structural composition greatly affects the biological effectiveness, as these compounds exceed the value of some standard compounds against pathogenic microbes. The antioxidant potential of these derivatives is also explored. Several glycosylated and non‐glycosylated derivatives exhibited potent free radical scavenging activity and protected against DNA damage, exceeding reference standards in some cases. Furthermore, the review examines the anti‐inflammatory and analgesic properties of pyrimidoquinoline derivatives. Studies suggest their efficacy is comparable to known drugs like diclofenac and aspirin in carrageenan‐induced paw edema and hot plate tests. Pyrimidoquinoline derivatives also demonstrate promising anticancer activity. While some have minimal effects, others exhibit notable activity against various human cancer cell lines. This review documents over two decades of research, covering the period from 2000 to 2024. Overall, pyrimidoquinoline derivatives signify an auspicious class of compounds with therapeutic potential across various areas. Further research is necessary to elucidate their mechanisms of action, optimize their efficacy and selectivity, and assess their safety profiles for clinical development.

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“…Hence, this ring was provided several anticancer drugs to world such as belotecan, irinotecan and topotecan, (topoisomerase inhibitors), cabozantinib, foretinib, bosutinib, lenvatinib and neratinib (tyrosine kinase inhibitors). As well, quinoline based analogues were reported to show antimalarial, [5–6] antimicrobial, [7–8] antitubercular [9–10] and anticancer activtities [11–15] etc. As well, the pyrazole analogues were found to be proficient scaffolds in the medicinal chemistry and one of the mostly studied molecules amongst the azole's family.…”

Section: Introductionmentioning

confidence: 99%

“…As well, quinoline based analogues were reported to show antimalarial, [5][6] antimicrobial, [7][8] antitubercular [9][10] and anticancer activtities [11][12][13][14][15] etc. As well, the pyrazole analogues were found to be proficient scaffolds in the medicinal chemistry and one of the mostly studied molecules amongst the azole's family.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Quinoline‐Thiazolidine‐2,4‐dione Coupled Pyrazoles as in vitro EGFR Targeting Anti‐Breast Cancer Agents and Their in silico Studies

Bangaru¹,

Nukala²,

Kannekanti³

et al. 2023

ChemistrySelect

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The synthesis of some new quinoline‐thiazolidine‐2,4‐dione coupled pyrazoles (7 a–7 n) via Knoevengal condensation, N‐alkynylation and tandem one‐pot Sonogashira coupling‐cyclocondensation paths was described. All the compounds were further evaluated for their in vitro anti‐breast cancer activity against MDA‐MB‐231 and MCF‐7 and results were compared with standard drug erlotinib. Most of analogues were potent against MCF‐7 than the MDA‐MB‐231. In specific, compounds (Z)‐3‐((3‐(4‐methoxyphenyl)‐1H‐pyrazol‐5‐yl)methyl)‐5‐(quinolin‐4‐ylmethylene) thiazolidine‐2,4‐dione (7 d) and (Z)‐5‐(5‐((2,4‐dioxo‐5‐(quinolin‐4‐ylmethylene)thiazolidin‐3‐yl)methyl)‐1H‐pyrazol‐3‐yl)isophthalonitrile (7 m) had superior potency against MCF‐7 and MDA‐MB‐231 with IC50 (μg/mL) values ranging from 2.13 to 6.07. Besides, compounds (Z)‐3‐((3‐(3,5‐dimethoxyphenyl)‐1H‐pyrazol‐5‐yl)methyl)‐5‐(quinolin‐4ylmethylene)thiazolidine‐2,4‐dione (7 e), (Z)‐3‐((3‐(4‐chlorophenyl)‐1H‐pyrazol‐5‐yl)methyl)‐5‐(quinolin‐4‐ylmethylene)thiazolidine‐2,4‐dione (7 h), (Z)‐4‐(5‐((2,4‐dioxo‐5‐(quinolin‐4‐ylmethylene)thiazolidin‐3‐yl)methyl)‐1H‐pyrazol‐3‐yl)benzonitrile (7 i) and (Z)‐3‐((3‐(4‐nitrophenyl)‐1H‐pyrazol‐5‐yl)methyl)‐5‐(quinolin‐4‐ylmethylene)thiazolidine‐2,4‐dione (7 j) showed most promising potency against MCF‐7 with IC50 values 5.97‐6.43 μg/mL. The ability of compounds 7 d, 7 e, 7 h, 7 i, 7 j and 7 m to inhibit EGFR tyrosine kinase was also studied and found that compounds 7 d and 7 m showed remarkable potency as compared to erlotinib with inhibition 87.6 % and 91.4 % respectively. Molecular docking studies were then carried out for most potent compounds 7 d, 7 i, and 7 m and erlotinib on EGFR, and these compounds had encouraging binding energies and inhibition constants in comparison to erlotinib. Finally, compounds 7 d, 7 i and 7 m have high intestinal absorption with Caco‐2 permeability and followed Lipinski rules without any deviation.

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Synthesis, antitubercular, antimicrobial activities and molecular docking study of quinoline bearing dihydropyrimidines

Cited by 15 publications

References 48 publications

Study of the biological properties of new chemical compounds of the pyrimidine series

Study of the biological properties of new chemical compounds of the pyrimidine series

Recent Advancements and Developments in the Biological Importance of Pyrimido[4,5‐b]Quinoline Scaffolds

Synthesis of Quinoline‐Thiazolidine‐2,4‐dione Coupled Pyrazoles as in vitro EGFR Targeting Anti‐Breast Cancer Agents and Their in silico Studies

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