Design and synthesis of new pyranoquinolinone heteroannulated to triazolopyrimidine of potential apoptotic antiproliferative activity

Ramadan, Mohamed; Elaziz, Mohamed Abd; Elshaier, Yaseen A.M.M.; Youssif, Bahaa G.M.; Brown, Alan B.; Fathy, Hazem M.; Aly, Ashraf A.

doi:10.1016/j.bioorg.2020.104392

Cited by 21 publications

(13 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Absorption, delivery, metabolism, and excretion (ADME) testing became popular early in drug development programs, with computer models serving as feasible alternatives to experiments. The Swiss ADME website was used to predict the drug likeness profile of the studied compounds 1–21 [ 40 , 41 ]. Tables S1–S3 (Supplementary File) display the results of the drug likeness profile of these compounds.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

et al. 2021

View full text Add to dashboard Cite

A novel series of ciprofloxacin hybrids comprising various heterocycle derivatives has been synthesized and structurally elucidated using 1H NMR, 13C NMR, and elementary analyses. Using ciprofloxacin as a reference, compounds 1–21 were screened in vitro against Gram-positive bacterial strains such as Staphylococcus aureus and Bacillus subtilis and Gram-negative strains such as Escherichia coli and Pseudomonas aeruginosa. As a result, many of the compounds examined had antibacterial activity equivalent to ciprofloxacin against test bacteria. Compounds 2–6, oxadiazole derivatives, were found to have antibacterial activity that was 88 to 120% that of ciprofloxacin against Gram-positive and Gram-negative bacteria. The findings showed that none of the compounds tested had antifungal activity against Aspergillus flavus, but did have poor activity against Candida albicans, ranging from 23% to 33% of fluconazole, with compound 3 being the most active (33% of fluconazole). The most potent compounds, 3, 4, 5, and 6, displayed an IC50 of 86, 42, 92, and 180 nM against E. coli DNA gyrase, respectively (novobiocin, IC50 = 170 nM). Compounds 4, 5, and 6 showed IC50 values (1.47, 6.80, and 8.92 µM, respectively) against E. coli topo IV in comparison to novobiocin (IC50 = 11 µM).

show abstract

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Quinolone derivatives have been widely used in medicinal chemistry due to their unique structure, which exhibits a variety of pharmacological activities [3], especially antibacterial [4] and anti-cancer [5], with a promising role in the improvement of anti-cancer drug resistance [6]. Many quinolone derivatives exhibit excellent results in various operations, including growth inhibition via cell cycle arrest, apoptosis, and angiogenesis inhibition (Compounds I, II, and III, Figure 1) [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of (2-oxo-1,2-Dihydroquinolin-4-yl)-1,2,3-triazole Derivatives via Click Reaction: Potential Apoptotic Antiproliferative Agents

et al. 2021

Self Cite

View full text Add to dashboard Cite

A mild and versatile method based on Cu-catalyzed [2+3] cycloaddition (Huisgen-Meldal-Sharpless reaction) was developed to tether 3,3’-((4-(prop-2-yn-1-yloxy)phenyl)methylene)bis(4-hydroxyquinolin-2(1H)-ones) with 4-azido-2-quinolones in good yields. This methodology allowed attaching three quinolone molecules via a triazole linker with the proposed mechanism. The products are interesting precursors for their anti-proliferative activity. Compound 8g was the most active one, achieving IC50 = 1.2 ± 0.2 µM and 1.4 ± 0.2 µM against MCF-7 and Panc-1 cell lines, respectively. Moreover, cell cycle analysis of cells MCF-7 treated with 8g showed cell cycle arrest at the G2/M phase (supported by Caspase-3,8,9, Cytochrome C, BAX, and Bcl-2 studies). Additionally, significant pro-apoptotic activity is indicated by annexin V-FITC staining.

show abstract

Section: C 34fmentioning

confidence: 99%

“…12a-e Growth suppressive action against the majority of the tumor cell lines [16] 12. 12a Remarkable actions toward SR, K-562, MDA-MB-468 and MDA-MB and MCF7 [16] chemical, 12a's p53 assay findings indicated a 19-fold rise above those of non-treated cells [16]. Zhu et al have published the synthesis of pyranoquinolinones 17 by allowing mixtures of N-methyl-4-hydroxy quinolone, with Meldrum's acid and also aromatic aldehydes to react in the refluxing ethanol, with L-proline.…”

Section: C 34fmentioning

confidence: 99%

“…Based on the findings S C H E M E 1 7 Synthesis of heteroannulated pyranoquinolones presented above, it appears that compound 12a mostly causes a halt in the cell cycle during the Pre-G1 and G2/M phases. In addition, the molecule that was investigated is not carcinogenic but rather antiproliferative, meaning that it causes apoptosis and a cessation of cell cycle [16].…”

Section: C 34fmentioning

confidence: 99%

See 1 more Smart Citation

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Uppal

Mir

Chawla

et al. 2022

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

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.

show abstract

Design and synthesis of new pyranoquinolinone heteroannulated to triazolopyrimidine of potential apoptotic antiproliferative activity

Cited by 21 publications

References 56 publications

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

Design and Synthesis of (2-oxo-1,2-Dihydroquinolin-4-yl)-1,2,3-triazole Derivatives via Click Reaction: Potential Apoptotic Antiproliferative Agents

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Contact Info

Product

Resources

About