Synthesis, Reactions, and Biological Activities of Some New Thieno[3,2‐<i>c</i>]quinoline and Pyrrolo[3,2‐<i>c</i>]quinoline Derivatives

Abdel-Wadood, Fatma K.; Abdel-Monem, Maisa I.; Fahmy, A. M.; Geies, A. A.

doi:10.1002/ardp.201300167

Cited by 10 publications

(2 citation statements)

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“…[27] As halogen has a crucial role in the bioactivity of compounds and provides an avenue for further structure elaboration, halogencontaining quinolines are of particular interest. [28] Bromoquinolines are an important class of precursors for preparing heterocyclic compounds with multifunctionality. [7,29,30] These building blocks have especially been used within medicinal chemistry as starting materials for numerous compounds with a pharmacological activity.…”

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confidence: 99%

Quinoline‐based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors

Ökten

Aydın

Koçyiğit

et al. 2020

Archiv der Pharmazie

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A series of substituted quinolines was screened for their antiproliferative, cytotoxic, antibacterial activities, DNA/protein binding affinity, and anticholinergic properties by using the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide cell proliferation, lactate dehydrogenase cytotoxicity, and microdilution assays, the Wolfe–Shimmer equality method, the Ellman method, and the esterase assay, respectively. The results of the cytotoxic and anticancer activities of the compounds displayed that 6‐bromotetrahydroquinoline (2), 6,8‐dibromotetrahydroquinoline (3), 8‐bromo‐6‐cyanoquinoline (10), 5‐bromo‐6,8‐dimethoxyquinoline (12), the novel N‐nitrated 6,8‐dimethoxyquinoline (13), and 5,7‐dibromo‐8‐hydroxyquinoline (17) showed a significant antiproliferative potency against the A549, HeLa, HT29, Hep3B, and MCF7 cancer cell lines (IC50 = 2–50 μg/ml) and low cytotoxicity (∼7–35%) as the controls, 5‐fluorouracil and cisplatin. The compound–DNA linkages are hyperchromic or hypochromic, causing variations in their spectra. This situation shows that they can be bound to DNA with the groove‐binding mode, with Kb value in the range of 2.0 × 103–2.2 × 105 M–1. Studies on human Gram(+) and Gram(−) pathogenic bacteria showed that the substituted quinolines exhibited selective antimicrobial activities with MIC values of 62.50–250 μg/ml. All tested quinoline derivatives were found to be effective inhibitors of acetylcholinesterase (AChE) and the human carbonic anhydrase I and II isoforms (hCA I and II), with Ki values of 46.04–956.82 nM for hCA I, 54.95–976.93 nM for hCA II, and 5.51–155.22 nM for AChE. As a result, the preliminary data showed that substituted quinolines displayed effective pharmacological features. Molecular docking studies were performed to investigate the binding modes and interaction energies for compounds 2–17 with AChE (PDB ID: 4EY6), hCA I (PDB ID: 1BMZ), and hCA II (PDB ID: 2ABE).

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confidence: 99%

Quinoline‐based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors

Ökten

Aydın

Koçyiğit

et al. 2020

Archiv der Pharmazie

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“…Accordingly, combining both the thienopyrimidine and thienopyridine moieties in the same molecular framework ( i.e ., pyridothienopyrimidine 1 , Figure 2) has served as an attractive strategy for designing a novel scaffold with more favorable pharmacological properties [7]. In this study, as a part of our ongoing efforts to synthesize fused tricyclic heterocycles, dihydropyridinothienopyrimidin-4,9-dione derivatives 2 were prepared starting from benzylamine or p -methoxybenzylamine in six steps involving successive ring formations.…”

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confidence: 99%

Synthesis of Novel Dihydropyridothienopyrimidin-4,9-dione Derivatives

Kim

Park

et al. 2015

Molecules

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A novel molecular scaffold, dihydropyridothienopyrimidin-4,9-dione, was synthesized from benzylamine or p-methoxybenzylamine in six steps involving successive ring closure to form a fused ring system composed of dihydropyridone, thiophene and pyrimidone. The pharmacological versatility of the dihydropyridothenopyrimidin-4,9-dione scaffold was demonstrated by inhibitory activity against metabotropic glutamate receptor subtype 1 (mGluR1), which shows that the title compounds can serve as an interesting scaffold for the discovery of potential bioactive molecules for the treatment of human diseases.

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Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

Jin,

Shen,

2023

Chin. J. Chem.

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Comprehensive SummaryFused polycyclic N‐heterocycles are very important scaffolds in biomedicinal chemistry and materials science. Intramolecular alkyne hydroamination is a powerful method for the construction of N‐heterocycles. In the last two decades, copper‐catalyzed domino reactions based on intramolecular alkyne hydroamination has emerged as a robust strategy for assembling various fused polycyclic N‐heterocycles. Great progress has been achieved in this area. This short review covers the advances made in copper‐catalyzed domino synthesis of fused polycyclic N‐heterocycles based on the strategy from 2008 to 2023, and will hopefully serve as an inspiration towards the exploration of new copper‐catalyzed versions of the transformation. The domino transformations are introduced and discussed from five aspects according to the different key processes involved in these reactions.

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Synthesis, Reactions, and Biological Activities of Some New Thieno[3,2‐c]quinoline and Pyrrolo[3,2‐c]quinoline Derivatives

Cited by 10 publications

References 37 publications

Quinoline‐based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors

Quinoline‐based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors

Synthesis of Novel Dihydropyridothienopyrimidin-4,9-dione Derivatives

Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

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