Synthesis of new 2- and 3-hydroxyquinoline-4-carboxylic acid derivatives as potential antioxidants

Massoud, Mohammed A. M.; Bialy, Serry A. El; Bayoumi, Waleed A.; Husseiny, Walaa M. El

doi:10.1515/hc-2013-0163

Cited by 11 publications

(5 citation statements)

References 27 publications

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“…The mass ion peaks at m/z 259.1089478, 190.049843, 227.1178055, and 238.0722198 for the predicted molecular formulas C 14 H 16 N 2 O 3 , C 10 H 7 NO 3 , C 14 H 14 N 2 O, and C 11 H 13 NO 5 were dereplicated as diketopiperazine derivative maculosin (33), antioxidant 3-Hydroxyquinoline-2-carboxylic acid (34), benzodiazepine derivative antitumor antibiotic prothracarcin (35), and amino acid N-acetyl-3,4-dihydroxy-L-phenylalanine (36), respectively which were previously detected in Streptomyces rochei 87051-3 [105], Streptomyces cyaneofuscatus M-157 [106,107], Streptomyces umbrosus [108,109], and Streptomyces akiyoshiensis ATCC13480 L127 mutants [110], respectively. Whereas that at m/z 303.1353149, corresponding to the suggested molecular formula C 16 H 20 N 2 O 4 was dereplicated as benzodiazepine derivative antitumor antibiotic tomaymycin (37), which was formerly reported from Streptomyces achromogenes-tomaymyceticus [111,112].…”

Section: Chemical Dereplication Of Strain Ua17 With Mycolic Acidmentioning

confidence: 93%

Actinomycetes from the Red Sea Sponge Coscinoderma mathewsi: Isolation, Diversity, and Potential for Bioactive Compounds Discovery

et al. 2020

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The diversity of actinomycetes associated with the marine sponge Coscinoderma mathewsi collected from Hurghada (Egypt) was studied. Twenty-three actinomycetes were separated and identified based on the 16S rDNA gene sequence analysis. Out of them, three isolates were classified as novel species of the genera Micromonospora, Nocardia, and Gordonia. Genome sequencing of actinomycete strains has revealed many silent biosynthetic gene clusters and has shown their exceptional capacity for the production of secondary metabolites, not observed under classical cultivation conditions. Therefore, the effect of mycolic-acid-containing bacteria or mycolic acid on the biosynthesis of cryptic natural products was investigated. Sponge-derived actinomycete Micromonospora sp. UA17 was co-cultured using liquid fermentation with two mycolic acid-containing actinomycetes (Gordonia sp. UA19 and Nocardia sp. UA 23), or supplemented with pure mycolic acid. LC-HRESIMS data were analyzed to compare natural production across all crude extracts. Micromonospora sp. UA17 was rich with isotetracenone, indolocarbazole, and anthracycline analogs. Some co-culture extracts showed metabolites such as a chlorocardicin, neocopiamycin A, and chicamycin B that were not found in the respective monocultures, suggesting a mycolic acid effect on the induction of cryptic natural product biosynthetic pathways. The antibacterial, antifungal, and antiparasitic activities for the different cultures extracts were also tested.

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Section: Chemical Dereplication Of Strain Ua17 With Mycolic Acidmentioning

confidence: 93%

Actinomycetes from the Red Sea Sponge Coscinoderma mathewsi: Isolation, Diversity, and Potential for Bioactive Compounds Discovery

et al. 2020

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“…The quinoline-benzimidazole derivative was synthesized from the previous quinoline derivative based on the adaptation of the reported method. [ 13 ] The synthesized quinoline derivative (1 mmol) and o-phenylenediamine (1 mmol) were mixed and pounded using a mortar and pestle at room temperature, then heated for 1 h at 140°C. The molten mixture was then added to ice-cold water once it had cooled to room temperature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of antioxidant and antimicrobial bioactive compounds based on the quinoline-hydrazone and benzimidazole structure

Cahyana

Halim²,

Amaliyah³

2023

Journal of Advanced Pharmaceutical Technology &Amp; Research

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Quinoline and its derivatives are known to have various biological activities such as antibacterial and antioxidant. Therefore, this study aims to synthesize quinoline moiety from isatin and ethyl acetoacetate by Pfitzinger reaction under acidic conditions. The benzimidazole derivative was synthesized from quinoline and o-phenylenediamine by a solvent-less reaction, while the hydrazone derivative was formed by the reaction with hydrazine hydrate and aromatic aldehyde. In addition, 4-hydroxybenzaldehyde was used as an aromatic aldehyde. The four compounds formed were characterized by thin-layer chromatography (TLC), melting point measurement, Fourier-transform infrared, liquid chromatography–mass spectrometry, and ultraviolet-visible spectrophotometry. They were also evaluated for their antioxidant and antimicrobial activities using the 2,2-diphenyl-1-picrylhydrazyl assay and the disc diffusion method, respectively. All compounds showed weak antioxidant activity compared to ascorbic acid; the quinoline-hydrazone derivative showed the best antioxidant activity with IC 50 = 843.52 ppm, while the IC 50 value for quinoline-benzimidazole was 4784.66 ppm. All synthesized compounds have not been confirmed to be effective against Staphylococcus aureus and Escherichia coli bacteria in a concentration range of 75–1000 ppm. The bioactive compounds based on the quinoline-hydrazone and benzimidazole structures have been successfully synthesized and tested for their activity as antioxidant and antimicrobial agents.

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“…The structures of the target compounds were established based on elemental analysis, IR, 1 H NMR, 13 C NMR, and MS data. The starting compounds, 2-(4-(dimethylamino)styryl)-6-substituted quinoline-4-carboxylic acids 3a,b, were prepared through the Pfitzinger reaction, which offers a very convenient synthetic entry to the quinoline-4-carboxylic acid derivatives 3a,b by heating 4-(4-(dimethylamino)phenyl)but-3-en-2-one (1) and 5substituted isatins 2a,b in an aqueous/alcoholic KOH solution (Scheme 1) [55][56][57] . The condensation of quinoline-4-carboxylic acids 3a,b with thiosemicarbazide in the presence of phosphorus oxychloride 58 afforded the 2-amino-1,3,4-thiadiazoles 4a,b (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of 2-styrylquinolines as antitumour agents and EGFR kinase inhibitors: molecular docking study

El‐Sayed

El-Husseiny

Abdel-Aziz

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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A new series of 4,6-disubstituted 2-(4-(dimethylamino)styryl)quinoline 4a,b-9a,b was synthesized by the reaction of 2-(4-(dimethylamino)styryl)-6-substituted quinoline-4-carboxylic acids 3a,b with thiosemicarbazide, p-hydroxybenzaldehyde, ethylcyanoacetate, and 2,4-pentandione. In addition, the antitumour activity of all synthesized compounds 3a,b-9a,b was studied via MTT assay against two cancer cell lines (HepG2 and HCT116). Furthermore, epidermal growth factor receptor (EGFR) inhibition, using the most potent antitumour compounds, 3a, 3b, 4a, 4b, and 8a, was evaluated. The interpretation of the results showed clearly that the derivatives 3a, 4a, and 4b exhibited the highest antitumour activities against the tested cell lines HepG2 and HCT116 with IC range of 7.7-14.2 µg/ml, in comparison with the reference drugs 5-fluorouracil (IC = 7.9 and 5.3 µg/ml, respectively) and afatinib (IC = 5.4 and 11.4 µg/ml, respectively). In vitro EGFR screening showed that compounds 3a, 3b, 4a, 4b, and 8a exhibited moderate inhibition towards EGFR with IC values at micromolar levels (IC range of 16.01-1.11 µM) compared with the reference drugs sorafenib (IC = 1.14 µM) and erlotinib (IC = 0.1 µM). Molecular docking was performed to study the mode of interaction of compounds 3a and 4b with EGFR kinase.

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Synthesis of new 2- and 3-hydroxyquinoline-4-carboxylic acid derivatives as potential antioxidants

Cited by 11 publications

References 27 publications

Actinomycetes from the Red Sea Sponge Coscinoderma mathewsi: Isolation, Diversity, and Potential for Bioactive Compounds Discovery

Actinomycetes from the Red Sea Sponge Coscinoderma mathewsi: Isolation, Diversity, and Potential for Bioactive Compounds Discovery

Synthesis of antioxidant and antimicrobial bioactive compounds based on the quinoline-hydrazone and benzimidazole structure

Synthesis and biological evaluation of 2-styrylquinolines as antitumour agents and EGFR kinase inhibitors: molecular docking study

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