Synthesis of quinoline/naphthalene-containing azaphenothiazines and their potent in vitro antioxidant properties

Jeleń, Małgorzata; Bavavea, Eugenia I.; Παππά, Μαρία; Kourounakis, Angeliki P.; Morak‐Młodawska, Beata; Pluta, Krystian

doi:10.1007/s00044-014-1247-y

Cited by 30 publications

(14 citation statements)

References 26 publications

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“…This result suggests that these phenothiazine compounds can prevent or minimize lipid peroxidation or cell damaged caused by free radicals. Similarly, tetracyclic NH-azaphenothiazines were shown to exhibit significant antioxidant activity to inhibit lipid peroxidation in vitro which was suggested to be due to substitution of H, Cl, and OCH 3 on the benzene ring [ 49 ]. Thus, in this study, the decrease in in vivo lipidic peroxidation may be due to the additional benzene rings of the newly synthesized phenothiazine derivatives which promoted substitutions.…”

Section: Resultsmentioning

confidence: 99%

Potential Antioxidant Activity of New Tetracyclic and Pentacyclic Nonlinear Phenothiazine Derivatives

Engwa

Ayuk

Igbojekwe

et al. 2016

Biochemistry Research International

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The global increase in oxidative stress related diseases such as cancer, cardiovascular, and inflammatory diseases caused by overwhelming level of free radicals in the body has encouraged the search for new antioxidant agents. Based on the ability of newly synthesized phenothiazine derivatives (6-chloro-11-azabenzo[a]phenothiazine-5-one and 6-[4-bromophenyl]-10-methyl-11-azabenzo[a]phenothiazine-5-one) to oxidize H2O2, a known free radical to sulfoxide, this study assessed the in vitro and in vivo antioxidant activity. The synthesized phenothiazine derivatives exhibited reducing power potential to convert Fe3+ to Fe2+ and high ability to scavenge H2O2 free radical in vitro. These activities were comparable to ascorbic acid, a standard antioxidant. The catalase activity significantly increased (p < 0.05) in groups 1 and 2 animals that received the phenothiazine derivatives compared to the controls (groups 3 and 4) suggesting the ability of the phenothiazine derivatives to scavenge H2O2 in vivo. The malondialdehyde level in groups 1 and 2 animals was lower than that in group 3 that received the reference compound (ascorbic acid) and group 4 that received the solvent suggesting the ability of the phenothiazine derivatives to prevent lipid membrane damage. AST and bilirubin levels were higher in group 2 animals which received 6-[4-bromophenyl]-10-methyl-11-azabenzo[a]phenothiazine-5-one compared to group 3, the positive control. The results suggest that phenothiazine derivatives, especially 6-chloro-11-azabenzo[a]phenothiazine-5-one, possess antioxidant activity though 6-[4-bromophenyl]-10-methyl-11-azabenzo[a]phenothiazine-5-one was slightly toxic. This activity may be due to the presence of electron donors such as sulfur as well as the richness of hydrogen in the additional benzene rings for substitution. Further study is needed to identify tolerable doses for possible therapeutic purposes.

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Section: Resultsmentioning

confidence: 99%

Potential Antioxidant Activity of New Tetracyclic and Pentacyclic Nonlinear Phenothiazine Derivatives

Engwa

Ayuk

Igbojekwe

et al. 2016

Biochemistry Research International

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“…The generation of ROS by the metabolism of naphthalene-containing drugs makes it suitable as cancer therapeutics. 3 The naphthalene scaffold possesses various antagonistic activities and used as anticancer agents, 14 antimicrobial, 15 neurodegenerative diseases, 16 anti-inflammatory, 17 antidiabetic, 18 anticonvulsant, 19 antihypertensive, 20 antidepressant, 21 antipsychotic, 22 antitubercular, and antiviral. 23 The introduction of different functional groups on the naphthalene nucleus could provide a promising strategy to achieve various biological activities.…”

Section: Introductionmentioning

confidence: 99%

Toxicological Screening of 4-Phenyl-3,4-dihydrobenzo[h]quinolin-2(1H)-one: A New Potential Candidate for Alzheimer’s Treatment

et al. 2021

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Toxicity studies are necessary for the development of a new drug. Naphthalene is a bicyclic molecule and is easy to derivatize. In our previous study, a derivative of naphthalene (4-phenyl,3,4-dihydrobenzoquinoline-2( H )one) was synthesized and reported its in vitro activity on different enzymes. This study was a probe to investigate the toxicity potential of that compound (SF3). Acute oral (425), subacute (407), and teratogenicity (414) studies were planned according to their respective guidelines given by organization of economic cooperation and development (OECD). Acute oral, subacute, and teratogenicity studies were carried out on 2000, 5–40, and 40 mg/kg doses. Blood samples were collected for hematological and biochemical analyses. Vital organs were excised for oxidative stress (superoxide dismutase, catalase, glutathione, and malondialdehyde) and histopathological analysis. LD 50 of SF3 was higher than 2000 mg/kg. In acute and subacute studies, levels of alkaline phosphates and aspartate transaminase were increased. Teratogenicity showed no resorptions, no skeletal or soft tissue abnormalities, and no cleft pallet. Oxidative stress biomarkers were close to the normal, and no increase in the malondialdehyde level was seen. Histopathological studies revealed normal tissue architecture of the selected organs, except kidney, in acute oral and subacute toxicity studies at 40 mg/kg. The study concluded that SF3 is safer if used as a drug.

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“…The α-amylase inhibitors with a high degree of potency and specificity are still needed for the exploration of a new class of inhibitors. In this respect, several naphthalene incorporated heterocyclic compounds were synthesized and tested for their biological activities such as anticonvulsant, 25,26 antimicrobial, [27][28][29] antioxidant 30 and anticancer activity. 31,32 In view of the above observation, in our study we have synthesized naphthalene incorporated 2,4,5-trisubstituted imidazole derivatives and have screened for their antioxidant and α-amylase inhibition activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antioxidant and $$\alpha $$-amylase inhibition activity of naphthalene-containing 2,4,5-trisubstituted imidazole derivatives

2019

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A series of naphthalene ring containing 2,4,5-trisubstituted imidazole derivatives (2a-2l) were synthesized using one-pot multicomponent reaction. The reactions were carried out using naphthaldehyde and substituted benzil in the presence of ammonium acetate in acetic acid media. All newly synthesized imidazole derivatives were characterized by FT-IR, 1 H NMR, 13 C NMR and mass spectral analysis. Newly synthesized imidazole derivatives were screened for their in-vitro antioxidant activity by DPPH free radical scavenging assay method and α-amylase inhibition activity by DNS method. All the compounds showed excellent α-amylase activity at 10, 50 and 100 μg/mL and compounds 2d, 2g, 2k exhibited good antioxidant activity.

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Synthesis of quinoline/naphthalene-containing azaphenothiazines and their potent in vitro antioxidant properties

Cited by 30 publications

References 26 publications

Potential Antioxidant Activity of New Tetracyclic and Pentacyclic Nonlinear Phenothiazine Derivatives

Potential Antioxidant Activity of New Tetracyclic and Pentacyclic Nonlinear Phenothiazine Derivatives

Toxicological Screening of 4-Phenyl-3,4-dihydrobenzo[h]quinolin-2(1H)-one: A New Potential Candidate for Alzheimer’s Treatment

Synthesis, antioxidant and $$\alpha $$-amylase inhibition activity of naphthalene-containing 2,4,5-trisubstituted imidazole derivatives

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