Synthesis, crystal structure, ABTS radical-scavenging activity, antimicrobial and docking studies of some novel quinoline derivatives

Tabassum, Sumaiya; Kumara, T.H. Suresha; Jasinski, Jerry P.; Millikan, Sean P.; Yathirajan, H. S.; Ganapathy, PS; Sowmya, H.B.V.; More, Sunil S.; Nagendrappa, Gopalpur; Kaur, Manpreet; Jose, Gilish

doi:10.1016/j.molstruc.2014.04.009

Cited by 24 publications

(18 citation statements)

References 66 publications

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“…The influence of concentration of the antioxidant and duration of reaction on the radical cation absorption inhibition are taken into account for antioxidant activity evaluation [ 33 ]. The antioxidants produce a discoloration with a decrease in the absorbance measured at 734 nm [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester

Panzariu

Apotrosoaei

Vasincu

et al. 2016

Chemistry Central Journal

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Backgroundl-Arginine is a semi-essential aminoacid with important role in regulation of physiological processes in humans. It serves as precursor for the synthesis of proteins and is also substrate for different enzymes such as nitric oxide synthase. This amino-acid act as free radical scavenger, inhibits the activity of pro-oxidant enzymes and thus acts as an antioxidant and has also bactericidal effect against a broad spectrum of bacteria.Results New thiazolidine-4-one derivatives of nitro-l-arginine methyl ester (NO2-Arg-OMe) have been synthesized and biologically evaluated in terms of antioxidant and antibacterial/antifungal activity. The structures of the synthesized compounds were confirmed by 1H, 13C NMR, Mass and IR spectral data. The antioxidant potential was investigated using in vitro methods based on ferric/phosphomolybdenum reducing antioxidant power and DPPH/ABTS radical scavenging assay. The antibacterial effect was investigated against Gram positive (Staphylococcus aureus ATCC 25923, Sarcina lutea ATCC 9341) and Gram negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacterial strains. The antifungal activity was also investigated against Candida spp. (Candida albicans ATCC 10231, Candida glabrata ATCC MYA 2950, Candida parapsilosis ATCC 22019).ConclusionsSynthesized compounds showed a good antioxidant activity in comparison with the NO2-Arg-OMe. The antimicrobial results support the selectivity of tested compounds especially on P. aeruginosa as bacterial strain and C. parapsilosis as fungal strain. The most proper compounds were 6g (R = 3-OCH3) and 6h (R = 2-OCH3) which showed a high free radical (DPPH, ABTS) scavenging ability and 6j (R = 2-NO2) that was the most active on both bacterial and fungal strains and also it showed the highest ABTS radical scavenging ability.Graphical abstract1: ethyl 3-aminopropionate hydrochloride, 2a–j: aromatic aldehydes, 3: thioglycolic acid, 4a–j: thiazolidine-propionic acid derivatives , 5: Nω-nitro-L-arginine methyl ester hydrochloride, 6a–j: thiazolidine-propionyl-nitro-L-arginine methyl ester derivatives

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester

Panzariu

Apotrosoaei

Vasincu

et al. 2016

Chemistry Central Journal

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“…The synthesis, reactions and biological applications of 2-chloroquinoline-3-carbaldehydes have been reviewed (Abdel-Wahab et al, 2012), and the structure of a simple reduction product (2-chloroquinolin-3yl)methanol, derived from the parent 2-chloroquinoline-3carbaldehyde, has been reported (Hathwar et al, 2010). The structures of two related esters, [(2-chloroquinolin-3-yl)methyl acetate and (2-chloro-6-methylquinolin-3-yl)methyl acetate], have also been reported recently along with a study of their radical-scavenging and antimicrobial activities ISSN 2056-9890 (Tabassum et al, 2014). Here we report the structures of five related ethers, namely methyl 5-bromo-2-[(2-chloroquinolin-3-yl)methoxy]benzoate, (I) ( Fig.…”

Section: Chemical Contextmentioning

confidence: 97%

“…In the esters (2-choloroquinolin-3-yl)methyl acetate and (2-chloro-6-methylquinolin-3-yl)methyl acetate (Tabassum et al, 2014), there are no strong hydrogen bond donors: in the methylated compound, where Z 0 = 2, the only hydrogen bond, of C-HÁ Á ÁO type, links the two independent molecules, while in the unmethylated compound, the molecules are linked into C(5) chains by C-HÁ Á ÁN hydrogen bonds. In the structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline (Chandrika et al, 2015), there are no hydrogen bonds of any kind.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of five (2-chloroquinolin-3-yl)methyl ethers: supramolecular assembly in one and two dimensions mediated by hydrogen bonding and π–π stacking

et al. 2015

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“…ABTS + , which is a blue chromophore, is generated by the reaction between 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) and ammonium persulfate. The antioxidant compound produces a discoloration of the solution with a decrease in the absorbance measured at 734 nm [28]. The ABTS radical scavenging ability (%) of samples at concentrations of 200 µg/mL is presented in Tables 6 and 7.…”

Section: Abts Radical Scavenging Assaymentioning

confidence: 99%

“…The mixture was left at room temperature for 16 h in the dark as described in [28]. The intensely colored ABTS + radical cation solution was diluted with ethanol to obtain an absorbance value of 0.7 ± 0.02 at 734 nm.…”

Section: Abts Radical Scavenging Assaymentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

et al. 2014

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New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1 H-NMR, 13 C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

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Synthesis, crystal structure, ABTS radical-scavenging activity, antimicrobial and docking studies of some novel quinoline derivatives

Cited by 24 publications

References 66 publications

Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester

Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester

Crystal structures of five (2-chloroquinolin-3-yl)methyl ethers: supramolecular assembly in one and two dimensions mediated by hydrogen bonding and π–π stacking

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

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