Biological Activities of Eco-Friendly Synthesized Hantzsch Adducts

Pacheco, Samira R.; Braga, Taniris Cafiero; Silva, Daniel L. da; Horta, Lívia P.; Reis, Fabiano; Ruiz, Ana Lúcia Tasca Góis; Carvalho, João Ernesto de; Modolo, Luzia V.; Fátima, Ângelo de

doi:10.2174/1573406411309060014

Cited by 7 publications

(11 citation statements)

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“…In addition, further developments were made to the methodology in order to enhance the reaction yield and also to reduce the reaction time. Other recent developments involve reducing the energy and waste that is produced in the reaction for a more environmentally friendly synthesis [13][14][15][16]. The source of nitrogen has also been varied from the classical use of ammonia.…”

Section: Introductionmentioning

confidence: 99%

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

Bosica¹,

Demanuele²,

Padrón³

et al. 2020

Beilstein J. Org. Chem.

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A rapid route for obtaining unsymmetrical 1,2-dihydropyridines (1,2-DHPs) as opposed to 1,4-dihydropyridines (1,4-DHPs) has been achieved via a one-pot multicomponent Hantzsch reaction. A benign protocol has been developed for the preparation of various 1,2-dihydropyridine derivatives using heterogenized phosphotungstic acid on alumina support (40 wt %). High yields of over 75% have been accomplished in just 2–3.5 h after screening several heterogeneous catalysts and investigating the optimal reaction conditions. The catalyst chosen has passed the heterogeneity test and was shown to have the potential of being reused for up to 8 consecutive cycles before having a significant loss in activity. In addition, aromatic aldehydes gave the aforementioned regioisomer while the classical 1,4-DHPs were obtained when carrying out the reaction using aliphatic aldehydes. The preliminary study of the antiproliferative activity against human solid tumor cells demonstrated that 1,2-DHPs could inhibit cancer cell growth in the low micromolar range.

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Section: Introductionmentioning

confidence: 99%

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

Bosica¹,

Demanuele²,

Padrón³

et al. 2020

Beilstein J. Org. Chem.

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“…40 To optimise the multicomponent reaction conditions, a set of experiments was realised using stearic β-ketoester 3b as a model and sulfamic acid as the catalyst. Initially, polyhydroquinoline 12b was synthesised by reaction of 3b, benzaldehyde (6), dimedone (5) and ammonium acetate (4) in the presence of 20 mol% of H 2 NSO 3 H in methanol at reflux (Scheme 2). However, in this experimental condition, the TLC of the reaction mixture revealed the presence of starting material after four hours and the 12b was isolated in a poor yield ( Table 1, entry 1).…”

Section: Resultsmentioning

confidence: 99%

“…1,4-DHPs such as nifedipine (1) and others derivatives are well known as calcium channel blockers and have emerged as one of the most important class of drugs for the treatment of hypertension ( Figure 1). 4 This class of compounds shows a range of biological properties, such as antituberculosis, antiviral, antileishmanial, antitrypanosomal, and anticancer activities. [4][5][6][7][8] According to the literature, photoactive 2-(2'hydroxyphenyl)benzoxazole-1,4-dihydropyridine (HBO-DHP) dyads were obtained by a multicomponent Hantzsch reaction using a fluorescent aldehyde, a 1,3-dicarbonylic compound and ammonium acetate.…”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14] The method for synthesis of PHQs involves a multicomponent Hantzsch reaction of an aldehyde with cyclic 1,3-diketone, ethyl acetoacetate, and ammonia acetate in an acid catalyst. 4,15 Alternatively, the Hantzsch reaction for the synthesis of polyhydroquinolines was recently studied using crosslinked poly (AMPS-co-AA), 16 magnetic Fe 3 O 4 nanoparticles, 17 Brönsted ionic liquid, 18 [TBA] 2 [W 6 O 19 ], 19 visible light irradiation in ethyl-L-lactate-water, 20 microwave irradiation, 21 organocatalysts, 22 ZnO-beta zeolite, 23 p-TSA 24 and vanadium dodecylamino phosphate. 25 However, these methods suffer from drawbacks, such as the use of complex metal catalysts, the use of expensive reagents, difficult workup, corrosion problems, effluent pollution and nonrecoverable catalysts.…”

Section: Introductionmentioning

confidence: 99%

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Multicomponent synthesis of novel hybrid PHQ-fatty acids

et al. 2015

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Multicomponent reactions as methods for green synthesis are important pathways for obtaining of pharmacological compounds. In this work, an efficient synthesis of new fatty Hantzsch derivative compounds using a four-component reaction is described. We demonstrate for the first time a fatty acid polyhydroquinoline (hybrid PHQ-fatty acids) synthesis from renewable resources containing C16 and C18 saturated and unsaturated fatty chains, including the ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid), the major constituent of castor oil. The experimental results demonstrate that the best value for charging the sulfamic acid was 20 mol% and that thirty new hybrids PHQ-fatty acids were synthesised in good yields.

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“…In order to test if the antimutagenic effects of the AV-153-Na are due to its capability to scavenge free radicals and peroxynitrite, we have studied these effects using in vitro systems, as some 1,4-DHP are able to scavenge different reactive oxygen and nitrogen species themselves; the reactions can be observed in vitro ( Pacheco et al, 2013 ; Vijesh et al, 2011 ). Unexpectedly, it turned out that the compound does not react with peroxynitrite, and ability to scavenge hydroxyl radical turned out to be modest, thus the cause of the antimutagenic effect should have been sought inside the cells.…”

Section: Discussionmentioning

confidence: 99%

Study of interaction of antimutagenic 1,4-dihydropyridine AV-153-Na with DNA-damaging molecules and its impact on DNA repair activity

Ļeonova

Rostoka

Sauvaigo³

et al. 2018

PeerJ

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Background1,4-dihydropyridines (1,4-DHP) possesses important biochemical and pharmacological properties, including antioxidant and antimutagenic activities. It was shown that the antimutagenic 1,4-dihydropyridine AV-153-Na interacts with DNA. The aim of the current study was to test the capability of the compound to scavenge peroxynitrite and hydroxyl radical, to test intracellular distribution of the compound, and to assess the ability of the compound to modify the activity of DNA repair enzymes and to protect the DNA in living cells against peroxynitrite-induced damage.MethodsPeroxynitrite decomposition was assayed by UV spectroscopy, hydroxyl radical scavenging—by EPR spectroscopy. DNA breakage was determined by the “comet method”, activity of DNA repair enzymes—using Glyco-SPOT and ExSy-SPOT assays. Intracellular distribution of the compound was studied by laser confocal scanning fluorescence microscopy. Fluorescence spectroscopy titration and circular dichroism spectroscopy were used to study interactions of the compound with human serum albumin.ResultsSome ability to scavenge hydroxyl radical by AV-153-Na was detected by the EPR method, but it turned out to be incapable of reacting chemically with peroxynitrite. However, AV-153-Na effectively decreased DNA damage produced by peroxynitrite in cultured HeLa cells. The Glyco-SPOT test essentially revealed an inhibition by AV-153-Na of the enzymes involved thymine glycol repair. Results with ExSy-SPOT chip indicate that AV-153-Na significantly stimulates excision/synthesis repair of 8-oxoguanine (8-oxoG), abasic sites (AP sites) and alkylated bases. Laser confocal scanning fluorescence microscopy demonstrated that within the cells AV-153-Na was found mostly in the cytoplasm; however, a stain in nucleolus was also detected. Binding to cytoplasmic structures might occur due to high affinity of the compound to proteins revealed by spectroscopical methods.DiscussionActivation of DNA repair enzymes after binding to DNA appears to be the basis for the antimutagenic effects of AV-153-Na.

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Biological Activities of Eco-Friendly Synthesized Hantzsch Adducts

Cited by 7 publications

References 0 publications

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

Multicomponent synthesis of novel hybrid PHQ-fatty acids

Study of interaction of antimutagenic 1,4-dihydropyridine AV-153-Na with DNA-damaging molecules and its impact on DNA repair activity

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