ChemInform Abstract: Three Component One‐Pot Synthesis of β‐Amino Ketones Mediated by (Bromodimethyl)sulfonium Bromide.

Shailaja, M.; Manjula, A.; Rao, B. Appa

doi:10.1002/chin.201037079

Cited by 4 publications

(7 citation statements)

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“…In this regard, synthetic β‐aminoketones, which is a Mannich base derivative formed in the reaction of an amine, formaldehyde (or an aldehyde), and a carbon acid, have a great potential to be candidates for industrial and medicinal applications. The Mannich reaction has been one of the classical methods for the construction of nitrogenous compounds especially β‐aminocarbonyl compounds that are versatile intermediates for the synthesis of β‐amino alcohols and acids, which have a great deal of biological significance 12. β‐Aminocarbonyl derivatives are an important class of aromatic compounds that occur in various pharmaceuticals, natural products, and versatile synthetic intermediates 13,14, and recent studies showed important biological properties of aminoketone derivatives including antitubercular, antifungal, antimalarial, antidiabetic, anti‐inflammatory, and antitumor activities 15–18.…”

Section: Discussionmentioning

confidence: 99%

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Antigenotoxic properties of two newly synthesized β‐aminoketones against N‐methyl‐N′‐nitro‐N‐nitrosoguanidine and 9‐aminoacridine‐induced mutagenesis

Öztürkcan

Turhan

Turgut

et al. 2012

J Biochem & Molecular Tox

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The aim of this study was to determine the antigenotoxic potential of two newly synthesized β-aminoketones against N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) and 9-aminoacridine (9-AA)-induced mutagenesis. The mutant bacterial tester strains were MNNG-sensitive Escherichia coli WP2 uvrA and 9-AA-sensitive Salmonella typhimurium TA1537. Both test compounds showed significant antimutagenic activity at various tested concentrations. The inhibition rates ranged from 29.5% (compound 1: 2 mM/plate) to 47.5% (compound 2: 1.5 mM/plate) for MNNG and from 25.0% (compound 2: 1 mM/plate) to 52.1% (compound 2: 2.5 mM/plate) for 9-AA genotoxicity. Moreover, the mutagenicity of the test compounds was investigated by using the same strains. Neither test compound has mutagenic properties on the bacterial strains at the tested concentrations. Thus, the findings of the present study give valuable information about chemical prevention from MNNG and 9-AA genotoxicity by using synthetic β-aminoketones.

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Section: Discussionmentioning

confidence: 99%

“…β‐Aminoketones, also known as Mannich base derivatives, are important heterocyclic compounds. Owing to various effects on living organisms, there has been a growing interest in the synthesis of novel β‐aminoketones and determination of their biological activities 12–18.…”

Section: Introductionmentioning

confidence: 99%

Antigenotoxic properties of two newly synthesized β‐aminoketones against N‐methyl‐N′‐nitro‐N‐nitrosoguanidine and 9‐aminoacridine‐induced mutagenesis

Öztürkcan

Turhan

Turgut

et al. 2012

J Biochem & Molecular Tox

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“…(°C)m.p. from ref (°C) MB1 ICl90159–160— MB2 IH88161–163— MB3 IF84156–157— MB4 HH91167–169168–170 [20,42,43] MB5 HCl91167–168169–171 [20,42–44] MB6 HF87164–166163–164 [42] MB7 HCH 3 85167–168169–171 [20,42–44] MB8 HOCH 3 78168–169166–169 [42,44] MB9 ICH 3 82160–161— MB10 IOCH 3 75150–151—without catalystHHn.r.——…”

Section: Resultsmentioning

confidence: 99%

“…The resolution of the scanning was 4.0 cm −1 at 16 scans. Melting points were determined on a Mel-Temp capillary melting points apparatus, model 1001, and obtained values are compared to those available in the literature for known compounds [42–44]. Elemental microanalyses for carbon, hydrogen and nitrogen were performed at the Faculty of Chemistry, University of Belgrade.…”

Section: Methodsmentioning

confidence: 99%

Acetophenone Mannich bases: study of ionic liquid catalysed synthesis and antioxidative potential of products

et al. 2018

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Three-component Mannich reaction of acetophenone or 4-iodoacetophenone with a variety of substituted anilines and benzaldehyde, catalysed with diethanolammonium chloroacetate, was performed under mild conditions. Mannich bases (MBs), of which five are new, were obtained in good to excellent yields. All compounds were characterized using elemental analysis, NMR and IR. In addition, detailed experimental and simulated UV–Vis spectral characterization of these compounds is presented here for the first time. In vitro antioxidative potential of synthetized MBs was evaluated using 2,2-diphenyl-1-picryl-hydrazyl radical and density functional theory (DFT) thermodynamical study. It was shown that compounds with anisidine moiety express moderate antioxidative activity. Mechanism of the organocatalysed Mannich reaction was thoroughly inspected by means of DFT. The reaction undergoes the hydrogen bonding-assisted mechanism. Moreover, the proposed rate determining step of the overall reaction is water elimination in the process of iminium ion formation. To the extent of our knowledge, this is the first detailed report on the influence of this type of catalyst on the formation of iminium ion, as a crucial intermediate for the whole reaction.

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“…The first investigated group was mannich bases. Mannich reaction is one of the classical methods for the construction of nitrogenous compounds especially β-amino carbonyl compounds that are versatile intermediates for the synthesis of β-amino alcohols and acids, which have remarkable biological significance (Shailaja et al, 2010). β-aminocarbonyl derivatives are an important class of heterocyclic compounds that occur in various pharmaceuticals, natural products and versatile synthetic intermediates (Tramontini and Angiolini, 1990; Yi et al, 1991).…”

Section: Discussionmentioning

confidence: 99%

Protective properties of five newly synthesized cyclic compounds against sodium azide and N-methyl-N′-nitro-N-nitrosoguanidine genotoxicity

et al. 2011

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The current study aims to determine the antimutagenic potential of five newly synthesized cyclic compounds against the genotoxic agents sodium azide (NaN₃) and N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). The mutant bacterial tester strains were NaN₃-sensitive Salmonella typhimurium TA1535 and MNNG-sensitive Escherichia coli WP2uvrA. According to the results, all the test compounds showed significant antimutagenic activity. The inhibition rates ranged from 26.05% (Compound 4-1 µg/plate) to 68.54% (Compound 5-0.01 µg/plate) for NaN₃ and from 32.44% (Compound 3-1 µg/plate) to 60.77% (Compound 5-1 µg/plate) for MNNG genotoxicity. Moreover, the mutagenic potential of the test compounds was investigated using the same strains. The results showed that all the test compounds do not have mutagenic potential on the bacterial strains at the tested concentrations. Thus, the findings of the present study give valuable information about chemical prevention from NaN₃ and MNNG genotoxicity.

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ChemInform Abstract: Three Component One‐Pot Synthesis of β‐Amino Ketones Mediated by (Bromodimethyl)sulfonium Bromide.

Cited by 4 publications

References 0 publications

Antigenotoxic properties of two newly synthesized β‐aminoketones against N‐methyl‐N′‐nitro‐N‐nitrosoguanidine and 9‐aminoacridine‐induced mutagenesis

Antigenotoxic properties of two newly synthesized β‐aminoketones against N‐methyl‐N′‐nitro‐N‐nitrosoguanidine and 9‐aminoacridine‐induced mutagenesis

Acetophenone Mannich bases: study of ionic liquid catalysed synthesis and antioxidative potential of products

Protective properties of five newly synthesized cyclic compounds against sodium azide and N-methyl-N′-nitro-N-nitrosoguanidine genotoxicity

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