Antinociceptive pyrimidine derivatives: aqueous multicomponent microwave assisted synthesis

Xavier, Augusto L.; Simas, Alfredo M.; Falcão, Emerson Peter da Silva; Anjos, Janaína V. dos

doi:10.1016/j.tetlet.2013.04.099

Cited by 32 publications

(17 citation statements)

References 24 publications

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“…There are, possibly, two subsequent reactions occurring in the reaction media in order to build the heterocycle scaffold: the first one is the Knoevenagel reaction, 29 where an aldehyde reacts with ethyl cyanoacetate, to form Michael's intermediate. This latter can now react with 2-methyl-2-thiopseudourea.…”

Section: Resultsmentioning

confidence: 99%

Vasoactive Thiomethyl-Pyrimidines: Promising Drug Candidates with Vascular Activity

Andrade¹,

Araújo²,

Barbosa³

et al. 2016

J. Braz. Chem. Soc.

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Pyrimidines and their derivatives are present in various biologically active molecules. Most of the synthetic methods employed to achieve the pyrimidinone ring consist of two stages: the synthesis of a Michael intermediate from an aldehyde and an "active methylene" containing compound; and the condensation of this intermediate with a molecule containing an uranium moiety. This may take one to two days of laboratory work. In this paper we describe a new methodology in which these derivatives are obtained via multicomponent synthesis mediated by ultrasound in only 2 hours. In order to obtain water-soluble pyrimidinone derivatives, our previous compounds were further converted into their sodium salts. In pharmacologic studies, these salts inhibited phenylephrineinduced contraction in isolated rat aorta, suggesting that they may act as alpha-1 antagonists and, therefore, are candidates for anti-hypertensive drugs.

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Section: Resultsmentioning

confidence: 99%

Vasoactive Thiomethyl-Pyrimidines: Promising Drug Candidates with Vascular Activity

Andrade¹,

Araújo²,

Barbosa³

et al. 2016

J. Braz. Chem. Soc.

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“…Contributing to this need, dos Anjos et al [73] reported a basecatalyzed three-component reaction between aromatic aldehydes 5, ethyl cyanoacetate (73) (active methylene group) and benzamidine (74) in aqueous media for the construction of substituted pyrimidinones 75 under microwave irradiation (Scheme 26). The study of the protocol on a conventional system directed a reduced yield of mere 18% in 16 h. A slight variation to the protocol with malononitrile (51) as the active methylene compound affords a series of substituted 4-aminopyrimidines 76 in moderate yields.…”

Section: Pyrimidinesmentioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

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Microwave-assisted (MWA) multicomponent reactions (MCRs) have successfully emerged as one of the useful tools in the synthesis of biologically relevant heterocycles. These reactions are strategically employed for the generation of a variety of heterocycles along with multiple point diversifications. Over the last few decades classical MCRs such as Ugi, Biginelli, etc. have witnessed enhanced yield and efficiency with microwave assistance. The highlights of MWA-MCRs are high yields, reduced reaction time, selectivity, atom economy and simpler purification techniques, such an approach can accelerate the drug discovery process. The present review focuses on the recent advances in MWA-MCRs and their mechanistic insights over the past decade and shed light on its advantage over the conventional approach.

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“…4 Among the wide range of compounds tested as potential anticancer agents, pyrimidine and fused pyrimidine derivatives comprise an important class of therapeutic agents. They were reported as antitumor, [5][6][7][8][9][10] antimicrobial, 11,12 antiinflammatory, 13 anti HIV, 14 antinociceptive, 15,16 and antioxidant agents. 17,18 Various drugs containing pyrimidine nucleus were synthesized and used as anticancer agents like 5-fluorouracil (5-FU), tegafur and thioguanine ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitumor Evaluation of Novel Dihydropyrimidine, Thiazolo[3,2-a]Pyrimidine and Pyrano[2,3-d]Pyrimidine Derivatives

Abdo¹

2015

ACSi

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A simple and efficient method has been developed for the synthesis of 4,5-dihydro-2-mercapto-4-oxo-6-substituted arylpyrimidine derivatives 2a-e and their fused rings 3b, 4b, 5b, 6b and also 1,4-dihydro-2-mercaptopyrimidine derivatives 7a-e, 9a-e using triethylamine as a catalyst. The structure of the newly synthesized compounds was confirmed on the basis of their spectral data and elemental analyses. All the synthesized compounds were evaluated for their in vitro anticancer activity against six human cancer cell lines and normal fibroblasts. Nine of the tested compounds (i.e. 2a, 2c, 2d, 3b, 4b, 5b, 8, 9a and 9c) exhibited significant cytotoxicity against most cell lines. Among these derivatives compounds 2a, 3b and 9c are the most potent, they exhibited cytotoxic effect against the six cancer cell lines with IC 50 values < 330 nM compared to the standard CHS 828. Normal fibroblast cells (WI38) were affected to a much lesser extent (IC 50 >10,000 nM). Toxicity of the most potent compounds was measured against shrimp larvae; the results showed that compounds 2a and 3b are not toxic towards the tested organisms.

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Antinociceptive pyrimidine derivatives: aqueous multicomponent microwave assisted synthesis

Cited by 32 publications

References 24 publications

Vasoactive Thiomethyl-Pyrimidines: Promising Drug Candidates with Vascular Activity

Vasoactive Thiomethyl-Pyrimidines: Promising Drug Candidates with Vascular Activity

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Synthesis and Antitumor Evaluation of Novel Dihydropyrimidine, Thiazolo[3,2-a]Pyrimidine and Pyrano[2,3-d]Pyrimidine Derivatives

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