Synthesis and in vitro evaluation of substituted pyrimido[5,4-d]pyrimidines as a novel class of Antimycobacterium tuberculosis agents

Bacelar, Ana Helena Dias; Carvalho, M. Alice; Proença, M. Fernanda

doi:10.1016/j.ejmech.2010.03.047

Cited by 40 publications

(35 citation statements)

References 27 publications

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“…Stereochemistry and conformation of PP glycoside anomers have been studied (89JME629, 90JA3622); for instance, the exocyclic NH proton resonates at lower field in b-anomers 159b and 160b compared to a-anomers 159a and 160a (see below). 43-type compounds show three exchangeable NH-protons (10EJM3234). The spectrum of PP polymer 171b has been reproduced (02MM2993).…”

Section: H-nmr Spectramentioning

confidence: 99%

Recent Progress in Pyrimido[5,4-d]pyrimidine Chemistry

Fischer¹

2015

Advances in Heterocyclic Chemistry

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Section: H-nmr Spectramentioning

confidence: 99%

Recent Progress in Pyrimido[5,4-d]pyrimidine Chemistry

Fischer¹

2015

Advances in Heterocyclic Chemistry

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“…The solid product was filtered and crystallized from dioxan to give 4 as yellowish crystals, mp 278-280°C, yield 65%; IR (ʋ cm À1 ): 3250-3143 (b, NH-NH), 2210 (C≡N), 1670, 1610 (C¼O,-CONH), 1588 (C¼N), 1392 (NCN), 1239 (C-F), 837,811 (P-substituted ring), 659 (C-F); 1 H-NMR (δ ppm): 12.38, 12.14 (each s, 2H, NH, NH of 1,2,3-triazine), 8 6a,b). A mixture of 2 (0.01 mol) and compound 5a and/or 5b [35] (0.01 mol) in NaOH (5%, 100 mL) was refluxed for 2 h then cooled and poured into ice HCl.…”

Section: -(4′-fluorophenyl)-7-cyano-12-dihydro-pyrimido[32-c] [12mentioning

confidence: 99%

“…Pyrimidines continue to receive much attention in recent years due to their unique physical, chemical, and pharmacological applications as potential microbial growth inhibitors [1][2][3], photochemical probe agents [4], and biocidal agents [5]. A variety of nitrogen-bridged pyrimidines was reported to be used as multi-targeted small molecule inhibitors and resistance-modifying agents [6][7][8][9][10][11]. On the other hand, 1,2,4-triazines and their condensed hetrobicyclic ring systems have attracted considerable interest in recent years as anti-HIV [12], antifungal agents [13,14], molluscicidal agents [15], and antitumor agents [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Studies of Fluorinated Pyrimido‐1,2,4‐Triazines: Protective Effect Against Some Plant Pathogenic Fungi

Aqlan

Makki

Abdel‐Rahman

2015

Journal of Heterocyclic Chem

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In search for new biologically active compounds, several new fluorine‐substituted pyrimido [2,3‐c][1,2,4]triazino (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16) have been synthesized via the nucleophilic attack of 2‐hydrazinopyrimidinone (2) toward more positive carbons under different conditions. Structure of the newly synthesized compounds was deduced from elemental analyses as well as their spectral data (UV, IR, NMR, and M/S). The antifungal activity of the target ring systems has been evaluated both in vitro and in vivo against some phytopathogenic fungi associated with wheat grains. Result showed that compounds 6, 7, and 8 have high protection of wheat grains against the fungal infection.

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“…They were found to be potent agents for anti-fungal [18], anti-bacterial [19], anti-inflammatory [20,21], anti-cancer [22][23][24], anti-HIV [25,26], and anti-tuberculosis activities [27,28]. The synthesized 4-hydroxy-2-methyl-6-(phenyl)pyrimidine-5-carbonitrile derivatives are also found to resemble many natural products (Fig.…”

Section: Introductionmentioning

confidence: 95%

One-pot synthesis and in vivo biological evaluation of new pyrimidine privileged scaffolds as potent anti-inflammatory agents

et al. 2015

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A simple methodology has been developed for the synthesis of diverse members of multifunctionalized 4-hydroxy-2-methyl-6-(phenyl)pyrimidine-5-carbonitrile derivatives via multicomponent reaction of aromatic aldehydes, ethyl cyanoacetate, and acetamidine hydrochloride using a quantitative amount of NaOH in dry DMF at 80°C in a single procedural step. The carbon skeleton of synthesized compounds resembles the bacimethrin, an antibiotic active against several yeast and bacteria. The anti-inflammatory activities of all the synthesized compounds were assessed on Wistar rats using diclofenac sodium as a standard reference. The compound AC1, 2, 5, 9, and AC10 showed promising anti-inflammatory activity (80-83 %) in comparison with diclofenac sodium (85 %) in the carrageenan-induced rat paw edema assay, which is the key finding of this article. Graphical Abstract The synthesized 4-hydroxy-2-methyl-6-(phenyl)pyrimidine-5-carbonitrile derivatives shown promising anti-inflammatory activity (80-83 %) in comparison with diclofenac sodium (85 %) in the carrageenan-induced rat paw edema assay.Electronic supplementary material The online version of this article (

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Synthesis and in vitro evaluation of substituted pyrimido[5,4-d]pyrimidines as a novel class of Antimycobacterium tuberculosis agents

Cited by 40 publications

References 27 publications

Recent Progress in Pyrimido[5,4-d]pyrimidine Chemistry

Recent Progress in Pyrimido[5,4-d]pyrimidine Chemistry

Synthesis, Spectroscopic Studies of Fluorinated Pyrimido‐1,2,4‐Triazines: Protective Effect Against Some Plant Pathogenic Fungi

One-pot synthesis and in vivo biological evaluation of new pyrimidine privileged scaffolds as potent anti-inflammatory agents

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