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      Synthesis of Some Novel Chromenopyrimidine Derivatives and Evaluation of Their Biological Activities

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          Abstract

          Pyrimidine nucleosides are constituents of fundamental structure of the cells. There has been considerable attentions in the chemistry of pyrimidine derivatives due to having a wide range of biological activities such as antiviral, anti-malarial agents, cytostatic, antithelemintic, antibacterial, adenosine receptor ligands, anti-cancer agents, compounds targeting delayed-type hypersensivity and anti-convulsant agents. As a part of our research work in the synthesis of pyrimidines containing biological activities, a series of chromenopyrimidine derivatives were synthesized by reaction of an intermediate imine and ammonia derivatives in good to high yields. All synthesized compounds were characterized using IR and NMR ( 1H and 13C) spectroscopy and elemental analysis data. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia Coli (ATCC, 35922).

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          Most cited references59

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          Pyrimidine as constituent of natural biologically active compounds.

          This review describes the various manifestations of the pyrimidine system (alkylated, glycosylated, benzo-annelated.). These comprise pyrimidine nucleosides as well as alkaloids and antibiotics--some of them have been discovered and isolated from natural sources already long time ago, others have been reported very recently. A short overview on pyrimidine syntheses (prebiotic synthesis, biosynthesis, and metabolism) is given. The biological activities of most of the pyrimidine analogs are briefly described, and, in some cases, syntheses are formulated.
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            Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives.

            Sixteen new 2-benzylidene-7-methyl-3-oxo-5-(substituted phenyl)-2, 3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid methyl esters (1a-4d) have been synthesized by reacting 1,2,3,4-tetrahydropyrimidine-2-thiones (1-4) with chloroacetic acid and appropriate benzaldehydes in a single step. Their structures have been proved by IR, 1H NMR, mass spectra and elemental analysis. The compounds were tested for their anti-inflammatory activities. Test results revealed that compounds 1b, 1c, 4a and 4c exerted moderate anti-inflammatory activity at the 100 mg/kg dose level compared with indomethacin.
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              An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by a ZnCl(2)-catalyzed three-component coupling reaction.

              We have developed a ZnCl(2)-catalyzed three-component coupling reaction involving a variety of functionalized enamines, triethyl orthoformate, and ammonium acetate, which leads to the production of 4,5-disubstituted pyrimidine derivatives in a single step. The procedure can be successfully applied to the efficient synthesis of mono- and disubstituted pyrimidine derivatives, using methyl ketone derivatives instead of enamines.
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                Author and article information

                Journal
                Iran J Pharm Res
                Iran J Pharm Res
                IJPR
                Iranian Journal of Pharmaceutical Research : IJPR
                Shaheed Beheshti University of Medical Sciences (Tehran, Iran )
                1735-0328
                1726-6890
                Summer 2014
                : 13
                : 3
                : 873-879
                Affiliations
                [a ] Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran.
                [b ] Faculty of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran.
                [c ] Department of Biology, Arak University, Arak 38156-8-8349, Iran.
                Author notes
                [* ]Corresponding author: E-mail: akbar_mobini@yahoo.com
                Article
                ijpr-13-873
                4177647
                25276187
                2ca0dfec-b9b7-4ba4-9339-84684d00e96e
                © 2014 by School of Pharmacy, Shaheed Beheshti University of Medical Sciences and Health Services

                This is an Open Access article distributed under the terms of the Creative Commons Attribution License, ( http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                : January 2013
                : April 2013
                Categories
                Original Article

                imine,chromenopyrimidine,pyranopyrimidine,antibacterial,multicomponent

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