Novel chromeno [2,3-b]-pyrimidine derivatives as potential anti-microbial agents

Sankappa, U.; Isloor, Arun M.; Shetty, Prakash; Vijesh, A. M.; Prabhu, Nithin; Isloor, Shrikrishna; Thiageeswaran, M.; Fun, Hoong‐Kun

doi:10.1016/j.ejmech.2010.02.040

Cited by 50 publications

(9 citation statements)

References 15 publications

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“…In the recent years, the synthesis of novel pyranopyrimidine derivatives has gained renewed interest in the area of medicinal chemistry for their wide range of biological activities including antitumor, antitubercular, anti‐inflammatory, antihistamine, antimalarial, antigenic, antiviral, antimicrobial, [ ][ ] antiplatelet and hepatoprotective properties. Some of these compounds have also identified as new HA14‐1 analogs .…”

Section: Introductionmentioning

confidence: 99%

“…In the recent years, the synthesis of novel pyranopyrimidine derivatives has gained renewed interest in the area of medicinal chemistry for their wide range of biological activities including antitumor, [5] antitubercular, [6] anti-inflammatory, [7] antihistamine, [8] antimalarial, [9] antigenic, [10] antiviral, [11] antimicrobial, [12] [13] antiplatelet [14] DOI: 10.1002/cbdv.201800101 Chem. Biodiversity 2018, 15, e18000101 © 2018 Wiley-VHCA AG, Zurich, Switzerland (1 of 13) e18000101 and hepatoprotective [15] properties.…”

Section: Introductionmentioning

confidence: 99%

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1,2,3‐Triazole Tagged 3H‐Pyrano[2,3‐d]pyrimidine‐6‐carboxylate Derivatives: Synthesis, in Vitro Cytotoxicity, Molecular Docking and DNA Interaction Studies

Boda

Pishka

Lakshmi

et al. 2018

Chemistry & Biodiversity

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A series of novel ethyl 2,7-dimethyl-4-oxo-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-4,5-dihydro-3H-pyrano[2,3-d]pyrimidine-6-carboxylate derivatives 7a - 7m were efficiently synthesized employing click chemistry approach and evaluated for in vitro cytotoxic activity against four tumor cell lines: A549 (human lung adenocarcinoma cell line), HepG2 (human hematoma), MCF-7 (human breast adenocarcinoma), and SKOV3 (human ovarian carcinoma cell line). Among the compounds tested, the compounds 7a, 7b, 7f, 7l, and 7m have shown potential and selective activity against human lung adenocarcinoma cell line (A549) with IC ranging from 0.69 to 6.74 μm. Molecular docking studies revealed that the compounds 7a, 7b, 7f, 7l, and 7m are potent inhibitors of human DNA topoisomerase-II and also showed compliance with stranded parameters of drug likeness. The calculated binding constants, k , from UV/VIS absorptional binding studies of 7a and 7l with CT-DNA were 10.77 × 10 , 6.48 × 10 , respectively. Viscosity measurements revealed that the binding could be surface binding mainly due to groove binding. DNA cleavage study showed that 7a and 7l have the potential to cleave pBR322 plasmid DNA without any external agents.

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Section: Introductionmentioning

confidence: 99%

“…In the recent years, the synthesis of novel pyranopyrimidine derivatives has gained renewed interest in the area of medicinal chemistry for their wide range of biological activities including antitumor, [5] antitubercular, [6] anti-inflammatory, [7] antihistamine, [8] antimalarial, [9] antigenic, [10] antiviral, [11] antimicrobial, [12] [13] antiplatelet [14] DOI: 10.1002/cbdv.201800101 Chem. Biodiversity 2018, 15, e18000101 © 2018 Wiley-VHCA AG, Zurich, Switzerland (1 of 13) e18000101 and hepatoprotective [15] properties.…”

Section: Introductionmentioning

confidence: 99%

1,2,3‐Triazole Tagged 3H‐Pyrano[2,3‐d]pyrimidine‐6‐carboxylate Derivatives: Synthesis, in Vitro Cytotoxicity, Molecular Docking and DNA Interaction Studies

Boda

Pishka

Lakshmi

et al. 2018

Chemistry & Biodiversity

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“…Polyfunctionalized 4H-pyran derivative exhibits antibacterial and anti-cancer activity, is an inhibitor of EAAT1 [3] and their fused derivatives, pyranopyrimidines, are important synthetic bioactive compounds. In the recent years the synthesis of pyranopyrimidine derivatives gained renewed interest in the field of medicinal chemistry for their wide range of biological activity including antiplatelet [4], antiviral [5], antimicrobial [6,7], antimalarial [8], antigenic [9], antitumor [10], anti-inflammatory [11], antihistamine [12], ect. properties.…”

Section: Introductionmentioning

confidence: 99%

<strong>SYNTHESIS OF 2-AMINO-4<em>H</em>-PYRAN-3-CARBONITRILES ITS REACTION WITH CHLOROACETYL CHLORIDE</strong>

Hai

Thành²,

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Some 2-amino-4-aryl-3-cyano-5-ethoxycarbonyl-6-methyl-4H-pyrans were synthesized by reaction of by using three-component reaction included ethyl acetoacetate, malononitrile and appropriate substituted benzaldehydes. The role of different catalysts was examined, including organic and inorganic substances and ionic liquids. Some 2-amino-4Hpyran-3-carbonitriles were converted by reacting to chloroacetyl chloride. The structures of the obtained compounds were confirmed by the modern spectroscopic methods (IR, 1 H NMR, 13 C NMR).

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“…Numerous antitumor chemical drugs have been widely synthesized, including the chromenopyrimidines, which present interesting biological activities. The authors, who have contributed in the past to the exploration of this research topic, were interested in expanding their work by developing a facile synthesis of new derivatives and then test their antimicrobial, cytotoxicity activities [ 1 , 2 , 3 ], and in vitro antitubercular activity [ 4 ], in addition to antitumour activity. It was reported that pyrimidotriazines themselves posses biological activities with a wide range of applications [ 5 , 6 , 7 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

Badrey

Gomha

2012

Molecules

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A number of interesting heterocycles were prepared through interaction of the intermediate 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno-[2,3-d]pyrimidine (1) and reagents such as hydrazonyl halides 2 to furnish triazine derivatives 4a–l. Reaction of 1 with phenacyl bromide afforded compound 5. Moreover, the title compound 1 was subjected to condensation with active methylene compounds (ethyl acetoacetate and ethyl benzoylacetate) to give triazipinones 8a,b. The condensation with aromatic aldehydes afforded either the triazole derivatives 10a–d or Schiff base 11. In addition, the behaviour of compound 1 towards activated unsaturated compounds namely dimethyl acetylene dicarboxylate and ethoxymethylenemalonitrile was studied and it was found to furnish the triazine 13 and triazepine derivative 15, respectively. Combination of title compound 1 with chlorinated active methylene compounds delivered the triazine derivatives 18a–c. Reaction of 1 with chloroacetonitrile furnished compound 20. The structures of the products were elucidated based on their microanalyses and spectroscopic data. Finally, the antitumor activity of the new compounds 4a and 8a against human breast cell MCF-7 line and liver carcinoma cell line HepG2 were recorded.

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Novel chromeno [2,3-b]-pyrimidine derivatives as potential anti-microbial agents

Cited by 50 publications

References 15 publications

1,2,3‐Triazole Tagged 3H‐Pyrano[2,3‐d]pyrimidine‐6‐carboxylate Derivatives: Synthesis, in Vitro Cytotoxicity, Molecular Docking and DNA Interaction Studies

1,2,3‐Triazole Tagged 3H‐Pyrano[2,3‐d]pyrimidine‐6‐carboxylate Derivatives: Synthesis, in Vitro Cytotoxicity, Molecular Docking and DNA Interaction Studies

<strong>SYNTHESIS OF 2-AMINO-4<em>H</em>-PYRAN-3-CARBONITRILES ITS REACTION WITH CHLOROACETYL CHLORIDE</strong>

3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

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