New HA 14-1 analogues: synthesis of 2-amino-4-cyano-4H-chromenes

Moafi, Leila; Ahadi, Somayeh; Bazgir, Ayoob

doi:10.1016/j.tetlet.2010.09.090

Cited by 61 publications

(20 citation statements)

References 28 publications

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“…An examination of the literature revealed that pyrimidine groups exhibit a wide range of biological and pharmacological activities ,. Owing to the intense interest in the biological activity of these compounds in recent years, numerous synthetic procedures for preparing pyrimidine derivatives have been reported ,. The reported pyrimidine‐fused heterocycle synthesis requires microwave or sonication techniques and use of various catalysts such as p‐toluenesulfonic acid, diammonium hydrogen phosphate, and 1,4‐diazabicyclo[2.2.2]octane (DABCO) .…”

Section: Resultsmentioning

confidence: 99%

Catalyst‐Free Synthesis of Xanthene and Pyrimidine‐Fused Heterocyclic Derivatives at Water‐Ethanol Medium and Their Antioxidant Properties

et al. 2019

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Water‐ethanol (1:1 v/v) reaction medium has been demonstrated to be an efficient system for the catalyst‐free synthesis of biologically potent xanthene and pyrimidine‐fused heterocyclic derivatives at 60 °C. Reactions of various substituted benzaldehydes or salicylaldehydes with dimedone or barbituric acid in water‐ethanol yield corresponding xanthene and pyrimidine‐fused heterocyclic derivatives, respectively, in good yields (90−93%) within a short time frame (1−2 h). This synthetic protocol is eco‐friendly and economically viable and has a facile workup procedure and a wide scope. The synthesized compounds were screened for their antioxidant activities against 2,2‐diphenyl‐1‐picryl hydrazyl (DPPH) and ferric‐reducing antioxidant power (FRAP) assays. Compounds 13 and 23 are excellent free radical scavengers toward DPPH free radicals and compounds 12 and 23 show good activities in FRAP assay compared with standard Vitamin C.

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Section: Resultsmentioning

confidence: 99%

Catalyst‐Free Synthesis of Xanthene and Pyrimidine‐Fused Heterocyclic Derivatives at Water‐Ethanol Medium and Their Antioxidant Properties

et al. 2019

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“…In this respect, although numerous organocatalyzed racemic syntheses of this family of compounds can be found in the literature [22][23][24][25][26][27][28][29][30][31][32][33], only scarce examples following an enantioselective approach have been reported to date [34].…”

Section: Figurementioning

confidence: 99%

Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives

2015

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Abstract:The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis is a discipline in expansion that is already recognized as a well-established tool for obtaining enantiomerically enriched compounds. This review covers the particular case of the asymmetric synthesis of 2-amino-3-cyano-4H-chromenes using organocatalysis. Herein, we show the most illustrative examples of the methods developed by diverse research groups, following a classification based on these five different approaches: (1) addition of naphthol compounds to substituted α,α-dicyanoolefins; (2) addition of malononitrile to substituted o-vinylphenols; (3) addition of malononitrile to N-protected o-iminophenols; (4) Michael addition of nucleophiles to 2-iminochromene derivatives; and (5) organocatalyzed formal [4+2] cycloaddition reaction. In most cases, chiral thioureas have been found to be effective catalysts to promote the synthetic processes, and generally a bifunctional mode of action has been envisioned for them. In addition, squaramides and cinchona derivatives have been occasionally used as suitable catalysts for the substrates activation.

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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 . Some well‐known pyranopyrimidine derivatives ( 1 , 2 , 3 , and 4 ) were also reported to be antimicrobial agents [ ] ( Figure ).…”

Section: Introductionmentioning

confidence: 99%

“…Some of these compounds have also identified as new HA14-1 analogs. [16] Some well-known pyranopyrimidine derivatives (1, 2, 3, and 4) were also reported to be antimicrobial agents [17 -20] (Figure 1). Similarly, nitrogenous compounds like triazole derivatives have occupied a unique position in heterocyclic chemistry.…”

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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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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New HA 14-1 analogues: synthesis of 2-amino-4-cyano-4H-chromenes

Cited by 61 publications

References 28 publications

Catalyst‐Free Synthesis of Xanthene and Pyrimidine‐Fused Heterocyclic Derivatives at Water‐Ethanol Medium and Their Antioxidant Properties

Catalyst‐Free Synthesis of Xanthene and Pyrimidine‐Fused Heterocyclic Derivatives at Water‐Ethanol Medium and Their Antioxidant Properties

Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives

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

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