Synthesis and cytotoxic activity of novel benzopyrano[3,2-c]chromene-6,8-dione derivatives

Shafiee, Abbas; Motamedi, Radineh; Firuzi, Omidreza; Meili, Savis; Mehdipour, Ahmad Reza; Miri, Ramin

doi:10.1007/s00044-010-9340-3

Cited by 23 publications

(12 citation statements)

References 26 publications

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“…All products were identified by comparison with authentic samples. [16] These results demonstrate that both the yields and the reaction time are relatively independent of the position of the substituent in aryl aldehyde. However, nitrobenzaldehyde had relatively better yields.…”

Section: Introductionmentioning

confidence: 90%

“…[15] We have recently reported design, synthesis and toxicity effect of novel benzopyrano [3,2-c]chromene-6,8-diones 4 derivatives (Scheme 1). [16] In continuation of our attempts to develop selective and preoperatively useful methodology, using heteropolyacids as green catalysts in various organic reactions, [17] we report a rapid and convenient method for synthesis of these compounds, catalyzed by heteropolyacids (HPAs).…”

Section: Introductionmentioning

confidence: 99%

“…[16] The structures of compounds 4 were deduced from their infrared (IR) 16] Armed with our experiences using various HPAs as green catalysts in acidic catalytic reactions, [17] we were persuaded to study the use of these catalysts for synthesis of compounds 4. Initially the coupling reaction of 4-hydroxy coumarine 3, 4-nitrobenzaldehyde 2a, and 1,3-cyclohexadione 1 in ethanol with different catalytic amounts of H 6 P 2 Mo 18 O 62 and at room temperature and refluxing condition was investigated to optimize the reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Method for Synthesis of Benzopyrano[3,2-c]chromene-6,8-dione Derivatives by Heteropoly Acids

Motamedi

Baghbani

Bamoharram

2012

Synthetic Communications

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Section: Introductionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Catalytic Method for Synthesis of Benzopyrano[3,2-c]chromene-6,8-dione Derivatives by Heteropoly Acids

Motamedi

Baghbani

Bamoharram

2012

Synthetic Communications

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“…Both the pyrimidines and coumarins exhibit diverse biological properties (Kulkarni et al, 2006;Shafiee et al, 2010). It was observed that linking of these two active pharmacophores would generate novel molecular templates which are likely to exhibit interesting biological properties in animal models (Keri et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Analgesic study of novel pyrimidine derivatives linked with coumarin moiety

Gupta¹,

Sharma²,

Dudhe

et al. 2011

Med Chem Res

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A novel series of 2-amino-4-(coumarin-3-yl)-6-substituted phenyl pyrimidines (5a-h) were synthesized from 3-acetylcoumarin (3). The structures of the synthesized compounds were elucidated by I.R., 1 H NMR, 13 C NMR, and Mass spectroscopic techniques. The synthesized compounds were screened for in vivo analgesic activities at a dose of 20 mg/kg body weight (b.w). Among them, compounds 5b and 5h exhibited significant analgesic activity comparable with control as well as standard drug diclofenac sodium using acetic acid-induced writhing model.

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“…Previously we reported the synthesis and cytotoxic activity of novel coumarin derivatives, chromeno [4,3-b]-quinolines, benzopyrano [3,2-c]chromene-6,8-diones and chromeno [3',4']pyrano [2,3-b]quinoline-6,9-diones [8][9][10]. In continuation of our studies, and owing to the importance of chromenopyridines, we decided to investigate the synthesis of new 5-oxo-5H-chromeno [4,3-b]pyridine derivatives by a simple method.…”

mentioning

confidence: 99%

Solvent-free synthesis of novel 5-oxo-5H-chromeno[4,3-b]pyridine derivatives

Motamedi

2013

Chem Heterocycl Comp

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An efficient and simple method for the synthesis of new 5-oxo- 5H-chromeno[4,3-b]pyridine derivatives via Michael addition of 4-aminocoumarin to arylidenemalononitrile for 20 min at 150°C without any solvent is proposed. The advantages of this procedure are mild reaction conditions, high yields of products, and operational simplicity.Keywords: 5-oxo-5H-chromeno [4,3-b]pyridine, Michael addition, solvent-free synthesis.Various coumarin derivatives, particularly those fused with other heterocycles, have attracted much attention in recent years due to their biological activities [1,2], and encouraged research to improve the availability of these compounds with regard to procedures and substrates. Coumarins condensed to pyridine ring (chromeno[3,4-b]pyridin-5-ones) are also under investigation, as they constitute the backbone of naturally occurring alkaloids, e.g. santiagonamine [3]. Some of them, both natural and non-natural products, are currently in clinical trials [4][5][6][7].Previously we reported the synthesis and cytotoxic activity of novel coumarin derivatives, chromeno[4,3-b]-quinolines, benzopyrano[3,2-c]chromene-6,8-diones and chromeno[3',4']pyrano[2,3-b]quinoline-6,9-diones [8-10]. In continuation of our studies, and owing to the importance of chromenopyridines, we decided to investigate the synthesis of new 5-oxo-5H-chromeno[4,3-b]pyridine derivatives by a simple method.The literature data on existing synthetic routes to 5-oxo-5H-chromeno[4,3-b]pyridines can be classified based on the functionality of the starting materials. Synthetically significant approaches include multistep ring formation by reaction of 4-aminocoumarin with alkyl vinyl ketones [11], 4-amino-3-formylcoumarin with C-H acids [12], 4-chloro-3-formylcoumarin with Wittig phosphoranes [13], or 4-oxo-4H-chromene-3-carbaldehydes with enamines followed by oxidation [14]. In another procedure, 7-trifluoromethyl group-containing 5-oxo-5H-chromeno[4,3-b]pyridine derivatives were prepared by reaction of 4-chloro-3-(trifluoroacetyl)-2H-chromen-2-one and aniline followed by intramolecular cyclization in the presence of concentrated sulfuric acid [15]. However, these methods have disadvantages such as harsh reaction conditions, sensitivity of starting materials and reagents to moisture, and use of toxic reagents (POCl 3 , TMSCl) or oxidants (CrO 3 , conc. H 2 SO 4 ).In the present work, we have developed the synthesis of new 2-amino-4-aryl-5-oxo-5H-chromeno-[4,3-b]pyridine-3-carbonitriles 3a-n via Michael addition of 4-aminocoumarin (1) to arylidenemalononitrile 2a-n in 60-80% yields in a solvent-free system at 150°C.

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Synthesis and cytotoxic activity of novel benzopyrano[3,2-c]chromene-6,8-dione derivatives

Cited by 23 publications

References 26 publications

Catalytic Method for Synthesis of Benzopyrano[3,2-c]chromene-6,8-dione Derivatives by Heteropoly Acids

Catalytic Method for Synthesis of Benzopyrano[3,2-c]chromene-6,8-dione Derivatives by Heteropoly Acids

Analgesic study of novel pyrimidine derivatives linked with coumarin moiety

Solvent-free synthesis of novel 5-oxo-5H-chromeno[4,3-b]pyridine derivatives

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