Design, Synthesis and Evaluation of Cytotoxicity of Novel Chromeno[4,3‐<i>b</i>]quinoline Derivatives

Miri, Ramin; Motamedi, Radineh; Rezaei, Mohammad Reza; Firuzi, Omidreza; Javidnia, Azita; Shafiee, Abbas

doi:10.1002/ardp.201000196

Cited by 64 publications

(28 citation statements)

References 36 publications

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“…1 H NMR and mass spectra of the product were in agreement with those reported in the literature [10]. The arylidenemalononitriles 2a-n were synthesized by the Knoevenagel condensation of the corresponding arylaldehydes with malononitrile in aqueous MeOH (H 2 O-MeOH, 1:1) at room temperature in 90-95% yields.…”

Section: Methodsmentioning

confidence: 70%

“…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%

“…The starting materials, 4-aminocoumarin (1) and arylidenemalononitriles 2a-n were obtained by known methods [10,[16][17][18][19][20]. In our condensation protocol, no organic solvents or catalysts were used in the reaction process.…”

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confidence: 99%

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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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Section: Methodsmentioning

confidence: 70%

mentioning

confidence: 99%

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

Motamedi

2013

Chem Heterocycl Comp

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“…A G482 mutant ABCG2-overexpressing, drug-resistant colon cancer cell line, S1-M1-80, was maintained in medium with 80 µM mitoxantrone (Miri et al, 2011;Robey et al, 2001). The assay media for PXR transactivation assays included phenol red-free DMEM (Lonza) supplemented with 5% charcoal/dextran-treated FBS (HyClone) and the other additives.…”

Section: Cell Culturementioning

confidence: 99%

Synthesis and biological evaluation of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives as inhibitors of colon cancer cell growth

Guo

et al. 2015

Bangladesh J Pharmacol

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A convenient synthesis of 6H-1-benzopyrano [4,3-b]quinolin-6-one derivatives was reported using 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with different aromatic amines using silica sulfuric acid. The compounds were tested for their anticancer activity against colon (HCT-116 and S1-MI-80), prostate (PC3 and DU-145), breast (MCF-7 and MDAMB-231) cancer cells. These compounds showed more selectivity and potent cytotoxic activity against colon cancer cells. 3c was tested against five other colon cancer cell lines (HT-29, HCT-15, LS-180, LS-174, and LoVo), which had similar cytotoxicity and selectivity. 3c did not induce PXR-regulated ABCB1 or ABCG2 transporters. In fact, 3c induced cytotoxicity in HEK293 cells over expressing ABCB1 or ABCG2 to the same extent as in normal HEK293 cells. It was cytotoxic approximately 3-and 5-fold to resistant colon carcinoma S1-MI-80 cells. 3c also produced concentration-dependent changes in HCT-116 colon cancer cells, in mitochondrial membrane potential, leading to apoptosis, and submicromolar concentrations caused chromosomal DNA fragmentation. Article Info

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“…香豆素衍生物是一类广泛存在于自然界中的重要的杂环化合物, 具有明显的抗凝结、抗癌症及抗 HIV 等生物活性 [4] . 其中吡啶并香豆素类化合物由于具有抑制单胺氧化酶 [5] 、抗肿瘤 [6] 、止痛 [7] 、抗菌 [8] [9] (结构式 A), 二氢喹啉并[3,2-c]香豆素 [10] (结构式 B), 具有抗肿瘤活性的四氢喹啉并[3,2-c]香豆素 [11] (结构式 C)等, 成为香豆素类化合物研究领域中的一个热点. 最近, 我们以稠杂环化合物为研究对象, 先后合成了具有潜在生物活性的含吡啶 [12] 、吡喃 [13] 、呋喃 [14] 、香豆素 [15] [17] 受到关注, 但在碘作用下的该类反应报道不多 [18] .…”

Section: 4-二氢吡啶并[32-c]香豆素类衍生物的有效合成unclassified