GRINDING SYNTHESIS OF 2-AMINO-4H-CHROMENES USING 3,3-(BUTANE-1,4-DIYL) BIS (1,2-DIMETHYL- 1H-IMIDAZOLE-3-IUM)Br-CAN AS A NOVEL REAGENT

Nikpassand, Mohammad; Fekri, Leila Zare; Ahmadi, Parvin

doi:10.4067/s0717-97072017000100019

Cited by 9 publications

(1 citation statement)

References 20 publications

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“…Among the different approaches for synthesizing 4H-chromenes are multicomponent reactions [27,28] assisted by microwave irradiation [29], sonication [30], electrocatalysis [31], mechanochemistry [32], and infrared radiation (IR) [33]. They can also be obtained by cyclocondensation reactions [34] with heterogeneous phase catalysts [35], through the oxidation of 2H-chromenes and dihydro-1-benzoxepines with hypervalent iodine [36].…”

Section: Introductionmentioning

confidence: 99%

Three-Component Synthesis of 2-Amino-3-cyano-4H-chromenes, In Silico Analysis of Their Pharmacological Profile, and In Vitro Anticancer and Antifungal Testing

et al. 2021

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Chromenes are compounds that may be useful for inhibiting topoisomerase and cytochrome, enzymes involved in the growth of cancer and fungal cells, respectively. The aim of this study was to synthesize a series of some novel 2-amino-3-cyano-4-aryl-6,7-methylendioxy-4H-chromenes 4a–o and 2-amino-3-cyano-5,7-dimethoxy-4-aryl-4H-chromenes 6a–h by a three-component reaction, and test these derivatives for anticancer and antifungal activity. Compounds 4a and 4b were more active than cisplatin (9) and topotecan (7) in SK-LU-1 cells, and more active than 9 in PC-3 cells. An evaluation was also made of the series of compounds 4 and 6 as potential antifungal agents against six Candida strains, finding their MIC50 to be less than or equal to that of fluconazole (8). Molecular docking studies are herein reported, for the interaction of 4 and 6 with topoisomerase IB and the active site of CYP51 of Candida spp. Compounds 4a–o and 6a–h interacted in a similar way as 7 with key amino acids of the active site of topoisomerase IB and showed better binding energy than 8 at the active site of CYP51. Hence, 4a–o and 6a–h are good candidates for further research, having demonstrated their dual inhibition of enzymes that participate in the growth of cancer and fungal cells.

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Section: Introductionmentioning

confidence: 99%

Three-Component Synthesis of 2-Amino-3-cyano-4H-chromenes, In Silico Analysis of Their Pharmacological Profile, and In Vitro Anticancer and Antifungal Testing

et al. 2021

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Ionic liquid‐assisted synthesis of 2‐amino‐3‐cyano‐4H‐chromenes: A sustainable overview

Chatterjee¹,

Bhukta²,

Dandela³

2021

Journal of Heterocyclic Chem

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In advanced research, the role of ionic liquid is gradually enhanced as an alternative finding. For a long time, many strategies have been developed based on the ionic liquid conveying the role of greener solvents or catalysts. In the case of multi‐component synthesis, ionic liquids have a wide range of applications to revise a method in a sustainable and greener approach. The last two decades have given a number of methods to achieve the 4H‐chromene derivatives by applying different types of ionic liquids. Especially, 2‐amino‐3‐cyano‐4H‐chromene moiety that exhibits pharmacological and biological activity, have been synthesized using simple or functionalized ionic liquids such as basic, acidic, neural, metal‐tagged, or carbon‐oriented ionic liquid. In this review, we have concised the multicomponent reactions that have been reported to synthesize the 4H‐chromene derivatives following the versatility of ionic liquids.

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Green Synthesis of Some 2‐Amino‐4 h‐Benzo[H]Chromene Derivatives in the Presence of Bimetallic Nanocomposite Based on Magnetic Mesoporous Silica Nanoparticles at Ambient Conditions

Ahmadi,

Moradi

2024

ChemistrySelect

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In this research, some of 2‐amino‐4H‐benzo[h]chromene derivatives were synthesized by multicomponent reaction of 1‐naphthol, benzaldehyde derivatives and malononitrile. The reaction was performed under green conditions using water as the solvent in the presence of heterogeneous nano catalyst containing Co(II) and Cu(II) stabilized on magnetic mesoporous silica nanoparticles/tannic acid (M–MSN/TA/Co(II),Cu(II)) at room temperature. The prepared catalyst showed excellent efficiency and its magnetic properties allow easy separation. The structure and morphology of prepared catalyst was identified using Fourier transform infrared (FT‐IR), X‐ray diffraction (XRD), field emission scanning electron microscopy (FE‐SEM), energy dispersive X‐ray spectroscopy (EDX), elemental mapping, thermogravimetric analysis (TGA) and vibrating‐sample magnetometry (VSM) analysis. All of products were obtained in high to excellent yields (78–94 %) after short reaction times (20–45 min) in optimal conditions and their structures were confirmed using FT‐IR and Proton nuclear magnetic resonance (1H NMR) spectroscopic techniques. This study shows that the M–MSN/TA/Cu(II), Co(II) presents a good catalytic activity, reusability and stability compared to other catalysts.

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GRINDING SYNTHESIS OF 2-AMINO-4H-CHROMENES USING 3,3-(BUTANE-1,4-DIYL) BIS (1,2-DIMETHYL- 1H-IMIDAZOLE-3-IUM)Br-CAN AS A NOVEL REAGENT

Cited by 9 publications

References 20 publications

Three-Component Synthesis of 2-Amino-3-cyano-4H-chromenes, In Silico Analysis of Their Pharmacological Profile, and In Vitro Anticancer and Antifungal Testing

Three-Component Synthesis of 2-Amino-3-cyano-4H-chromenes, In Silico Analysis of Their Pharmacological Profile, and In Vitro Anticancer and Antifungal Testing

Ionic liquid‐assisted synthesis of 2‐amino‐3‐cyano‐4H‐chromenes: A sustainable overview

Green Synthesis of Some 2‐Amino‐4 h‐Benzo[H]Chromene Derivatives in the Presence of Bimetallic Nanocomposite Based on Magnetic Mesoporous Silica Nanoparticles at Ambient Conditions

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