Synthesis and cytotoxic evaluation of novel dihydrobenzo[h]cinnoline-5,6-diones

Thi, Tuyet Anh Dang; Decuyper, Lena; Phương, Hoàng Thị; Ngoc, Doan Vu; Nguyen, Ha Thanh; Nguyen, Tra Thanh; Huy, Thanh Do; Nguyen, Hung Huy; D’hooghe, Matthias; Nguyen, Tuyen Van

doi:10.1016/j.tetlet.2015.08.084

Cited by 14 publications

(4 citation statements)

References 49 publications

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“…Several lead 1,4-naphthoquinone compounds are lawsone, α-lapachone and bostrycoidin). The synthesis of bioactive 1,4-naphthoquinone derivatives based on multicomponent domino reactions is currently one of major research strategies of our group [3][4][5][6][7].…”

Section: _______mentioning

confidence: 99%

A Green and Efficient NH4OAc-catalyzed Synthesis of 2-Hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones

Giang

Anh²,

Thành³

et al. 2022

NST

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The green and efficient approach for synthesis of 2-hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones starting from 2-hydroxy-1,4-naphthoquinone, tetronic acid, and aromatic aldehydes was developed. These reactions were carried out in ethanol under microwave irradiation in the presence of ammonium acetate as catalyst. These multicomponent domino reactions presumably occur via NH4OAc-catalyzed Mannich reaction - Michael addition - hydration - tautomerism - elimination sequence of reactions.

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Section: _______mentioning

confidence: 99%

A Green and Efficient NH4OAc-catalyzed Synthesis of 2-Hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones

Giang

Anh²,

Thành³

et al. 2022

NST

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“…Nine of the new dihydrobenzo[ h ]cinnoline-5,6-diones displayed a considerable activity profile with IC 50 values below 5µM against both cell lines. A compound with a 4-NO 2 C 6 H 4 substituent was identified as the most promising agent with IC 50 values of 0.56 µM and 0.77 µM against the KB and Hep-G2 cell lines, respectively [83].…”

Section: Biological Activity Of Cinnoline Derivativesmentioning

confidence: 99%

Cinnoline Scaffold—A Molecular Heart of Medicinal Chemistry?

Szumilak

Stańczak

2019

Molecules

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The cinnoline nucleus is a very important bicyclic heterocycle that is used as the structural subunit of many compounds with interesting pharmaceutical properties. Cinnoline derivatives exhibit broad spectrum of pharmacological activities such as antibacterial, antifungal, antimalarial, anti-inflammatory, analgesic, anxiolytic and antitumor activities. Some of them are under evaluation in clinical trials. In the present review, we have compiled studies focused on the biological properties of cinnoline derivatives conducted by many research groups worldwide between 2005 and 2019. Comprehensive and target oriented information clearly indicate that the development of cinnoline based molecules constitute a significant contribution to the identification of lead compounds with optimized pharmacodynamic and pharmacokinetic properties.

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“…Also, their derivatives have exhibited remarkable properties in n-channel semiconductors 7 and cell imaging. 8 Accordingly, several protocols have been introduced for the synthesis of cinnolines from different starting materials, including arenediazonium salts, 9 arylsulfonylhydrazones, 10 methylhydrazine, 11 and nitriles. 12 However, introducing a new procedure for the synthesis of cinnoline derivatives using a greener and more sustainable catalyst is highly desirable, and in the present work, we report diphenhydramine hydrochloride–CuCl ([HDPH]Cl–CuCl) as a new catalyst for the synthesis of tetrahydrocinnolin-5(1 H )-ones.…”

Section: Introductionmentioning

confidence: 99%

Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)-ones

et al. 2023

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The current study deals with the synthesis and characterization of a novel catalyst made from diphenhydramine hydrochloride and CuCl ([HDPH]Cl−CuCl). The prepared catalyst was thoroughly characterized using various techniques, such as 1 H NMR, Fourier transform-infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis and derivative thermogravimetry. More importantly, the observed hydrogen bond between the components was proven experimentally. The activity of this catalyst was checked in the preparation of some new derivatives of tetrahydrocinnolin-5(1H)ones via a multicomponent reaction between dimedone, aromatic aldehydes, and aryl/alkyl hydrazines in ethanol as a green solvent. Also, for the first time, this new homogeneous catalytic system was effectively used for the preparation of unsymmetric tetrahydrocinnolin-5(1H)-one derivatives as well as mono-and bis-tetrahydrocinnolin-5(1H)-ones from two different aryl aldehydes and dialdehydes, respectively. The effectiveness of this catalyst was further confirmed by the preparation of compounds containing both tetrahydrocinnolin-5(1H)one and benzimidazole moieties from dialdehydes. The one-pot operation, mild conditions, rapid reaction, and high atom economy, along with the recyclability and reusability of the catalyst, are other notable features of this approach.

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Synthesis and cytotoxic evaluation of novel dihydrobenzo[h]cinnoline-5,6-diones

Cited by 14 publications

References 49 publications

A Green and Efficient NH4OAc-catalyzed Synthesis of 2-Hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones

A Green and Efficient NH4OAc-catalyzed Synthesis of 2-Hydroxy-3-(arylmethyl)(4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-1,4-naphthoquinones

Cinnoline Scaffold—A Molecular Heart of Medicinal Chemistry?

Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)-ones

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