Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives

Delmas, F.; Avellaneda, Antonio; Giorgio, Carole Di; Robin, Maxime; Clercq, Erik De; Timon‐David, P.; Galy, Jean‐Pierre

doi:10.1016/j.ejmech.2004.04.006

Cited by 119 publications

(54 citation statements)

References 20 publications

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“…Benzothiazoles are a class of bicyclic compounds with a broad spectrum of biological applications such as neuroprotective effects [1,2], antimicrobial activity [3][4][5][6], antioxidant and radioprotective effects [7], anticonvulsant activity [8,9] and antitumor properties [10,11]. In particular, 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole has been reported to be a tyrosinase inhibitor against hyperpigmentation [12].…”

Section: Introductionmentioning

confidence: 99%

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

et al. 2017

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Abstract:Benzothiazoles are a set of molecules with a broad spectrum of biological applications. In particular, 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole is a potential breast cancer cell suppressor whose mechanism of action has been previously reported. In the present work, the title compound was synthesized, crystallized, and its biological activity on HeLa cells was evaluated. Its molecular structure was compared to that obtained by molecular modeling. Theoretical calculations suggest that the syn-rotamer is the most stable form and correlates very well with crystallographic data. The crystal structure adopts a helical arrangement formed through O13-H13···N3 intermolecular hydrogen bonding that propagates in the (14 -1 -3) plane. These results suggest that the title compound has the capacity to interleave into DNA and better explain its biological effects related to the increased CHIP expression through AhR recruitment. Finally, the biological experiments indicate that the title compound has the capacity to decrease the viability of HeLa cells with an IC 50 = 2.86 µM.

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Section: Introductionmentioning

confidence: 99%

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

et al. 2017

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“…There are numerous functions of the acridone nucleus in addition to its derivatives that have been reported in previous studies, including anticancer (13-16), anti-herpes (17), anti-malarial (18,19), antivirus (20), anti-allergy (21) and anti-leishmanial (22) activities. These features are attributed to the semi planar heterocyclic structure, which interacts with different biomolecular targets.…”

Section: Discussionmentioning

confidence: 99%

Acridone suppresses the proliferation of human breast cancer cells inï¿½vitro via ATP-binding cassette subfamily G member 2

Liu

et al. 2017

Oncol Lett

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Abstract. In the past decades, the tricyclic acridone ring system has become a focus of major research by medicinal chemists due to the biological significance of this moiety in drug design and discovery. Acridone has substantial bio-potential since it performs crucial functions, including antibacterial, antimalarial, antiviral and anti-neoplastic activities. However, the anticancer effect and the underlying mechanisms of acridone on breast cancer cells remains unclear. In the present study, the anti-tumor function and the underlying mechanisms of acridone were evaluated in vitro. Firstly, an MTT assay was used to evaluate the inhibitory effect of acridone. Subsequently, reverse transcription-quantitative polymerase chain reaction (RT-qPCR) was performed to investigate whether ATP binding cassette subfamily G member 2 (ABCG2) was associated with the function of acridone. Finally, western blotting was used to confirm the results of RT-qPCR. The present study demonstrated that acridone may decrease the proliferation of MDA-MB-231 cells dose-dependently. Further experiments revealed that acridone may downregulate the mRNA and protein expression levels of ABCG2, supporting the potential application of acridone in breast cancer treatment. These findings suggested that acridone is a potential agent in the treatment of human breast cancer.

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“…Several methods have been reported [4][5][6] for the synthesis of quinoline derivatives which suffer from various problems like, usage of hazardous chemicals, application of poisonous and expensive solvents, less common catalysts, drastic reaction conditions, longer reaction time period, multistep synthesis and difficult work-up. These synthetic drawbacks have been overcome by developing this eco-friendly method 7,8 . The synthesis of quinoline derivatives has gained the interest for their therapeutic chemistry 9,10 .…”

Section: Introductionmentioning

confidence: 99%

An Eco-friendly Route to Synthesis of Quinolines

Mishra¹

2012

J. Nepal Chem. Soc.

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Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives

Cited by 119 publications

References 20 publications

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

Acridone suppresses the proliferation of human breast cancer cells inï¿½vitro via ATP-binding cassette subfamily G member 2

An Eco-friendly Route to Synthesis of Quinolines

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