Synthesis, characterization, molecular docking and anticancer studies of fluoroaniline derivatives of hydroxybenzoquinone and hydroxynaphthoquinone

Arunkumar, B.; Fernandez, Annette; Laila, Shiny P.; Nair, Achuthsankar S.; Vishnu, V S

doi:10.1080/07391102.2020.1852116

Cited by 5 publications

References 27 publications

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Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer

Yilmaz Goler,

Tarbin Jannuzzi,

Biswas

et al. 2023

Chemistry & Biodiversity

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In an effort to develop potent and secure antiproliferative lead compounds, five quinolinequinones (AQQ1‐5) described previously have been selected and submitted to the National Cancer Institute (NCI) of Bethesda. Four of five quinolinequinones (AQQ2‐5) were selected for five‐dose screening and they displayed promising antiproliferative effects against several cancer types. All AQQs showed a super anticancer profile with low micromolar GI50 and TGI values against most cell lines. AQQ2‐5 reduced the proliferation of all some cell lines at a single dose and five additional doses. We investigated the in vitro cytotoxic activities of the most promising compounds, AQQ2 and AQQ3. Concomitantly, IC50 values of AQQ2 against MCF7 and T‐47D cell lines of breast cancer, DU‐145 cell line of prostate cancer, HCT‐116 cell line of colon cancer, and HaCaT human keratinocytes were determined. AQQ2 exhibited anticancer activity through the induction of apoptosis and caused alterations in the cell cycle. In silico pharmacokinetic studies of all analogs have been carried out against ATR, CHK1, WEE1, CDK1, and CDK2. In addition to this, in vitro ADME and in vivo pharmacokinetic profiling for the most effective AAQ (AAQ2).

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Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer

Yilmaz Goler,

Tarbin Jannuzzi,

Biswas

et al. 2023

Chemistry & Biodiversity

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Compounds Derived from 5‐Fluoropyridine and Benzo[b]thiophene: Killing Mycobacterium tuberculosis and Reducing its Virulence

Dong,

Chen,

Cai

et al. 2024

Chemistry & Biodiversity

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The rise of drug‐resistant Mycobacterium tuberculosis (Mtb) has extended the duration of tuberculosis (TB) treatment and reduced the likelihood of cure. One strategy to combat this issue is the development of inhibitors targeting the virulence factors of bacterial pathogens. Mtb' catalase (KatG) is crucial for its detoxification mechanisms and also serves as a significant virulence factor for the bacterium. In this study, twelve derivatives synthesized from 5‐fluoropyridine and benzo[b]thiophene demonstrated antimycobacterial efficacy with minimum inhibitory concentrations (MICs) varying between 0.5 and 32 µg/mL. Compound 2, 2‐(benzo[b]thiophene‐2‐ylmethylene) hydrazine‐1‐carbothioamide, emerged as the most potent candidate. It effectively inhibited Mtb KatG. Molecular docking revealed that compound 2 binds to the active site of Mtb‐KatG with docking score of 114. The rabbit skin tuberculosis model was employed to assess the virulence of Mtb. Animal study results indicated that the granulomas induced by Mtb after treatment with compound 2 were reduced in size, exhibited a lower bacterial load, and the bacteria were no longer aggregated, in contrast to those caused by untreated Mtb. Hence, compound 2 can be regarded as a molecule capable of neutralizing the virulence factors of Mtb. This research offers insights into the design of anti‐Mtb molecules with novel mechanisms of action.

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Synthesis of oxadiazole-thiadiazole fluorochromane hybrids and their antioxidant activity

Rupapara,

Chauhan,

Sangani

et al. 2023

Journal of Fluorine Chemistry

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Synthesis, characterization, molecular docking and anticancer studies of fluoroaniline derivatives of hydroxybenzoquinone and hydroxynaphthoquinone

Cited by 5 publications

References 27 publications

Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer

Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer

Compounds Derived from 5‐Fluoropyridine and Benzo[b]thiophene: Killing Mycobacterium tuberculosis and Reducing its Virulence

Synthesis of oxadiazole-thiadiazole fluorochromane hybrids and their antioxidant activity

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