Effect of <i>ortho</i>-substitution on persulfate-mediated decarboxylation and functionalization of arylacetic acids

Laha, Joydev K.; Gulati, Upma; Malik, Suman

doi:10.1039/d3nj02776g

Cited by 1 publication

(1 citation statement)

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“…To date, many methods have been developed for the synthesis of quinazolinones and their analogues due to their high applied significance [27]. The most common synthetic approach to quinazolin-4(3H)-ones involves the condensation of anthranilamides with aromatic aldehydes [28][29][30][31][32], ketones [33,34], alkynes [35], carboxylic acid [36], and their derivatives [37], benzyl alcohols [38], CO/aryl bromides [39], and methylarenes [40], etc. While approaches to quinazolin-4(3H)-ones are well known and capable of providing the formation of the desired framework, they suffer from certain drawbacks.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

Mendogralo,

Nesterova,

Nasibullina

et al. 2023

Molecules

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The treatment of many bacterial diseases remains a significant problem due to the increasing antibiotic resistance of their infectious agents. Among others, this is related to Staphylococcus aureus, especially methicillin-resistant S. aureus (MRSA) and Mycobacterium tuberculosis. In the present article, we report on antibacterial compounds with activity against both S. aureus and MRSA. A straightforward approach to 2-(1H-indol-3-yl)quinazolin-4(3H)-one and their analogues was developed. Their structural and functional relationships were also considered. The antimicrobial activity of the synthesized compounds against Mycobacterium tuberculosis H37Rv, S. aureus ATCC 25923, MRSA ATCC 43300, Candida albicans ATCC 10231, and their role in the inhibition of the biofilm formation of S. aureus were reported. 2-(5-Iodo-1H-indol-3-yl)quinazolin-4(3H)-one (3k) showed a low minimum inhibitory concentration (MIC) of 0.98 μg/mL against MRSA. The synthesized compounds were assessed via molecular docking for their ability to bind long RSH (RelA/SpoT homolog) proteins using mycobacterial and streptococcal (p)ppGpp synthetase structures as models. The cytotoxic activity of some synthesized compounds was studied. Compounds 3c, f, g, k, r, and 3z displayed significant antiproliferative activities against all the cancer cell lines tested. Indolylquinazolinones 3b, 3e, and 3g showed a preferential suppression of the growth of rapidly dividing A549 cells compared to slower growing fibroblasts of non-tumor etiology.

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Section: Introductionmentioning

confidence: 99%

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

Mendogralo,

Nesterova,

Nasibullina

et al. 2023

Molecules

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Effect of ortho-substitution on persulfate-mediated decarboxylation and functionalization of arylacetic acids

Abstract: Persulfate mediated decarboxylation of arylacetic acids is well-versed and a preferred choice for functionalization. However, certain substituted arylacetic acids do not follow the expected decarboxylation trend and may lead to...

Cited by 1 publication

References 65 publications

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

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