Renaissance of 4-(5-nitrofuran-2-yl)-5-arylamino substituted pyrimidines: microwave-assisted synthesis and antitubercular activity

Verbitskiy, Egor V.; Baskakova, Svetlana A.; Belyaev, Danila V.; Vakhrusheva, Diana; Eremeeva, Natalya; Rusinov, Gennady L.; Charushin, Valery N.

doi:10.1016/j.mencom.2021.03.021

Cited by 11 publications

(5 citation statements)

References 17 publications

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“…The study of the antimycobacterial activity of the compounds was carried out based on the previously described procedure. [11,15] For details see Supporting Information.…”

Section: Discussionmentioning

confidence: 99%

New Approach to Biologically Active Indolo[2,3‐b]quinoxaline Derivatives through Intramolecular Oxidative Cyclodehydrogenation

Verbitskiy

2022

ChemistrySelect

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A convenient synthetic protocol to antiviral agent B‐220 and a series of similar indolo[2,3‐b]quinoxaline derivatives has been developed. This synthetic approach is based on Buchwald‐Hartwig cross‐coupling and subsequent annulation by intramolecular oxidative cyclodehydrogenation. For the first time, 6H‐indolo[2,3‐b]quinoxaline amine derivatives were evaluated for antimycobacterial activity. The moderate bacteriostatic effect against Mycobacterium tuberculosis H37Rv was found. A plausible mechanism of antibacterial action was elucidated by the molecular docking.

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“…The study of the antimycobacterial activity of the compounds was carried out based on the previously described procedure. [11,15] For details see Supporting Information.…”

Section: Discussionmentioning

confidence: 99%

New Approach to Biologically Active Indolo[2,3‐b]quinoxaline Derivatives through Intramolecular Oxidative Cyclodehydrogenation

Verbitskiy

2022

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“…Additionally, we found that triazinylamino-and triazinyloxy-diazepines 28a-g, 29a,c,d,f, 30d, 31a-f, 32a,b,f,g, 33a,b,c,f showed inhibition against N. gonorrhoeae with MIC values between 0.25 and 62.5 µg/mL (Table 3). This could suggest that the pyrimido[4,5-b] [1,4]diazepine moiety may be associated to the activity against N. gonorrhoeae [80]. Moreover, diazepines containing the p-aryloxy linker 28a-g and N-(2-aminoethyl)benzenesulfonamide linker 31a-f showed inhibition with MIC values between 0.25-500 µg/mL and 0.5-8 µg/mL, being, the triazinylamino-diazepine 31f the compound with the highest activity against N. gonorrhoeae with a MIC value 0.25 µg/mL, which is similar to that for penicillin [81].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents

Moreno,

Quiroga,

Abonia

et al. 2024

IJMS

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This study presents the synthesis of four series of novel hybrid chalcones (20,21)a–g and (23,24)a–g and six series of 1,3,5-triazine-based pyrimido[4,5-b][1,4]diazepines (28–33)a–g and the evaluation of their anticancer, antibacterial, antifungal, and cytotoxic properties. Chalcones 20b,d, 21a,b,d, 23a,d–g, 24a–g and the pyrimido[4,5-b][1,4]diazepines 29e,g, 30g, 31a,b,e–g, 33a,b,e–g exhibited outstanding anticancer activity against a panel of 60 cancer cell lines with GI50 values between 0.01 and 100 μM and LC50 values in the range of 4.09 μM to >100 μM, several of such derivatives showing higher activity than the standard drug 5-fluorouracil (5-FU). On the other hand, among the synthesized compounds, the best antibacterial properties against N. gonorrhoeae, S. aureus (ATCC 43300), and M. tuberculosis were exhibited by the pyrimido[4,5-b][1,4]diazepines (MICs: 0.25–62.5 µg/mL). The antifungal activity studies showed that triazinylamino-chalcone 29e and triazinyloxy-chalcone 31g were the most active compounds against T. rubrum and T. mentagrophytes and A. fumigatus, respectively (MICs = 62.5 μg/mL). Hemolytic activity studies and in silico toxicity analysis demonstrated that most of the compounds are safe.

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“…Nitrofuranes have been known as antibacterials for decades. In recent years a limited number of nitrofuranyl compounds were tested in vitro and in vivo as potential anti-tubercular agents recent [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Acute and Sub-Acute Toxicity, Oxidative Stress and Molecular Docking of Two Nitrofuranyl Amides as Promising Anti-Tuberculosis Agents

Dimitrov,

Slavchev,

Simeonova

et al. 2023

Biomolecules

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Tuberculosis (TB) remains a widespread infectious disease and one of the top 10 causes of death worldwide. Nevertheless, despite significant advances in the development of new drugs against tuberculosis, many therapies and preventive measures do not lead to the expected favorable health results for various reasons. The aim of this study was to evaluate the acute and sub-acute toxicity and oxidative stress of two selected nitrofuranyl amides with high in vitro antimycobacterial activity. In addition, molecular docking studies were performed on both compounds to elucidate the possibilities for further development of new anti-tuberculosis candidates with improved efficacy, selectivity, and pharmacological parameters. Acute toxicity tests showed that no changes were observed in the skin, coat, eyes, mucous membranes, secretions, and vegetative activity in mice. The histological findings include features consistent with normal histological architecture without being associated with concomitant pathological conditions. The observed oxidative stress markers indicated that the studied compounds disturbed the oxidative balance in the mouse liver. Based on the molecular docking, compound DO-190 showed preferable binding energies compared to DO-209 in three out of four targets, while both compounds showed promising protein–ligand interactions. Thus, both studied compounds displayed promising activity with low toxicity and can be considered for further evaluation and/or lead optimization.

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Renaissance of 4-(5-nitrofuran-2-yl)-5-arylamino substituted pyrimidines: microwave-assisted synthesis and antitubercular activity

Cited by 11 publications

References 17 publications

New Approach to Biologically Active Indolo[2,3‐b]quinoxaline Derivatives through Intramolecular Oxidative Cyclodehydrogenation

New Approach to Biologically Active Indolo[2,3‐b]quinoxaline Derivatives through Intramolecular Oxidative Cyclodehydrogenation

Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents

Evaluation of Acute and Sub-Acute Toxicity, Oxidative Stress and Molecular Docking of Two Nitrofuranyl Amides as Promising Anti-Tuberculosis Agents

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