Recent advances in the synthesis of Quinazoline analogues as Anti-TB agents

Dutta, Apurba; Sarma, Diganta

doi:10.1016/j.tube.2020.101986

Cited by 37 publications

(12 citation statements)

References 51 publications

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“…From medicinal chemists’ viewpoint, 2,3-dihydroquinazolin-4(1 H )-ones have received immense attention in the last few decades as they possess a wide range of biological activities. − Therefore, efforts have been devoted in developing effective, new, and useful synthetic protocols for 2,3-dihydroquinazolin-4(1 H )-ones. Among the therapeutic activities, large numbers of quinazolines also show anti-tubercular (anti-TB) activity with moderate to excellent potency − (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Quinazolinone-Triazole Hybrids as Potent Anti-Tubercular Agents

Dutta

Trivedi

Gehlot

et al. 2022

ACS Appl. Bio Mater.

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A straightforward and convenient methodology has been developed for the reaction of 2-aminobenzamide and carbonyls affording 2,3-dihydroquinazolin-4(1H)-ones using aqueous solution of [C 12 Py][FeCl 3 Br]. The developed methodology was applied for the synthesis of 25 quinazolinone-triazole hybrids followed by evaluation of their in vitro anti-tubercular (TB) activity. The results revealed that 8 quinazolinone-triazole hybrids displayed promising activity having MIC values of 0.78−12.5 μg/ mL. The compound 3if with MIC 0.78 μg/mL was found to be the lead nominee among the series, better than Ethambutol, a first line anti-TB drug and comparable with Rifampicin. The active compounds with MIC values ≤ 6.25 μg/mL were subjected to in vitro cytotoxicity and found nontoxic. In drug−drug interaction, compounds 3ia and 3ii interacted synergistically with all the three anti-TB drugs, INH, RFM, and EMB. Other 3 compounds interacted either in synergistic or additive manners. Important information on the binding interaction of the target compounds with the active sites of 1DQY Antigen 85C from Mycobacterium tuberculosis and Enoyl acyl carrier protein reductase (InhA) enzymes was obtained from molecular docking studies. Screening of the drug-likeness properties and bioactivity score indicates that synthesized molecules could be projected as potential drug candidates. Based on the current study, quinazolinone-triazole hybrids framework can be useful in drug development for TB.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Quinazolinone-Triazole Hybrids as Potent Anti-Tubercular Agents

Dutta

Trivedi

Gehlot

et al. 2022

ACS Appl. Bio Mater.

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“…Therefore, there is an urgent need to find novel and selective compounds as antiproliferative agents. Quinazoline scaffolds have been shown to have various biological and pharmacological effects including anti-cancer [6][7][8], anti-diabetes [9], antifungal [10], antibacterial [11,12], antihypertensive [13] and anti-tuberculosis activity [14]. In addition, there are various quinazoline scaffold based compounds in the market such as erlotinib, gefitinib (structures I and II) and structures III-VI, with high cytotoxic activity toward different cancerous cell lines (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation, and computational studies of some novel quinazoline derivatives as anticancer agents

et al. 2022

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A series of quinazolinone derivatives (7a–7h) were synthesized as antiproliferative agents. All compounds, were synthesized through three steps method and structurally evaluated by FTIR, 1H-NMR, 13CNMR and Mass spectroscopy. Their cytotoxic activities were assessed using MTT protocol against three humans cancerous (MCF-7, A549 and 5637) and normal (MRC-5) cell lines. In addition, molecular docking and simulation studies of the synthesized compounds were performed to assessment their orientation, interaction mode against EGFR as plausible mechanism of quinazoline compounds as anticancer agents. The synthesized compounds mostly showed moderate activity against the three studied cell lines. They also indicated an appropriate selectivity against tumorigenic and non-tumorigenic cell line. The molecular docking results also confirmed biological activity. Most of the compounds fulfilled Lipinski rule. Collectively, these compounds with further modification can be considered as potent antiproliferative agents.

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“…Quinazoline as nitrogen-containing heterocyclic compound is synthesized in the structure of many synthetic compounds using different synthetic methods including aza-diels–alder reaction, aza-wittig reaction, metal-mediated reaction, and oxidative cyclization [ 8 – 12 ]. Quinazoline scaffold show diverse biologically and pharmacologically active anti-cancer [ 13 ], analgesic [ 14 ], anti-tuberculosis [ 15 ], antihypertensive [ 16 ], anti-diabetes [ 17 ] anti-melanogenesis [ 18 , 19 ], anti-urease [ 20 ], antifungal [ 21 ], and antibacterial [ 22 , 23 ] agents. Quinazolinone is a naturally occurring alkaloid that can be found in many natural products with diverse biological activities [ 24 – 26 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents

et al. 2022

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Background Cancer is the most cause of morbidity and mortality, and a major public health problem worldwide. In this context, two series of quinazolinone 5a–e and dihydroquinazolinone 10a–f compounds were designed, synthesized as cytotoxic agents. Methodology All derivatives (5a–e and 10a–f) were synthesized via straightforward pathways and elucidated by FTIR, 1H-NMR, CHNS elemental analysis, as well as the melting point. All the compounds were evaluated for their in vitro cytotoxicity effects using the MTT assay against two human cancer cell lines (MCF-7 and HCT-116) using doxorubicin as the standard drug. The test derivatives were additionally docked into the PARP10 active site using Gold software. Results and discussion Most of the synthesized compounds, especially 5a and 10f were found to be highly potent against both cell lines. Synthesized compounds demonstrated IC50 in the range of 4.87–205.9 μM against HCT-116 cell line and 14.70–98.45 μM against MCF-7 cell line compared with doxorubicin with IC50 values of 1.20 and 1.08 μM after 72 h, respectively, indicated the plausible activities of the synthesized compounds. Conclusion The compounds quinazolinone 5a–e and dihydroquinazolinone 10a–f showed potential activity against cancer cell lines which can lead to rational drug designing of the cytotoxic agents.

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Recent advances in the synthesis of Quinazoline analogues as Anti-TB agents

Cited by 37 publications

References 51 publications

Design and Synthesis of Quinazolinone-Triazole Hybrids as Potent Anti-Tubercular Agents

Design and Synthesis of Quinazolinone-Triazole Hybrids as Potent Anti-Tubercular Agents

Synthesis, biological evaluation, and computational studies of some novel quinazoline derivatives as anticancer agents

Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents

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