Anti-TB evaluation of novel 2,3-dihydroquinazolin-4(1H)-ones and in silico studies of the active compounds

Dutta, Apurba; Trivedi, Priyanka; Gogoi, Dipshikha; Chetia, Pankaj; Chaturvedi, Vinita; Sarma, Diganta

doi:10.1007/s00044-021-02733-6

Cited by 5 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.

Self Cite

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“…2,3-Dihydroquinazolin-4(1H)-ones are privileged structural motifs that exhibit a wide range of pharmacological activities including antitubercular, [1] antibacterial, [2] antidiabetic, [3] anticancer, [4] anti-toxin, [5] and anti-inflammatory. [6] Several marketed drugs such metolazone [7] as antihypertensive and diuretic, Afloqualone [8] which is used as centrally acting muscle relaxant, and albaconazole [9] as antifungal agent feature 2,3-dihydroquinazolinone and quinazolinone skeleton respectively (Figure 1).…”

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confidence: 99%