A Review on 2-Heteryl- and Heteroalkyl 4(3H)-quinazolinones

Reddy, P. S. N.; Reddy, Padi Pratap; Vasantha, T.

doi:10.3987/rev-01-540

Cited by 58 publications

(1 citation statement)

References 15 publications

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“…Synthesis of nitrogen and oxygen containing functionalized heterocyclic compounds is highly desirable owing to the enormous pharmacological and biological properties . Quinazolinones, a benzene ring-fused pyrimidinones, are important scaffolds found in various biologically active natural and veterinary products, agrochemicals, synthetic compounds, and pharmaceutical drugs . The biological properties of quinazolinones include anticancer, anti-inflammatory, antimalarial, dihydrofolate reductase inhibition, anticholinesterase, anticonvulsant, antihypertensive, antidiabetic, diuretic, antipsychotic, dopamine agonist, and antimicrobial activities .…”

Section: Introductionmentioning

confidence: 99%

Diversity-Oriented Synthesis of Benzo[f][1,4]oxazepine-, 2H-Chromene-, and 1,2-Dihydroquinoline-Fused Polycyclic Nitrogen Heterocycles under Microwave-Assisted Conditions

et al. 2023

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An efficient, diversity-oriented synthesis of oxazepino[5,4-b]quinazolin-9-ones, 6H-chromeno[4,3-b]quinolines, and dibenzo[b,h][1,6]naphthyridines was established involving a substrate-based approach under microwave-assisted and conventional heating conditions in high yields (up to 88%). The CuBr2-catalyzed, chemoselective cascade annulation of O-propargylated 2-hydroxybenzaldehydes and 2-aminobenzamides delivered oxazepino[5,4-b]quinazolin-9-ones involving a 6-exo-trig cyclization-air oxidation-1,3-proton shift-7-exo-dig cyclization sequence. This one-pot process showed excellent atom economy (−H2O) and constructed two new heterocyclic rings (six- and seven-membered) and three new C–N bonds in a single synthetic operation. On the other side of diversification, the reaction between O/N-propargylated 2-hydroxy/aminobenzaldehydes and 2-aminobenzyl alcohols delivered 6H-chromeno[4,3-b]quinolines and dibenzo[b,h][1,6]naphthyridines involving sequential imine formation-[4 + 2] hetero-Diels–Alder reaction-aromatization steps. The influence of microwave assistance was superior to conventional heating, where the reactions were clean, rapid, and completed in 15 min, and the conventional heating required a longer reaction time at a relatively elevated temperature.

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Section: Introductionmentioning

confidence: 99%

Diversity-Oriented Synthesis of Benzo[f][1,4]oxazepine-, 2H-Chromene-, and 1,2-Dihydroquinoline-Fused Polycyclic Nitrogen Heterocycles under Microwave-Assisted Conditions

et al. 2023

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A Review on 2‐Heteryl and Heteroalkyl‐4(3H)‐quinazolinones

Reddy

Vasantha

2003

ChemInform

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Computer‐Aided Design, Synthesis and Validation of 2‐Phenylquinazolinone Fragments as CDK9 Inhibitors with Anti‐HIV‐1 Tat‐Mediated Transcription Activity

et al. 2013

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The activity of the cyclin‐dependent kinase 9 (CDK9) is critical for HIV‐1 Tat‐mediated transcription and represents a promising target for antiviral therapy. Here we present computational studies that, along with preliminary synthetic efforts, allowed us to identify and characterize a new class of nontoxic anti‐CDK9 chemotypes based on the 2‐phenylquinazolinone scaffold. Inhibition of CDK9 translated into the ability to interfere selectively with Tat‐mediated transactivation of the viral promoter and in the inhibition of HIV‐1 reactivation from latently infected cells, with the most potent derivative 37 (2‐(4‐aminophenyl)‐7‐chloroquinazolin‐4(3H)‐one) showing an IC50 value of 4.0 μM. Because the herein reported 2‐phenylquinazolinones are merely fragments, they are largely optimizable, paving the way to derivatives with improved potency.

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A Review on 2-Heteryl- and Heteroalkyl 4(3H)-quinazolinones

Cited by 58 publications

References 15 publications

Diversity-Oriented Synthesis of Benzo[f][1,4]oxazepine-, 2H-Chromene-, and 1,2-Dihydroquinoline-Fused Polycyclic Nitrogen Heterocycles under Microwave-Assisted Conditions

Diversity-Oriented Synthesis of Benzo[f][1,4]oxazepine-, 2H-Chromene-, and 1,2-Dihydroquinoline-Fused Polycyclic Nitrogen Heterocycles under Microwave-Assisted Conditions

A Review on 2‐Heteryl and Heteroalkyl‐4(3H)‐quinazolinones

Computer‐Aided Design, Synthesis and Validation of 2‐Phenylquinazolinone Fragments as CDK9 Inhibitors with Anti‐HIV‐1 Tat‐Mediated Transcription Activity

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