52910-89-1

Upstream product

• 16063-05-1 2-(4-nitrophenyl)-4H-3,1-benzoxazin-4-one 
• 153172-75-9 N-(2-cyanophenyl)-4-nitrobenzamide 
• 122-04-3 4-nitro-benzoyl chloride 
• 28144-70-9 anthranilic acid amide 
• 5900-59-4 2-amino-4-chlorobenzamide 

Downstream Products

• 4765-59-7 2-(4-nitrophenyl)-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Structure-activity relationships of 2-arylquinazolin-4-ones as highly selective and potent inhibitors of the tankyrases

Tankyrases (TNKSs), members of the PARP (Poly(ADP-ribose)polymerases) superfamily of enzymes, have gained interest as therapeutic drug targets, especially as they are involved in the regulation of Wnt signalling. A series of 2-arylquinazolin-4-ones with varying substituents at the 8-position was synthesised. An 8-methyl group (compared to 8-H, 8-OMe, 8-OH), together with a 4′-hydrophobic or electron-withdrawing group, provided the most potency and selectivity towards TNKSs. Co-crystal structures of selected compounds with TNKS-2 revealed that the protein around the 8-position is more hydrophobic in TNKS-2 compared to PARP-1/2, rationalising the selectivity. The NAD+-binding site contains a hydrophobic cavity which accommodates the 2-aryl group; in TNKS-2, this has a tunnel to the exterior but the cavity is closed in PARP-1. 8-Methyl-2-(4-trifluoromethylphenyl)quinazolin-4-one was identified as a potent and selective inhibitor of TNKSs and Wnt signalling. This compound and analogues could serve as molecular probes to study proliferative signalling and for development of inhibitors of TNKSs as drugs.

Computer-aided design, synthesis and validation of 2-phenylquinazolinone fragments as CDK9 inhibitors with anti-HIV-1 tat-mediated transcription activity

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

One-pot synthesis of quinazolinone and benzamide derivatives using SBA-Pr-SO3H as a nanoporous heterogeneous acid catalyst

A series of quinazolinone and benzamide derivatives have been efficiently synthesized in good to excellent yields via the reaction of 2-aminobenzamide and aromatic benzoyl chlorides under solvent-free conditions using SBA-Pr-SO 3H as a nano solid acid catalyst.

Kinetics and mechanism of the base-catalysed cyclisation of 2-(substituted benzoylamino)benzamides giving quinazolin-4-one and quinazolin-4-thione derivatives

Acylation of 2-aminobenzamide and 2-(methylamino)benzamide with substituted benzoyl chlorides in acetone has been used to prepare the respective 2-(substituted benzoylamino)benzamides 1a-i, which were then subjected to sodium methoxide catalysed ring closure to give the respective 2-(substituted phenyl)quinazolin-4 -ones 2a-i. The kinetics of the cyclisation reactions were monitored by UV/Vis spectroscopy at 25 °C in methanolic solutions of sodium methoxide. In the case of 2-(substituted benzoylamino)benzamides 1a-i and 2-(substituted benzoylamino)thiobenzamides 3a-j, non-linear dependences of observed rate constants κobs on the sodium methoxide concentrations were obtained, the shape of them being typical of a reaction with rapid pre- equilibrium. All the cyclisation reactions satisfactorily obeyed the Hammett correlation. In the case of 2 - [(benzoyl) (methyl) amino] benzamides 1e-i, increasing sodium methoxide concentration resulted in a progressive increase in κobs values which is probably due to formation of dianion. In the case of 2-(substituted benzoylamino)thiobenzamides 3b and 3h, which differ in the presence of a methyl group on the nitrogen atom the values of the activation Gibbs energy ΔG? 25 °C, activation enthalpy ΔH? 25 °C, and activation entropy ΔS? 25 °C for their respective cyclisations to 2-(substituted phenyl)quinazoline-4-thiones 4b and 4h were determined. Whereas the ΔG? 25 °C values were very close for the two substances, the ΔH? 25 °C and ΔS? 25 °C distinctly differed. This was interpreted by the enthalpy and entropy factors operating against each other in the cyclisation. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Mechanism of alkaline cyclization of 2-(substituted benzamido)benzamides to 4-quinazolinones

The title amides cyclize rapidly to the corresponding quinazolin-4-ones in aqueous alkaline solution at 25°C; the pseudo-first-order rate constants fit the empirical equation k(obs) = k(max) [OH-]/(K(m) + [OH-] + [OH-]sup