1913-19-5

Upstream product

• 140215-74-3 2-formamidobenzamide 
• 104-94-9 4-methoxy-aniline 
• 1361234-34-5 methyl N-cyano-2-nitrobenzenecarboximidoate 
• 118-92-3 anthranilic acid 
• 86-96-4 1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 13519-16-9 N-(4-methoxyphenyl)cyanamide 
• 134-20-3 2-carbomethoxyaniline 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 119072-55-8 tert-butylisonitrile 
• 892455-34-4 1-(2-iodophenyl)-3-(4-methoxyphenyl)urea 
• 615-43-0 2-iodophenylamine 
• 1478441-16-5 N-{imino[(4-methoxyphenyl)amino]methyl}-2-nitrobenzamide 
• 607-68-1 2,4-dichloroquinazoline 
• 607-69-2 2-chloro-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Synthesis and enzymological characterization of some 2-(Substituted-phenylamino)quinazolin-4(3h)-one derivatives as potent α-glucosidase inhibitors in vitro

Background: α-Glucosidase is an important hydrolytic enzyme playing a vital role in digestion of carbohydrates. It catalyzes the final step of carbohydrates digestion in biological systems and converts unabsorbed oligosaccharides and disaccharides into monosaccharides, thus resulting in hyperglycemia for diabetic patients. In this respect, it has been considered as a therapeutic target for the treatment of type 2 diabetes since the enzyme inhibition delays carbohydrate digestion and monosaccharide absorption and subsequently reduces postprandial plasma glucose levels. Objective: In this study, fourteen 2-(substitutedphenylamino)quinazolin-4(3H)-one derivatives were synthesized and evaluated for their α-glucosidase inhibitory activities. Methods: The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The biological activity and enzyme inhibition kinetic studies were performed by spectro-photometrical method using microplate reader. Physicochemical and drug-likeness properties of selected compounds were predicted by in silico method. Results: The biological activity results revealed that all of the synthesized compounds showed more potent α-glucosidase inhibitory activity in the range of IC50 = 58 ± 2-375 ± 15 μM when compared to the standard drug acarbose (IC50 = 892 ± 7 μM). Among the tested compounds, compound 12 bearing chlorine substituent at ortho position on N-phenyl ring displayed the highest inhibition with an IC50 value of 58 ± 2 μM against α-glucosidase. Furthermore, the enzyme inhibition kinetic study of the most active compound 12 indicated that the compound inhibited the α-glucosidase enzyme as uncompetitive with a Ki value of 63.46 μM. On the other hand, physicochemical and drug-likeness properties of selected compounds were predicted by in silico method. According to the results, it can be speculated that synthesized 2-phenylaminoquinazolin-4(3H)-one derivatives possessed favorable drug-likeness and pharmacokinetic profiles. Conclusion: In the light of results, 2-(substitutedphenylamino)quinazolin-4(3H)-one derivatives may serve as lead compounds to develop novel α-glucosidase inhibitors.

Regioselective synthesis and biological evaluation of: N -substituted 2-aminoquinazolin-4-ones

The reaction of methyl anthranilates with N-arylcyanamides in the presence of p-TsOH in t-BuOH under reflux afforded predominantly 3-arylquinazolin-4-ones. In contrast, the reaction of the same reactants with TMSCl in t-BuOH at 60 °C followed by the Dimro

I2/CHP-Mediated Oxidative Coupling of 2-Aminobenzamides and Isocyanides: Access to 2-Aminoquinazolinones

An oxidative coupling of 2-aminobenzamides 1 and isocyanides 2 mediated by I2and cumyl hydroperoxide (CHP) leads to the formation of 2-aminoquinazolinones 3 in moderate to excellent yields. This method provides an efficient approach to 2-aminoq

Ligand-free palladium assisted insertion of isocyanides to urea derivatives for cascade synthesis of phenylamino-substituted quinazolinones

Palladium catalyzed cascade coupling of substituted urea derivatives and tert-butyl isocyanide for the efficient synthesis of phenylamino-substituted quinazolinones has been developed in moderate to good yields. This method provides a short and alternative approach for the synthesis of quinazolinones derivatives which are valuable compounds with biological and pharmacological potentials. A plausible mechanistic scheme is proposed.

Continuous recycling of homogeneous Pd/Cu catalysts for cross-coupling reactions

Given the importance of homogeneous catalysts recycling in organic chemistry, we have developed a unique microfluidic loop system for automated continuous recirculation of a soluble polymer supported metal catalyst for novel isocyanide cross-coupling reactions under thermomorphic multicomponent solvent (TMS) conditions. Our system provides an innovative approach for the chemical library synthesis of quinazolinone derivatives as well as an important intermediate of Merck's LTD4 antagonist "Singulair" with efficient continuous homogeneous catalyst recycling.

Synthesis of aroylguanidines by an unexpected demethylation-addition cascade

A simple and efficient method was developed for the synthesis of N-aroyl-N′-arylguanidines under mild conditions by an unexpected demethylation-addition cascade reaction of readily available N-cyanoimidates with aryl amines. Moreover, 1-aryl-2-aminoquinazolin-4(1H)-ones and 2-(arylamino)quinazolin-4(3H)-ones can also be prepared by selective cyclization reactions of (2-fluorobenzoyl)- or (2-nitrobenzoyl)guanidines, respectively. This method provided two attractive strategies for the preparation 2-aminoquinazolinones derivatives from inexpensive reactants.

Odorless isocyanide chemistry: An integrated microfluidic system for a multistep reaction sequence

Can't smell this: An integrated continuous-flow microfluidic setup enables in situ generation, extraction, separation, and reaction of foul-smelling isocyanides with little exposure to the surroundings. Isocyanides were generated by dehydration of the corresponding N-substituted formamides, and several representative isocyanide-based organic reactions were successfully performed. DIPEA=N,N-diisopropylethylamine. Copyright