4248-15-1

Upstream product

• 106584-45-6 2-anilino-3-aminoquinazoline-4(3H)-hydrazone 
• 106584-44-5 2-Phenylamino-3-{[1-phenyl-meth-(E)-ylidene]-amino}-3H-quinazolin-4-one 
• 626-36-8 ethyl allophanate 
• 622-16-2 1,3-Diphenylcarbodiimide 
• 62-53-3 aniline 
• 607-68-1 2,4-dichloroquinazoline 
• 3898-07-5 N-phenyl-benzamidine 
• 118-92-3 anthranilic acid 
• 54855-81-1 2-methylthioquinazolin-4(3H)-one 
• 607-69-2 2-chloro-4(3H)-quinazolinone 
• 134-20-3 2-carbomethoxyaniline 
• 622-34-4 1-phenylcyanamide 
• 615-43-0 2-iodophenylamine 
• 931-53-3 Cyclohexyl isocyanide 

Downstream Products

• 148063-17-6 4-carbethoxymethoxy-2-(N-phenylamino)quinazoline 
• 154136-78-4 5-<2'-(N-phenylamino)quinazolin-4'-yloxomethyl>-2-chloroacetyl-4-phenyl-1,2,4-triazole-3-thione 
• 154136-69-3 5-<2'-(N-phenylamino)quinazolin-4'-yloxomethyl>-4-phenyl-3-thioureido-1,2,4-triazole 
• 154136-66-0 5-<2'-(N-phenylamino)quinazolin-4'-yloxomethyl>-4-phenyl-1,2,4-triazole-3-thiol 
• 154136-65-9 2-(N-phenylamino)quinazolin-4-yloxoacetylhydrazine 

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

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.

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.

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.

Phosphonium-mediated cyclization of N-(2-aminophenyl)thioureas: Efficient synthesis of 2-aminobenzimidazoles

BOP efficiently promoted the phosphonium-mediated cyclization of thioureas, leading to a convenient synthesis of 2-aminobenzimidazoles. Compared to conventional methods, the reactions were complete at room temperature with times ranging from a few minutes

Molybdenum-mediated synthesis of quinazolin-4(3H)-ones via cyclocarbonylation using microwave irradiation

A new, efficient and practical synthesis of quinazolin-4(3H)-ones is reported via molybdenum-mediated cyclocarbonylation using microwave irradiation. These methods allow access to a wide range of quinazolin-4(3H)-ones in reasonable yields without the need for gaseous carbon monoxide and palladium catalysts. A range of reactions illustrating the wide scope of this chemistry was carried out and all proceeded in reasonable yields.

A concise and efficient solid-phase synthesis of 2-amino-4(3H)-quinazolinones

A concise and efficient solid-phase synthesis of 2-amino-4(3H)-quinazolinones is described. Reaction of polymer-bound isothiourea with isatoic anhydride provides 2-amino-4(3H)-quinazolinones with good yields and excellent purity. (C) 2000 Elsevier Science Ltd.

Synthesis of 2-aminoquinazoline-4(3H)-one derivatives as potential potassium channel openers

Starting from 2-thioxoquinazolin-4-one, the synthesis of 2-amino-4(3H)- one derivatives, structurally related to potassium channels openers pinacidil and diazoxide, is described.

Synthesis and some reactions of 5--4-phenyl-1,2,4-triazole-3-thiol

5--4-phenyl-1,2,4-triazole-3-thiol (4) has been prepared via alkylation of 2-(N-phenylamino)-4(3H)-quinazoline (1) with ethyl chloroacetate followed by condensation with hydrazine hydrate and subsequent cycliza