246231-75-4

Upstream product

• 4083-64-1 Tosyl isocyanate 
• 51031-91-5 (Z)-N'-(3-methoxyphenyl)benzimidamide 
• 103-71-9 phenyl isocyanate 
• 1224442-31-2 N-[imino(phenyl)methyl]-4-methoxy-2-nitrobenzamide 
• 38487-91-1 2-amino-p-anisamide 
• 100-51-6 benzyl alcohol 
• 74317-85-4 2-bromo-4-methoxybenzoic acid 
• 1670-14-0 benzamidine monohydrochloride 
• 1452311-14-6 (Z)-N'-hydroxy-N-(4-methoxybenzyl)benzimidamide 
• 932-90-1 Benzaldoxime 
• 698-16-8 benzohydroximoyl chloride 
• 1520077-98-8 2-amino-N,4-dimethoxybenzamide 
• 100-52-7 benzaldehyde 
• 52351-75-4 6-methoxyisatin 

Downstream Products

• 923274-29-7 (1R,2R,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl ester 
• 923274-31-1 (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate 
• 923274-30-0 (1R,2R,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid 
• 371946-85-9 4-oxo-2-phenyl-3,4-dihydroquinazolin-7-yl acetate 

Relevant academic research and scientific papers

Structure-based drug design: Synthesis and biological evaluation of quinazolin-4-amine derivatives as selective Aurora A kinase inhibitors

Aurora kinases play critical roles in the regulation of the cell cycle and mitotic spindle assembly. Aurora A kinase, a member of the Aurora protein family, is frequently highly expressed in tumors, and selective Aurora A inhibition serves as a significant component of anticancer therapy. However, designing highly selective Aurora A inhibitors is difficult because Aurora A and B share high homology and differ only by three residues in their ATP-binding pockets. Through structure-based drug design, we designed and synthesized a series of novel quinazolin-4-amine derivatives. These derivatives act as selective Aurora A kinase inhibitors by exploiting the structural differences between Aurora A and B. The selectivities of most compounds were improved (the best up to >757-fold) when comparing with the lead compound (3-fold). In vitro biochemical and cellular assays revealed that compound 6 potently inhibited Aurora A kinase and most human tumor cells. Furthermore, compound 6 effectively suppressed carcinoma, such as triple-negative breast cancers (TNBC) in an animal model. Therefore, compound 6 might serve as a promising anticancer drug. Moreover, through molecular dynamic (MD) analysis, we have identified that a salt bridge formed in Aurora B is key contributor for the isoform selectivity of the inhibitor. This salt bridge has not been previously detected in the reported crystal structure of Aurora B. These results might provide a crucial basis for the further development of highly potent inhibitors with high selectivity for Aurora A.

Divergent Synthesis of Quinazolin-4(3H)-ones and Tryptanthrins Enabled by a tert-Butyl Hydroperoxide/K3PO4-Promoted Oxidative Cyclization of Isatins at Room Temperature

A synergetic tert-butyl hydroperoxide/K3PO4-promoted oxidative cyclization has been developed for the facile synthesis of various functionalized quinazolin-4(3H)-ones from commercially available isatins and amidine hydrochlorides at room temperature. The synthetic utility of this strategy was illustrated by the convenient synthesis of tryptanthrin derivatives via a self-dimerization of isatins under the same conditions.

Oxidant- and metal-free synthesis of 4(3H)-quinazolinones from 2-amino-N-methoxybenzamides and aldehydes via acid-promoted cyclocondensation and elimination

A series of biologically important 4(3H)-quinazolinones were readily synthesized in good to excellent yields from 2-amino-N-methoxybenzamides and aldehydes via a cascade reaction consisting of AcOH-promoted cyclocondensation and elimination. The current m

Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones

Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60°C under an O 2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes

Fe3O4 nanoparticle-supported copper(I): Magnetically recoverable and reusable catalyst for the synthesis of quinazolinones and bicyclic pyrimidinones

A highly efficient, easily recoverable and reusable Fe3O 4 magnetic nanoparticle-supported Cu(I) catalyst has been developed for the synthesis of quinazolinones and bicyclic pyrimidinones. In the presence of supported Cu(I) catalyst (10 mol%), amidines reacted with substituted 2-halobenzoic acids and 2-bromocycloalk-1-enecarboxylic acids to generate the corresponding N-heterocycle products in good to excellent yields at room temperature in DMF. In addition, the supported Cu(I) catalyst could be recovered at least 10 times without significant loss of its catalytic activity. Copyright

One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers

A one-pot oxidative cyclization of primary alcohols with o-aminobenzamides to quinazolinones was successfully achieved using [Cp*IrCl 2]2 (Cp* = pentamethylcyclopentadienyl) as a catalyst under hydrogen transfer conditions.

Synthesis of quinazolin-4(3H)-ones via Pd(II)-catalyzed intramolecular C(sp2)-H carboxamidation of N-arylamidines

An efficient synthesis of quinazolin-4(3H)-ones from N-arylamidines, through palladium-catalyzed intramolecular C(sp2)-H carboxamidation, has been developed. The reaction, carried out in the presence of 1.0 equiv of CuO as oxidant under atmospheric pressure of CO, provides diversified 2-aryl(alkyl)quinazolin-4(3H)-ones in reasonable to good yields from N-arylamidines, which are readily derived from anilines and nitriles. Compared with existing approaches to quinazolin-4(3H)-ones, the current strategy features atom-economy and step-efficiency.

Catalyst/ligand-free synthesis of benzimidazoles and quinazolinones from amidines via intramolecular transamination reaction

An efficient catalyst/ligand-free synthesis of benzimidazoles and quinazolinones from amidines in quantitative yields has been described.

Synthesis and SAR of potent inhibitors of the Hepatitis C virus NS3/4A protease: Exploration of P2 quinazoline substituents

Novel NS3/4A protease inhibitors comprising quinazoline derivatives as P2 substituent were synthesized. High potency inhibitors displaying advantageous PK properties have been obtained through the optimization of quinazoline P2 substituents in three series exhibiting macrocyclic P2 cyclopentane dicarboxylic acid and P2 proline urea motifs. For the quinazoline moiety it was found that 8-methyl substitution in the P2 cyclopentane dicarboxylic acid series improved on the metabolic stability in human liver microsomes. By comparison, the proline urea series displayed advantageous Caco-2 permeability over the cyclopentane series. Pharmacokinetic properties in vivo were assessed in rat on selected compounds, where excellent exposure and liver-to-plasma ratios were demonstrated for a member of the 14-membered quinazoline substituted P2 proline urea series.

Macrocylic Inhibitors of Hepatitis C Virus

Compounds of the formula I: and N-oxides, salts, and stereoisomers thereof wherein A is OR1, NHS(═O)pR2; wherein; R1 is hydrogen, C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl;R2 is C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkyleneheterocyclyl;p is independently 1 or 2;n is 3, 4, 5 or 6; — denotes an optional double bond;L is N or CRz; Rz is H or forms a double bond with the asterisked carbon;Rq is H or when L is CRz, Rq can also be C1-C6alkyl;Rr is quinazolinyl, optionally substituted with one two or three substituents each independently selected from C1-C6 alkyl, C1-C6alkoxy, hydroxyl, halo, haloC1-C6alkyl, amino, mono- or dialkylamino, mono- or dialkylaminocarbonyl, C1-C6alkyl-carbonylamino, C0-C3alkylenecarbocyclyl and C0-C3 alkyleneheterocyclyl;R5 is hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C6alkyl or C3-C7cycloalkyl;R6 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl, hydroxy, bromo, chloro or fluoro have utility in the treatment or prophylaxis of flaviviral infections such as HCV