18543-23-2

Upstream product

• 93-97-0 benzoic acid anhydride 
• 4424-17-3 2-aminobenzanilide 
• 5165-73-1 2-phenyl-3-phenylimino-3H-indole 1-oxide 
• 116-17-6 triisopropyl phosphite 
• 1022-46-4 2-phenyl-4H-3,1-benzoxazin-4-one 
• 62-53-3 aniline 
• 10282-57-2 2-bromobenzanilide 
• 55-21-0 benzamide 
• 579-93-1 2-(Benzoylamino)benzoic Acid 
• 98-88-4 benzoyl chloride 
• 118-92-3 anthranilic acid 
• 150256-42-1 2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid 
• 1352126-54-5 Fmoc-2-aminobenzoic acid 
• 108-88-3 toluene 

Downstream Products

• 22686-82-4 2,3-diphenyl-3H-quinazolin-4-one 
• 53007-52-6 N-(2-phenyl-4H-3,1-benzoxazin-4-ylidene)benzenamine 

Relevant academic research and scientific papers

Recyclable keggin heteropolyacids as an environmentally benign catalyst for the synthesis of new 2-benzoylamino-n-phenyl-benzamide derivatives under microwave irradiations at solvent-free conditions and the evaluation of biological activity

2-Benzoylamino-N-phenyl-benzamide derivatives (5a–h) were prepared from 2-phenyl-3,1-(4H)-benzoxazin-4-one 3 and substituted anilines 4a–h in the presence of a Keggin-type heteropolyacids series (H3PW12O40·13H2O

ANTIVIRAL COMPOUNDS

The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.

Synthesis, biological evaluation, and structure-activity relationships of 2-[2-(benzoylamino)benzoylamino]benzoic acid analogues as inhibitors of adenovirus replication

2-[2-Benzoylamino)benzoylamino]benzoic acid (1) was previously identified as a potent and nontoxic antiadenoviral compound (Antimicrob. Agents Chemother. 2010, 54, 3871). Here, the potency of 1 was improved over three generations of compounds. We found that the ortho, ortho substituent pattern and the presence of the carboxylic acid of 1 are favorable for this class of compounds and that the direction of the amide bonds (as in 1) is obligatory. Some variability in the N-terminal moiety was tolerated, but benzamides appear to be preferred. The substituents on the middle and C-terminal rings were varied, resulting in two potent inhibitors, 35g and 35j, with EC50 = 0.6 μM and low cell toxicity.

Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation

CuI/4-hydroxy-l-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 °C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.

NEW ANTIVIRAL COMPOUNDS

The present invention provides new antiviral compounds and pharmacological compositions comprising these new compounds and their use in the prophylaxis, prevention and treatment of viral infections, particularly adenovirus and herpes virus infections.

Synthesis and anti-inflammatory activity of 2,3-diaryl-4(3H)-quinazolinones

2,3-Diaryl-4(3H)-quinazolinones containing various substituents on diaryl rings have been synthesized and evaluated for their cyclooxygenase-2 inhibitory activity by the colorimetric COX (ovine) inhibitor screening assay and anti-inflammatory activity by the carrageenan-induced rat paw edema assay. 2-(4-Nitrophenyl)-3-(4-tolyl)-4(3H)-quinazolinone showed a maximum COX-2 inhibition of 27.72% at 22 μM concentration in the present series and exhibited a mild anti-inflammatory activity at a dose of 50 mg/kg in carrageenan-induced rat paw edema assay.

New insights on the reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: An indolic nitrone. Crystal structures of 1-diethylphosphoryl-2-phenyl-3-phenylamino-1H-indole and 2-phenyl-4-phenylimino-4H-3,1-benzoxazine

2-Phenyl-3-phenylimino-3H-indole N-oxide (an indolic nitrone) reacts with triethyl and triisopropyl phosphite in refluxing xylene and tert-butylbenzene to give 2-phenyl-3-phenylimino-3H-indole (indolenine) in very good yield. The same reaction carried out in refluxing phosphite gave rise to a series of compounds which in part derive from the thermal rearrangement of the starting nitrone and in part from the interaction of the indolenine with phosphites. The formation of the products arising from the reduction of the indolenine is explained by an electron transfer process between this intermediate and the phosphite; whereas the formation of the phosphorylated products is interpreted through the evolution of the intermediate zwitterion generated by the nucleophilic attack of the phosphite on carbon-2 of the indolenine. The formation of this intermediate is also discussed in terms of an electron transfer process. Crystal structures of 1-diethylphosphoryl-2-phenyl-3-phenylamino-1H-indole and 2-phenyl-4-phenylimino-4H-3,1-benzoxazine are also described.

Synthesis and Rearrangement of 4-Imino-4H-3,1-benzoxazines

N-Acylanthranilamides react with dibromotriphenylphosphorane in the presence of triethylamine as HBr captor to give 4-imino-4H-3,1-benzoxazines in good yields.If the reaction is carried out without acid acceptor, N-acetylanthranilamides yield 2-methyl-4-q

One-Pot Synthesis of 2,3-Disubstituted Quinazolin-4-ones

Whereas the condensation of N-acetylanthranilic acid (1a) with methyl and phenyl isothiocyanates (2) affords the corresponding 3-substituted 2-methylquinazolin-4-ones (7, R1=Me), N-benzoylanthranilic acid (1b) reacts with these isothiocyanates to give 2-phenyl-3,1-benzoxazin-4-one (5b: R1=Ph) and N-substituted o-benzoylaminobenzamide (6: R1=R2=Ph), respectively.

Condensation of 2-Methyl-3,1-benzoxazin-4-one with Schiff Bases: Simultaneous Introduction of Arylidene and Amine Moieties

2-Methyl-3,1-benzoxazin-4-one (3), generated by cyclising N-acetylanthranilic acid with ethyl chloroformate in benzene containing triethylamine, reacts with schiff bases in situ when heated under reflux in gl. acetic acid to give 3-substituted 2-styryl-3,4-dihydro-4-quinazolones (7).