4943-82-2

Usage

InChI:InChI=1/C10H12N2O/c1-2-7-12-10(13)8-5-3-4-6-9(8)11/h2-6H,1,7,11H2,(H,12,13)

Upstream product

• 118-48-9 isatoic anhydride 
• 107-11-9 1-amino-2-propene 
• 16347-55-0 N³-allylquinazolin-4-one 
• 591-51-5 phenyllithium 
• 833-32-9 2-methyl-3-(prop-2-en-1-yl)quinazolin-4(3H)-one 
• 118-92-3 anthranilic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 2524-49-4 3-butene-1-amine 
• 28144-70-9 anthranilic acid amide 
• 106-95-6 allyl bromide 
• 5344-90-1 2-Aminobenzyl alcohol 

Downstream Products

• 1449478-06-1 3-allyl-2,3-dihydro-2-phenylbenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 88229-25-8 N-allyl-2-nitrobenzamide 
• 68614-89-1 N-allyl-2-methylaminobenzamide 
• 206271-42-3 3-allyl-2-(2-bromophenyl)-2,3-dihydroquinazolin-4(1H)-one 
• 21263-59-2 3-prop-2-en-1-yl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one 
• 1013544-47-2 C₁₇H₁₅N₃O₃ 
• 1486520-90-4 C₁₇H₁₇N₃O 
• 26060-01-5 3-allyl-2-phenylquinazolin-4(3H)-one 
• 215734-48-8 allyl 2-(triphenylphosphoranylideneamino)aminobenzoic carboxamide 
• 127144-16-5 C₁₄H₁₆ClN₃O₃ 
• 20878-50-6 2-((propylamino)methyl)aniline 
• 860724-50-1 N-formylanthranilpropenylamide 

Relevant academic research and scientific papers

Efficient synthesis of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives catalyzed by functionalized nanoporous silica

An efficient and facile method has been developed for the synthesis of various 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives, via a three-component reaction of 2-amino-N-(R)-benzamide derivatives with 2-formylbenzoic acid using sulfonic acid functionalized nanoporous silica as an efficient catalyst in ethanol under reflux. High yield of the desired products, reusability of the catalyst, and effortless workup step without using chromatography are the advantages of this method. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives

A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.

Novel quinazolin–sulfonamid derivatives: synthesis, characterization, biological evaluation, and molecular docking studies

In the design of novel drugs, the formation of hybrid molecules via the combination of several pharmacophores can give rise to compounds with interesting biochemical profiles. A series of novel quinazolin–sulfonamid derivatives (9a–m) were synthesized, characterized and evaluated for their in vitro antidiabetic, anticholinergics, and antiepileptic activity. These synthesized novel quinazolin–sulfonamid derivatives (9a–m) were found to be effective inhibitor molecules for the α-glycosidase, human carbonic anhydrase I and II (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzyme, with Ki values in the range of 100.62 ± 13.68–327.94 ± 58.21 nM for α-glycosidase, 1.03 ± 0.11–14.87 ± 2.63 nM for hCA I, 1.83 ± 0.24–15.86 ± 2.57 nM for hCA II, 30.12 ± 3.81–102.16 ± 13.87 nM for BChE, and 26.16 ± 3.63–88.52 ± 20.11 nM for AChE, respectively. In the last step, molecular docking calculations were made to compare biological activities of molecules against enzymes which are achethylcholinesterase, butyrylcholinesterase and α-glycosidase. Communicated by Ramaswamy H. Sarma.

Synthesis and biological evaluation of quinoline-quinazolinones for antimicrobial and antileishmanial potential

In an attempt to find a new class of antimicrobial and antileishmanial agents, a series of twenty-three quinoline-quinazolinones were prepared via reaction of 8-hydroxy/methoxyquinoline-2-carbaldehyde with various substituted aminobenzamides. These compounds were screened for their antimicrobial activity against Gram-positive bacteria (B. subtilis), Gram-negative bacteria (E. coli and P. putida) and fungus (C. viswanathii) and antileishmanial activity against promastigotes of L. donovani. Compound 28k exhibited highest activity against B. subtilis with an IC50 of 0.17±0.07 M while compound 28j exhibited highest activity against promastigotes of L. donovani with an IC50 of 6±0.0 M.

Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions

Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.

A facile synthesis of (Z)-1, 6-disubstituted-7H-benzo[b][1,5]diazonin-7-one derivatives via arylation-allylation-RCM pathway of anthranilamide and isatoic anhydride

A facile and efficient method has been developed for the synthesis of (Z)-6-allyl-1-phenyl-1,2,5,6-tetrahydro-7H-benzo[b][1,5]diazonin-7-one and (Z)-1,6-diphenyl-1,2,5,6-tetrahydro-7H-benzo[b][1,5]diazonin-7-one from anthranilamide via N-arylation/N-allylation and from isatoic anhydride via ring opening/N-arylation/N-allylation followed by ring closing metathesis using Grubbs-II catalyst as a key step. Grubbs-II catalyst was found to be superior over Grubbs-I catalyst in terms of reaction time and yield of the product, and the routes developed were suitable to synthesize benzo fused nine membered nitrogen heterocycles. The requirement of diallylated substrates with protected amine and amide nitrogen is suitable for RCM has been established for the synthesis of diazoninone derivatives.

Fluorocyclisation via I(I)/I(III) catalysis: A concise route to fluorinated oxazolines

Herein, we describe a catalytic fluorooxygenation of readily accessible N-allylcarboxamides via an I(I)/I(III) manifold to generate 2-oxazolines containing a fluoromethyl group. Catalysis is conditional on the oxidation competence of Selectfluor, whilst HF serves as both a fluoride source and Br?nsted acid activator. The C(sp3)–F bond of the mono-fluoromethyl unit and the C(sp3)–O bond of the ring are aligned in a synclinal relationship thereby engaging in stabilising hyperconjugative interactions with vicinal, electron-rich σ-bonds (σC–C→σ*C–F and σC–H→σ*C–O). This manifestation of the stereoelectronic gauche effect was established by X-ray crystallographic analysis of a representative example. Given the importance of fluorine in drug discovery, its ability to modulate conformation, and the prevalence of the 2-oxazoline scaffold in Nature, this strategy provides a rapid entry into an important bioisostere class.

Reducing the Flexibility of Type II Dehydroquinase for Inhibition: A Fragment-Based Approach and Molecular Dynamics Study

A multidisciplinary approach was used to identify and optimize a quinazolinedione-based ligand that would decrease the flexibility of the substrate-covering loop (catalytic loop) of the type II dehydroquinase from Helicobacter pylori. This enzyme, which i

Unusual Acid- and Base-Catalyzed C-N Bond Formation Approach through Reaction of Chromonyl Meldrum's Acid and Nitrogen Binucleophiles

Reaction of chromonyl Meldrum's acid and N-substituted 2-aminobenzamides was studied in the presence of acidic and basic catalysts. The use of methanesulfonic acid as a catalyst in this reaction led to the synthesis of chromonyl quinazolinones through employing Meldrum's acid as a carbon leaving group. However, in the presence of basic catalyst, this reaction gave functionalized 2-pyridones.

CuBr/Et3N-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-ones

A series of novel quinazolin-4(3H)-one derivatives were efficiently synthesized starting from isatoic anhydride. First, reaction of isatoic anhydride and amines in H2O at room temperature afforded 2-aminobenzamides. Then, CuBr/Et3N promoted reaction of 2-aminobenzamides and different aryl isothiocyanates in DMF at 80° afforded the title compounds in good yield.