5471-20-5

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-N-BENZYL-BENZAMIDE is used as a chemical intermediate for the synthesis of various pharmaceuticals, leveraging its structural properties to contribute to the development of new drugs and therapeutic agents.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 2-AMINO-N-BENZYL-BENZAMIDE is utilized as a key component in the synthesis of a range of organic compounds, highlighting its importance in creating complex molecular structures.
Used in Research and Development:
2-AMINO-N-BENZYL-BENZAMIDE is employed in research and development settings as a building block for the creation of novel biologically active molecules, potentially leading to breakthroughs in medicine and other scientific disciplines.
Used in Specialty Chemicals Production:
2-AMINO-N-BENZYL-BENZAMIDE also finds application in the production of specialty chemicals, where its unique properties are harnessed to create high-value products for specific industrial applications.

InChI:InChI=1/C14H14N2O/c15-13-9-5-4-8-12(13)14(17)16-10-11-6-2-1-3-7-11/h1-9H,10,15H2,(H,16,17)

Upstream product

• 118-48-9 isatoic anhydride 
• 100-46-9 benzylamine 
• 87-25-2 2-ethoxycarbonylaniline 
• 5632-37-1 1-(quinazolin-4(3H)-on-3-yl)-propan-2-one 
• 55668-30-9 2-aminobenzoic acid 2,5-dioxopyrrolidin-1-yl ester 
• 76854-94-9 N-(o-Aminobenzoyloxy)-phthalimide 
• 552-16-9 ortho-nitrobenzoic acid 
• 491-36-1 4-Hydroxyquinazoline 
• 118-92-3 anthranilic acid 
• 13185-09-6 1-benzyl-3-indazolol sodium salt 
• 109632-73-7 1,2-dibenzylindazolin-3-one 
• 609-67-6 2-Iodobenzoyl chloride 
• 271-58-9 anthranil 
• 16285-33-9 2,3-dihydro-2-phenyl-3-(phenylmethyl)-4(1H)-quinazolinone 

Downstream Products

• 1026034-38-7 N-(2-Benzylcarbamoyl-phenyl)-N'-benzyloxy-2-isobutyl-malonamide 
• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 40132-09-0 3-benzyl-1,2,3,4-tetrahydro-quinazoline 
• 65992-19-0 ethyl 2-[2-(N-benzylcarbamoyl)anilino]-acetate 
• 945324-74-3 3′‐benzyl‐1′H‐spiro[indoline‐3,2′‐quinazoline]‐2,4′(3′H)‐dione 
• 1171537-61-3 C₂₄H₂₉N₃O₃ 
• 1221177-04-3 C₃₄H₃₂N₄O₂ 
• 1354196-51-2 C₂₀H₁₈N₂OS 
• 1446789-88-3 3-benzyl-2-(cyclohexylamino)quinazolin-4(3H)-one 
• 383149-00-6 6-benzyl-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione 
• 19857-37-5 3-benzyl-2-phenyl-3,4-dihydroquinazolin-4-one 
• 1628908-46-2 8-benzyl-1-methyl-7b,8-dihydro-9H-benzo[6,7][1,4]oxazepino[4,5-a]quinazolin-9-one 
• 1628908-38-2 8-benzyl-1-methyl-7b,8-dihydro-9H-benzo[6,7][1,4]oxazepino[4,5-a]quinazolin-9-one 
• 1618654-25-3 3-benzyl-2-(tert-butylamino)quinazolin-4(3H)-one 

Relevant academic research and scientific papers

Synthesis and anion recognition studies of new ureylbenzamide-based receptors

A new group of ureylbenzamide-based receptors (1–4) has been synthesized; its binding affinity and capacity to form supramolecular complexes in solution with different anions have been investigated. For designing these receptors, it was considered a combination of the positions of the urea and amide groups (ortho and meta), and the chromophore groups naphthyl and nitrophenyl, yielding four receptors. The position and chromophore structure affected the acidity of the urea and amide hydrogens in the order 4>3>2>1. All the spectroscopic studies showed a significant change of 1 and 2 compared with 3 and 4 in the presence of different TBAX salts in acetonitrile. The 1H-NMR spectra show a preferential interaction of the anions with the urea group in receptors 1 and 2 due to the less steric hindrance, while there is a cooperative interaction of amide group in receptors 3 and 4 due to the closeness of both groups.

UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.

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.]

Palladium-catalyzed atroposelective coupling-cyclization of 2-isocyanobenzamides to construct axially chiral 2-aryl- And 2,3-diarylquinazolinones

A palladium-catalyzed imidoylative cycloamidation of N-alkyl-2-isocyanobenzamides with 2,6-disubstituted aryl iodides, affording unprecedented axially chiral 2-arylquinazolinones, has been developed with good yields and atroposelectivities. In this coupling-cyclization process, the biaryl linkage and the heteroaromatic ring are formed sequentially in one step. When N-(2,4dimethoxyphenyl)-2-isocyanobenzamide is applied as a substrate, 2,3-diarylquinazolinones containing two stereogenic axes are produced with moderate diastereoselectivity and good enantioselectivities.

Palladium-catalyzed synthesis of novel trifluoromethylated quinazolinone, N-arylquinazoline and N-benzylquinazoline derivatives

A simple and palladium-catalyzed procedure for synthesis of a novel series of potentially biologically active trifluoromethyl-substituted quinazolinones and N-arylquinazoline derivatives via condensation-cyclization reaction of 2-aminobenzamide, 2-amino-N′-arylbenzimidamides and 2-amino-N′-benzylbenzimidamides with trifluoroacetimidoyl chlorides has been developed. noteworthy, this investigation showed the possible of transition-metal-catalyzed activation of trifluoroacetimidoyl chlorides as a carbon trifluoromethylated source for the synthesis of quinazolines and quinazolinone derivatives in good to excellent yields.

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.

Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives

Twenty 2,3-disubstituted quinazolin-4(3H)-one derivatives 1–20 were successfully synthesized in moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2, 3, and 20 possessed moderate activities against MCF-7 cells (IC50 = 47.2 μM, 43.9 μM, and 44.9 μM, respectively). Good cytotoxic activities against A549 cells were observed for 3 and 8 with IC50 values of 30.7 μM and 29.8 μM, respectively, which were comparable to the positive control, 5-fluorouracil (5-FU, IC50 = 27.9 μM). Furthermore, compound 4 exhibited slightly stronger activity (IC50 = 23.6 μM) than the positive control 5-FU against the A549 cell line.

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.