19050-62-5

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-N-PHENETHYL-BENZAMIDE is used as a chemical intermediate for the synthesis of various drugs. Its unique structure allows for the development of new pharmaceutical compounds with potential therapeutic benefits.
Used in Medicinal Chemistry Research:
2-AMINO-N-PHENETHYL-BENZAMIDE is utilized as a subject of investigation for its potential pharmacological properties. Its effects on the central nervous system and its potential as an anticancer agent make it a valuable compound for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C15H16N2O/c16-14-9-5-4-8-13(14)15(18)17-11-10-12-6-2-1-3-7-12/h1-9H,10-11,16H2,(H,17,18)

Upstream product

• 118-48-9 isatoic anhydride 
• 64-04-0 phenethylamine 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 91-56-5 indole-2,3-dione 
• 612-25-9 2-Nitrobenzyl alcohol 
• 100-42-5 styrene 
• 28144-70-9 anthranilic acid amide 

Downstream Products

• 4059-71-6 3-(2-phenylethyl)quinazoline-2,4(1H,3H)-dione 
• 1221177-08-7 C₃₆H₃₆N₄O₂ 
• 1385789-97-8 1-acetyl-3'-phenylethyl-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione 
• 1385790-10-2 2-((1-acetyl-3-hydroxy-2-oxoindolin-3-yl)amino)-N-phenethylbenzamide 
• 23942-46-3 2,3,3a,4-tetrahydro-3a-methyl-4-phenethylpyrrolo[1,2-a]quinazoline-1,5-dione 
• 23942-39-4 3a-methyl-4-phenethyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one 
• 141306-02-7 3-[2-(phenylethyl)]-3H-quinazolin-4-one 
• 1542098-54-3 2-(5-ethylthiophen-2-yl)-3-phenethyl-2,3-dihydroquinazolin-4(1H)-one 
• 691380-14-0 3-phenethyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one 
• 19007-80-8 1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 19260-06-1 1-(2-aminophenyl)-3,4-dihydroisoquinoline 
• 75652-62-9 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione 
• 870672-32-5 2-isocyano-N-phenethylbenzamide 

Relevant academic research and scientific papers

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.

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.

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.

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones

N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.

Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides

We investigated a base-promoted protocol for the intermolecular anti-Markovnikov hydroamidation of vinyl arenes with arylamides to furnish the arylethylbenzamides with excellent chemo- and regioselectivity. The reaction tolerates an extensive variety of functional groups and has been successfully extended with electronically varied handles, aminobenzamides, electron-rich/electron-deficient heterocyclic amides, and vinyl arenes to afford the hydroamidated products. Excellent chemoselectivity was observed for the amide group over amine. The proposed mechanism and vital role of the solvent was well supported by deuterium labeling studies and control experiments.

1,3,4-OXADIAZOLE HOMOPHTHALIMIDE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to novel compounds having a histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, a medicinal use thereof, and a method for preparing the same. The novel compounds according to the present invention, stereoisomers thereof or pharmaceutically acceptable salts thereof have the histone deacetylase 6 (HDAC6) inhibitory activity, and are effective in preventing or treating HDAC6-related diseases, comprising infectious diseases; neoplasm; endocrinopathy; nutritional and metabolic diseases; mental and behavioral disorders; neurological diseases; eye and ocular adnexal diseases; circulatory diseases; respiratory diseases; digestive diseases; skin and subcutaneous tissue diseases; musculoskeletal system and connective tissue diseases; and teratosis or deformities, or chromosomal aberration.

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is

Synthesis, Evaluation and Proposed Binding Pose of Substituted Spiro-Oxindole Dihydroquinazolinones as IRAP Inhibitors

Insulin-regulated aminopeptidase (IRAP) is a new potential macromolecular target for drugs aimed for treatment of cognitive disorders. Inhibition of IRAP by angiotensin IV (Ang IV) improves the memory and learning in rats. The majority of the known IRAP inhibitors are peptidic in character and suffer from poor pharmacokinetic properties. Herein, we present a series of small non-peptide IRAP inhibitors derived from a spiro-oxindole dihydroquinazolinone screening hit (pIC50 5.8). The compounds were synthesized either by a simple microwave (MW)-promoted three-component reaction, or by a two-step one-pot procedure. For decoration of the oxindole ring system, rapid MW-assisted Suzuki-Miyaura cross-couplings (1 min) were performed. A small improvement of potency (pIC50 6.6 for the most potent compound) and an increased solubility could be achieved. As deduced from computational modelling and MD simulations it is proposed that the S-configuration of the spiro-oxindole dihydroquinazolinones accounts for the inhibition of IRAP.

Design and synthesis of novel quinazolinone-1,2,3-triazole hybrids as new anti-diabetic agents: In vitro α-glucosidase inhibition, kinetic, and docking study

A novel series of quinazolinone-1,2,3-triazole hybrids 10a-p were designed, synthesized, and evaluated for their in vitro α-glucosidase inhibitory activity leading to efficient anti-diabetic agents. All synthesized compounds exhibited good inhibitory acti

Sulfur-Promoted Synthesis of 2-Aroylquinazolin-4(3H)-ones by Oxidative Condensation of Anthranilamide and Acetophenones

A sulfur-promoted three-component reaction of isatoic anhydride, primary aliphatic or aromatic amines, and acetophenones leading to densely substituted 3-substituted 2-aroylquinazolin-4(3H)-ones is reported. The key step involves a cascade reaction of selective oxidation of the methyl group of the acetophenones, followed by a condensation with anthranilamides. The scope of the reaction is applicable to the synthesis of tryptanthrin and various 3-unsubstituted 2-aroylquinazolin-4(3H)-ones. (Figure presented.).