827006-84-8

Basic information

• Product Name: 2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE
• Synonyms: CHEMBRDG-BB 7935407;2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE;2-AMINO-N-[(4-FLUOROPHENYL)METHYL]BENZAMIDE;AKOS BBV-004290;OTAVA-BB 1133341;UKRORGSYN-BB BBV-004290;2-amino-N-(4-fluorobenzyl)benzamide(SALTDATA: FREE)
• CAS NO: 827006-84-8
• Molecular Formula: C₁₄H₁₃FN₂O
• Molecular Weight: 244.26
• Mol File: 827006-84-8.mol

Chemical Properties

• Boiling Point: 463.8°C at 760 mmHg
• Flash Point: 234.3°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 8.82E-09mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE(827006-84-8)
• EPA Substance Registry System: 2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE(827006-84-8)

Safety Data

• Hazardous Substances Data: 827006-84-8(Hazardous Substances Data)

Usage

General Description

The chemical "2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE" is a benzamide derivative with a molecular formula C14H13FN2O. It contains an amine group and a benzamide group, as well as a fluorobenzyl substituent. 2-AMINO-N-(4-FLUOROBENZYL)BENZAMIDE may have potential applications in medicinal chemistry, as benzamide derivatives have been studied for their pharmacological properties, such as anti-inflammatory and anticancer activities. The presence of the fluorobenzyl group may also impart specific chemical and biological properties to the molecule. Further research is needed to fully understand the potential uses and effects of this compound.

InChI:InChI=1/C14H13FN2O/c15-11-7-5-10(6-8-11)9-17-14(18)12-3-1-2-4-13(12)16/h1-8H,9,16H2,(H,17,18)

Upstream product

• 118-48-9 isatoic anhydride 
• 140-75-0 para-fluorobenzylamine 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 945368-81-0 3-(4-fluorobenzyl)quinazolin-2,4(1H,3H)-dione 
• 128650-86-2 [3-(4-Fluoro-benzyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetic acid 
• 128650-94-2 [3-(4-Fluoro-benzyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetic acid ethyl ester 
• 1486520-86-8 C₂₁H₁₈FN₃O 
• 1486520-87-9 C₂₂H₂₀FN₃O₂ 
• 1486520-96-0 12-(4-fluorobenzyl)-6-thioxo-11b,12-dihydro-6H-quinazolino[3,4-a]quinazolin-13(7H)-one 
• 1486520-97-1 12-(4-fluorobenzyl)-8-methoxy-6-thioxo-11b,12-dihydro-6H-quinazolino[3,4-a]quinazolin-13(7H)-one 
• 1486520-79-9 C₂₁H₁₆FN₃O₃ 
• 1486520-80-2 C₂₂H₁₈FN₃O₄ 
• 1628908-47-3 8-(4-fluorobenzyl)-1-methyl-7b,8-dihydro-9H-benzo[6,7][1,4]oxazepino[4,5-a]quinazolin-9-one 
• 1628908-48-4 6-bromo-8-(4-fluorobenzyl)-1-methyl-7bH-benzo[6,7][1,4]oxazepino[4,5-a]quinazolin-9(8H)-one 
• 1628908-39-3 8-(4-fluorobenzyl)-1-methyl-7b,8-dihydro-9H-benzo[6,7][1,4]oxazepino[4,5-a]quinazolin-9-one 
• 1628908-53-1 6-bromo-8-(4-fluorobenzyl)-1-methyl-7bH-benzo[6,7][1,4]oxazepino[4,5-a]quinazolin-9(8H)-one 
• 1618654-27-5 2-(tert-butylamino)-3-(4-fluorobenzyl)quinazolin-4(3H)-one 

Relevant articles and documents

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.

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.

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.

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.

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides

An efficient, practical approach to the copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-one derivatives is described. The preparation involves treatment of benzyl amines with benzyl anthranilamides in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide (TBAB).

An efficient metal-free synthesis of 2-amino-substituted-4(3H)-quinazolinones

2-Amino-substituted-4(3H)-quinazolinones have been synthesized via an efficient metal-free reaction between 2-aminobenzamide derivatives and carbonimidic dibromides. The reaction proceeds in the presence of K2CO3 affording cyclized products in good to excellent yields.

An efficient four-step approach toward fused triazino[1,6-a] quinazolines

Herein, we describe a simple, four-step process for the preparation of 1,2,3-triazino[1,6-a]quinazolin-13-ones. This method involves ring-opening, quinazoline-forming condensation, reduction, diazotization accompanied by rapid intramolecular cyclization in the last step afforded the desired products with structurally complex heterocyclic core in excellent to high yields.

Bridgehead Bicyclo[4.4.0]boron Heterocycles: A One-Pot Four-Component Synthesis of Dibenzo[e,i][1,3,7,2]oxadiazaborecin-8(7H)-ones

A one-pot four-component synthesis of 6-aryl-6H-dibenzo[e,i][1,3,7,2]oxadiazaborecin-8(7H)-ones is described. Heating a mixture of isatoic anhydride and a benzylamine afforded the corresponding anthranilamide derivative, which was condensed with a 2-hydroxybenzaldehyde and an arylboronic acid under solvent-free conditions to produce bridgehead bicyclo[4.4.0]-boron heterocycles in good to excellent yields. Single-crystal X-ray analysis conclusively confirms the structures of the obtained bridgehead bicyclic 6–6 heterocyclic compounds.