56814-10-9

Usage

Uses

Used in Pharmaceutical Research:
2-Amino-N-propyl-benzamide is used as a starting material for the synthesis of potential drug candidates due to its chemical structure and pharmacological properties.
Used in Pain Relief Medications:
In the field of pain management, 2-Amino-N-propyl-benzamide is used as an analgesic agent for its pain-relieving properties, offering a potential alternative for the development of new medications to treat various types of pain.
Used in Neurodegenerative Disorder Treatment:
2-Amino-N-propyl-benzamide is considered for use as a therapeutic agent in the treatment of neurodegenerative disorders, given its potential to impact the progression of such conditions.
Used in Psychiatric Condition Treatment:
2-AMINO-N-PROPYL-BENZAMIDE is also being explored for its potential applications in the treatment of psychiatric conditions, suggesting a broader scope of therapeutic uses beyond pain management and neurodegenerative diseases.

InChI:InChI=1/C10H14N2O/c1-2-7-12-10(13)8-5-3-4-6-9(8)11/h3-6H,2,7,11H2,1H3,(H,12,13)

Upstream product

• 107-10-8 propylamine 
• 118-48-9 isatoic anhydride 
• 118-92-3 anthranilic acid 
• 91-56-5 indole-2,3-dione 
• 21563-73-5 2-aminobenzoyl chloride 
• 5344-90-1 2-Aminobenzyl alcohol 
• 68790-38-5 2-(tert-butyloxycarbonylamino)benzoic acid 
• 1022964-01-7 2-(propylcarbamoyl-phenyl)-carbamic acid tert-butyl ester 

Downstream Products

• 417715-41-4 N-propyl-2-(2-hydroxyethyl)aminobenzoic amide 
• 417715-48-1 1-(2-bromo-ethyl)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-2λ⁵-benzo[1,3,2]diazaphosphinine-2-carboxylic acid phenylamide 
• 417715-52-7 1-(2-bromo-ethyl)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-2λ⁵-benzo[1,3,2]diazaphosphinine-2-carboxylic acid p-tolylamide 
• 417715-50-5 1-(2-bromo-ethyl)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-2λ⁵-benzo[1,3,2]diazaphosphinine-2-carboxylic acid (4-chloro-phenyl)-amide 
• 417715-54-9 1-(2-bromo-ethyl)-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-2λ⁵-benzo[1,3,2]diazaphosphinine-2-carboxylic acid (4-nitro-phenyl)-amide 
• 815654-41-2 4-oxo-4-{{2-[(propylamino)carbonyl]phenyl}amino}butanoic acid 
• 1158553-50-4 2-oxo-2-{{2-[(propylamino)carbonyl]phenyl}amino}acetic acid 
• 1022964-12-0 2-[5-chloro-2-(1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-propyl-benzamide 
• 1022964-04-0 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-propyl-benzamide 
• 1385790-22-6 2-((1-acetyl-3-hydroxy-2-oxoindolin-3-yl)amino)-N-(n-propyl)benzamide 
• 26060-02-6 2-phenyl-3-n-propylquinazoline-4(3H)-one 
• 63586-34-5 3‐propyl‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one 

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.]

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.

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.

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

A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones

A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.

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.

Synthesis and anion recognition studies of new oligomethylene bis(nitrophenylureylbenzamide) receptors

A new series of oligomethylene bis(nitrophenylureylbenzamide) receptors were synthesized varying the relative position of the urea and amide groups (ortho4 and meta8) and the length of the oligomethylene chain (C2 to C8). An anion re

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.