4943-83-3

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-N-(2-PROPYNYL)BENZENECARBOXAMIDE is used as a building block for the synthesis of new organic compounds, contributing to the development of innovative pharmaceutical drugs. Its unique structure and functional groups make it a valuable component in the creation of novel therapeutic agents.
Used in Research Applications:
In the research field, 2-AMINO-N-(2-PROPYNYL)BENZENECARBOXAMIDE is used as a starting material for the production of pharmaceutical drugs. Its properties and reactivity allow for the exploration of new chemical reactions and the synthesis of potential drug candidates, advancing the understanding of medicinal chemistry.
Used in Material Development:
2-AMINO-N-(2-PROPYNYL)BENZENECARBOXAMIDE is utilized in the development of new materials, leveraging its chemical properties to create innovative substances with unique characteristics. Its potential applications in material science could lead to the discovery of new materials with improved properties for various industries.
Used in Biomedical Research:
In biomedical research, 2-AMINO-N-(2-PROPYNYL)BENZENECARBOXAMIDE is employed for its potential applications in the development of new diagnostic tools, therapeutic agents, and other biomedical technologies. Its involvement in this field could contribute to advancements in healthcare and medical treatments.

InChI:InChI=1/C10H10N2O/c1-2-7-12-10(13)8-5-3-4-6-9(8)11/h1,3-6H,7,11H2,(H,12,13)

Upstream product

• 118-48-9 isatoic anhydride 
• 2450-71-7 Propargylamine 
• 1246999-28-9 2-(4-hydroxy-phenylazo)-N-(prop-2-ynyl)benzamide 
• 53007-15-1 2-nitro-N-(prop-2-ynyl)benzamide 
• 118-92-3 anthranilic acid 
• 5344-90-1 2-Aminobenzyl alcohol 

Downstream Products

• 16347-56-1 3-(prop-2-yn-1-yl)quinazolin-4(3H)-one 
• 52829-71-7 2-(2-aminophenyl)-5-methyloxazole 
• 823235-08-1 acetic acid (2-prop-2-ynylcarbamoylphenylcarbamoyl)methyl ester 
• 1384487-71-1 16a-phenyl-16,16a-dihydrobenzo[5,6][1,2,3]triazolo[5',1':3,4][1,4]diazepino[7,1-b]quinazolin-11(9H)-one 
• 1384487-72-2 C₂₃H₁₆ClN₅O 

Relevant academic research and scientific papers

Effects Of 2-Methyl-3-propynylquinazolin-4-(3H)-one On Vascular Reactivity in Isolated Porcine Tail Arteries

The vascular effects of 2-methyl-3-propynylquinazolin-4-(3H)-one (QUIN) have been studied on isolated porcine tail arteries. QUIN had no effect on resting tension but relaxed, dose-dependently, arteries precontracted with noradrenaline or high-K+/su

Synthesis and anti-acetylcholinesterase activity of benzotriazinone-triazole systems

An approach for the construction of benzotriazinone-triazole system is described. The synthesis is based on diazonium chemistry and subsequent intramolecular heteroatom-heteroatom bond formation. The introduction of triazole moiety occurred via click reac

Synthesis of Novel Isoindolo[2,1-a]quinazolinedione Derivatives Containing a 1,2,3-Triazole Ring System

A synthesis of isoindolo[2,1-a]quinazolinedione derivatives, coupled with a 1,2,3-triazole ring system, via the reaction of isatoic anhydride, HC=CCH2NH2, and 2-formylbenzoic acid is described, which led to the formation of the isoin

Quinazolinone [2, 3 - a] carboline derivative as well as preparation method and application thereof

The main content of the invention is to provide a new quinazolinone [2, 3 - a] carboline compound as well as a preparation method and application thereof, and has the quinazolinone of the general formula (I) and [2, 3 - a] carboline compounds. A quinazolo

Synthesis, in vitro and computational studies of novel glycosyl-1, 2, 3-1H-triazolyl methyl benzamide derivatives as potential α-glucosidase inhibitory activity

A series of novel glycosyl-1,2,3-1H-triazolyl methyl benzamide analogues were synthesized by the unambiguous strategy and evaluated for α-glucosidase inhibitory activity. Glycosyl benzamide exhibited a dose-dependent inhibition of α-glucosidase activity.

Design, Synthesis and Biological Evaluation of Novel Anthraniloyl-AMP Mimics as PQS Biosynthesis Inhibitors against Pseudomonas aeruginosa Resistance

The Pseudomonas quinolone system (PQS) is one of the three major interconnected quorum sensing signaling systems in Pseudomonas aeruginosa. The virulence factors PQS and HHQ activate the transcription regulator PqsR (MvfR), which controls several activiti

Synthesis and antimicrobial activity of novel 1,2,3-triazole-conjugates of quinazolin-4-ones

A novel series of diethyl{4-[(4-oxoquinazolin-3(4H)-yl)methyl]-1H-1,2,3-triazol-1-yl}alkylphosphonates 9aa–aj and their respective derivatives substituted at C6 of the quinazolinone moiety with a bromine atom (9ba–bj) or a nitro group (9ca–cj) were synthesized and assessed for the antibacterial activity toward selected Gram-positive and Gram-negative bacteria. Their antifungal activity was also screened. Compound 9ac was found to be the most active against Staphylococcus aureus ATCC 6535 (MIC 0.625 mg/mL, MBC 1.25 mg/mL), phosphonates 9ab–ai showed promising activity against Enterococcus faecalis ATCC 29212 (MIC = 0.625 mg/mL, MBC = 1.25 mg/mL), while compounds 9ac–j appeared the most active toward Pseudomonas aeruginosa ATCC 27853 (MIC = 0.625 mg/mL, MBC = 1.25 mg/mL). Antifungal assays of compounds 9aa–aj, 9ba–bj, and 9ca–cj were conducted on Candida albicans ATCC 10231 and Aspergillus brasiliensis ATCC 16404 and revealed noticeable activity of 9aa–aj (MIC = 1.25 mg/mL).

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.

Glycosyl triazoles as novel insect β-N-acetylhexosaminidase OfHex1 inhibitors: Design, synthesis, molecular docking and MD simulations

The insect enzyme GH20 β-N-acetyl-D-hexosaminidase OfHex1 represents an important chitinolytic enzyme found in the agricultural pest Ostrinia furnacalis (Guenée) and inhibition of this enzyme has been considered a promising strategy for the development of eco-friendly pesticides. In this article, based on the structure of the catalytic domains of OfHex1, a series of novel glycosyl triazoles were designed and synthesized via Cu-catalyzed azide-alkyne [3+2] cycloaddition reaction. To investigate the potency and selectivity of these glycosyl triazoles, the inhibition activities towards OfHex1 and HsHexB (human β-N-acetylhexosaminidase B) were studied. Particularly compound 17c (OfHex1, Ki = 28.68 μM; HsHexB, Ki > 100 μM) exhibited a suitable activity and selectivity against OfHex1. Furthermore, the possible inhibitory mechanisms of 17c with OfHex1 were studied using molecular docking and MD simulations. The structure-activity relationship results as well as the formed binding patterns may provide promising insights into the further development of novel OfHex1 inhibitors.

Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles to Prepare Rutaecarpine Derivatives

An efficient method to synthesize rutaecarpine derivatives via the gold-catalyzed selective cyclization of alkyn-tethered indoles under mild conditions is described. The alkyn-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation. Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp3 and sp2 hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride.