16347-56-1

Upstream product

• 4943-83-3 2-amino-N-(prop-2-yn-1-yl)benzamide 
• 122-51-0 orthoformic acid triethyl ester 
• 108160-14-1 4-(2-propynyloxy)quinazoline 
• 118-48-9 isatoic anhydride 
• 5632-36-0 2,3-dihydro-4(1H)-quinazolinone 
• 83-34-1 3-Methylindole 
• 2450-71-7 Propargylamine 
• 123-91-1 1,4-dioxane 
• 107-19-7 propargyl alcohol 
• 107-21-1 ethylene glycol 
• 106-96-7 propargyl bromide 
• 491-36-1 4-quinazolinol 
• 118-92-3 anthranilic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 5221-67-0 5-methyl-2-phenyloxazole 
• 52829-71-7 2-(2-aminophenyl)-5-methyloxazole 
• 1449434-89-2 3-((1-(2,3,5-tri-O-benzoyl-β-D-ribofuranos-1-yl)-1,2,3-triazol-4-yl)methyl)quinazolin-4-one 
• 25379-67-3 N-[2-(5-methyl-oxazol-2-yl)-phenyl]-formamide 

Relevant academic research and scientific papers

Microwave-assisted [3+2] cycloaddition and suzuki-miyaura cross-coupling for a concise access to polyaromatic scaffolds

Novel 3-(prop-2-ynyl)pyrido[2,3-d]pyrimidin-4(3H)-ones and 3-(prop-2-ynyl)quinazolin-4(3H)-ones have been synthesized in a high-yielding microwave-assisted one-pot procedure. The one-pot sequence was conveniently extended to the synthesis of commercially unavailable 6-bromo-N 3-propargylpyrido[2,3-d]pyrimidinone by a regiocontrolled bromination with NBS. The synthetic scaffolds were successfully converted into triazoles by copper(I)-catalyzed [3+2] cycloaddition and substituted at the 6-position by Suzuki-Miyaura cross-coupling in high overall yields. A microwave-assisted one-pot sequential synthesis involving esterification, formylation, bromination, and cyclization of anthranilic and 2-aminonicotinic acid derivatives provides access to N3-propargylquinazolinones or -pyridopyrimidinones in high overall yields. Functionalization by [3+2] cycloaddition and Suzuki-Miyaura cross-coupling rapidly led to 48 novel polyaromatic heterocycles.

Novel 3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines and its use

The present invention relates to novel 3 - ((1- benzyl - 1111.1 , 2, 3- triazole -4 - yl) methyl) quinazol -4 (3H) - won and N - (1- benzylpiperi -4 - yl) quinazoline -4 - amine and the use thereof. The present invention is more specifically described below. [AChE] The invention relates to novel Acetylcholine esterase ((3 - benzyl - 1111.1, 1- triazole 2,3- yl) methyl) quinazolin -4 - (3H) -4 and - won (N - benzylpiperi 1- yl) -4 - quinazoline -4 - amine and their use as therapeutic agents for neurological disorders.

Visible-light induced copper(i)-catalyzed oxidative cyclization of: O -aminobenzamides with methanol and ethanol via HAT

The use of the in situ generated ligand-copper superoxo complex absorbing light energy to activate the alpha C(sp3)-H of MeOH and EtOH via the hydrogen atom transfer (HAT) process for the synthesis of quinazolinones by oxidative cyclization of alcohols with o-aminobenzamide has been investigated. The synthetic utility of this protocol offers an efficient synthesis of a quinazolinone intermediate for erlotinb (anti-cancer agent) and 30 examples were reported.

Design, Synthesis and Bioevaluation of Two Series of 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines

Two series of 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines were designed initially as potential acetylcholine esterase inhibitors. Biological evaluation demonstrated that N-(1-benzylpiperidin-4-yl)quinazolin-4-amines significantly inhibited AChE activity. Especially, two compounds of them were found to be the most potent with relative AChE inhibition percentages of 87 percent in comparison to donepezil. The docking studies with AChE showed similar interactions between donepezil and four derivatives. N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines also exhibited significant DPPH scavenging effects. The two series of compound also exerted moderate to good cytotoxicity against three human cancer cell lines, including SW620 (human colon cancer), PC-3 (prostate cancer), and NCI?H23 (lung cancer), with 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one being the most cytotoxic agent. 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one significantly induced early apoptosis and arrested the SW620 cells at G2/M phase. From this study, two compounds of N-(1-benzylpiperidin-4-yl)quinazolin-4-amines could serve as new leads for further design and AChE inhibitors, while 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one could serve as a new lead for the design and development of more potent anticancer agents.

Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones

A selective functionalization of C-C-C bonds toward N-C-O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.

Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides

A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is

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.

Synthesis of new 1,2,3-triazol-4-yl-quinazoline nucleoside and acyclonucleoside analogues

In this study, we describe the synthesis of 1,4-disustituted-1,2,3- triazoloquinazoline ribonucleosides or acyclonucleosides by means of 1,3-dipolar cycloaddition between various O or N-Alkylated propargyl-quinazoline and 1'-Azido-2',3',5'-tri-Obenzoylribose or activated alkylating agents under microwave conditions. None of the compounds selected showed significant anti-HCV activity in vitro.

EXPANDED THERAPEUTIC POTENTIAL IN NITROHETEROARYL ANTIMICROBIALS

Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to imidazole, thiazole, and furan derivatives and their use as therapeutic agents.