101421-72-1

Usage

Uses

Used in Pharmaceutical Industry:
6-Quinazolinamine (9CI) is used as a therapeutic target for the treatment of Huntington's disease. It has an effect on the TRPC1-mediated neuronal store-operated Ca entry pathway, which is crucial in delaying the progression of the disease's motor phenotype in Drosophila models. This makes it a promising compound for the development of new drugs and treatment strategies for Huntington's disease.
Additionally, 6-Quinazolinamine (9CI) can be used as a building block or intermediate in the synthesis of various quinazoline-based compounds with potential applications in the pharmaceutical industry, such as anticancer, antiviral, and anti-inflammatory agents. Its unique chemical properties allow for the development of novel drug candidates with improved efficacy and selectivity.

Synthesis Reference(s)

Tetrahedron, 62, p. 12351, 2006 DOI: 10.1016/j.tet.2006.09.103

InChI:InChI=1/C8H7N3/c9-7-1-2-8-6(3-7)4-10-5-11-8/h1-5H,9H2

Upstream product

• 19815-16-8 4-chloro-6-nitro-quinazoline 
• 7556-95-8 6-nitro-quinazoline 
• 67-56-1 methanol 
• 130130-88-0 6-azidoquinazoline 
• 109-86-4 2-methoxy-ethanol 
• 100-97-0 hexamethylenetetramine 
• 5466-93-3 diethyl 1,4-phenylenediamine-N,N'-dicarboxylate 
• 106-50-3 1,4-phenylenediamine 
• 253-82-7 quinazoline 

Downstream Products

• 645418-94-6 2-(quinazolin-6-ylamino)-benzoic acid ethyl ester 
• 124558-84-5 quinazolinylhydrazone de la cyclohexanedione-1,2 
• 700-78-7 6-chloroquinazoline 

Relevant academic research and scientific papers

6,6-Fused heterocyclic ureas as highly potent TRPV1 antagonists

A series of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N′-(6,6-fused heterocyclic) ureas have been investigated as hTRPV1 antagonists. Among them, compound 15 showed highly potent TRPV1 antagonism to capsaicin, with Ki(ant) = 0.2 nM, as well as antagonism to other activators, and it was efficacious in a pain model. A docking study of 15 with our hTRPV1 homology model indicates that there is crucial hydrogen bonding between the ring nitrogen and the receptor, contributing to its potency.

A microwave improvement in the synthesis of the quinazoline scaffold

A rapid and efficient microwave-assisted protocol is described that greatly improves a recent synthetic method developed for quinazoline synthesis. The synthetic protocol is based on the use of cycles of microwave irradiation. The optimization process is reported and the experimental results are compared with those of the conventional synthetic route.

A new access to quinazolines from simple anilines

A new synthetic pathway to quinazolines is described. This new method uses hexamethylenetetramine in TFA and potassium ferricyanide in aqueous ethanolic KOH, starting from simple N-protected anilines. The method affords substituted quinazolines with high

Pyrazole compounds

Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

PHOTOLYTIC RING-EXPANSIONS OF 4-AZIDOQUINOLINES AND 6-AZIDODIAZINES: SOME UNEXPECTED AZEPINE RING-OPENING REACTIONS

Photolysis of 6-azidoquinazoline in MeOH-KOMe-dioxan yields 8,9-dihydro-5,7-dimethoxy-5H-pyrimidoazepine (5) which on acid hydrolysis ring-opens to the pyrimidine-carbaldehyde (7).The mechanism of formation of this unexpected dimethoxypyrimido-azepine is discussed and related to previous similar results involving 6-azido-2,3-dihydrofuro- and 6-azido-2,3-dihydrothienoquinolines. In contrast, 6-azidoquinoxaline and 6-azido-2-chloro-4-methylquinoline on photolysis under similar conditions undergo ring expansion to the expected pyrazino- and pyridoazepines (22a) and (17) respectively.However, photolysis of the latter azide in MeOH-dioxan yields the 3-(2-pyridyl)propenonitrile derivative (18) in a reaction analogous to that undergone by 6-azidophenazine.