162012-72-8

Usage

Uses

Used in Pharmaceutical Industry:
6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE is used as a potential 2-arylbenzothiazoles based kinase inhibitor for its ability to modulate cellular signaling pathways involved in various diseases, including cancer. Its kinase inhibitory activity makes it a promising candidate for the development of targeted therapeutics against specific types of cancer.
Used in Drug Discovery and Development:
In the field of drug discovery and development, 6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE serves as a valuable chemical scaffold for the design and synthesis of novel inhibitors targeting various kinases. Its unique structure allows for further optimization and modification to enhance its potency, selectivity, and pharmacokinetic properties, ultimately leading to the development of more effective and safer drugs.
Used in Research and Development of Kinase Inhibitors:
6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE is utilized as a starting point for the research and development of new kinase inhibitors. Its structure can be modified and optimized to improve its binding affinity, selectivity, and efficacy against specific kinase targets. 6-METHOXY-7-HYDROXYQUINAZOLIN-4-ONE plays a crucial role in advancing our understanding of kinase biology and the development of targeted therapies for various diseases, including cancer.

Upstream product

• 179688-01-8 7-(benzyloxy)-6-methoxyquinazolin-4(3H)-one 
• 848092-84-2 methyl 2-amino-4-hydroxy-5-methoxybenzoate 
• 77287-34-4 formamide 
• 16712-16-6 ammonium formate 
• 741276-49-3 C₁₆H₁₄N₂O₂ 
• 916606-81-0 7-hydroxy-6-methoxyquinazoline 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 56441-97-5 methyl 4-(benzyloxy)-3-methoxybenzoate 
• 61032-41-5 methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate 
• 61032-42-6 methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate 

Downstream Products

• 179688-02-9 7-acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one 
• 1622396-50-2 C₃₂H₃₈N₆O₅ 
• 1622396-69-3 C₂₁H₂₂ClN₃O₅ 
• 1622396-70-6 C₂₆H₂₆ClN₅O₇ 
• 1622396-71-7 C₂₄H₂₂ClN₅O₇ 
• 1622343-29-6 C₃₁H₃₃ClN₆O₇ 
• 1622396-72-8 C₂₉H₂₈ClFN₄O₆ 
• 1622396-73-9 C₂₇H₂₄ClFN₄O₆ 
• 1622343-45-6 C₃₄H₃₅ClFN₅O₆ 
• 1622396-81-9 C₂₁H₂₂ClN₃O₅ 
• 1622343-33-2 C₂₉H₂₈ClFN₄O₆ 
• 1622343-17-2 C₂₆H₂₆ClN₅O₇ 
• 263400-68-6 4-chloro-6-methoxy-quinazolin-7-ol 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 

Relevant academic research and scientific papers

Gefitinib and its derivatives of the new method for microwave synthesis

The invention discloses a new method for performing microwave synthesis on gefitinib and a derivative thereof. The method comprises the following steps of: at first, synthesizing 6-methoxyl-7-hydroxyl quinazoline-4-one from 2-iodo (bromo)-4-methoxyl-5-hydroxyl cyanophenyl used as an initial raw material and formamidine hydrochloride in a microwave mode; then performing reaction with 4-(3-bromo propyl) morpholine to introduce an alkyl side chain so as to obtain 7-methoxyl-6-[3-(4-morpholinyl) propoxy] quinazoline-4-ketone; in the presence of a catalyst, performing reaction on the obtained product and a chlorination reagent to obtain 4-chloro-7-methoxyl-6-[3-(4-morpholinyl) propoxy] quinazoline; finally, performing reaction on 4-chloro-7-methoxyl-6-[3-(4-morpholinyl) propoxy] quinazoline and 3-chloro-4-fluoroaniline to obtain a final product 4-(3-chloro-4-fluoroanilino)-7-methoxyl-6-(3-morpholinyl propoxy) quinazoline (gefitinib). The whole route steps are simplified into four steps, the yield is high, the method is convenient to carry out, the dangerousness is low, and the application of high-pollution reagents is reduced; moreover, the whole route is high in economy and suitable for industrial production, and the product cost is reduced. The reaction formula is as shown in the specification.

THERAPEUTIC COMPOUNDS AND USES THEREOF

Described herein are compounds of Formula (I) or Formula (VI), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Also provided are particles (e.g., nanoparticles) comprising compounds of Formula (I) or Formula (VI) and pharmaceutical compositions thereof that are mucus penetrating. Methods of using the compounds or pharmaceutical compositions thereof for treating diseases are also provided.

Identification of novel 4-anilinoquinazoline derivatives as potent EGFR inhibitors both under normoxia and hypoxia

A novel series of 4-anilinoquinazoline derivatives (19a-19t) were designed and synthesized through incorporation of the 2-nitroimidazole moiety into the 4-anilinoquinazoline scaffold of EGFR inhibitors. The most promising compound 19h displayed potent EGF

Facile and efficient oxidation of quinazolines into quinazolin-4(3 H)-ones by peracetic acid

A new approach to synthesize quinazoline-4(3H)-ones was achieved by oxidation of quinazolines using peracetic acid, which possesses some advantages of economic reagents, simplified operation, high efficiency, and environmental friendliness. Application of this method allowed us to synthesize a series of quinazolin-4(3H)-ones with different substituents at 6 and 7 positions in good to excellent yields, including the key intermediates of tyrosine kinase inhibitors such as PD153035, Erlotinib, and Gefitinib. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Substituted 2-arylbenzothiazoles as kinase inhibitors: Hit-to-lead optimization

Based on an (aminoaryl)benzothiazole quinazoline hit structure for kinase inhibition, a systematic optimization program resulted in a lead structure allowing for inhibitory activities in cellular phosphorylation assays in the low nanomolar range.

Thiazole Analogues and Uses Thereof

Compounds of formula (I) and salts and physiologically functional derivatives thereof, wherein R2 is attached at the 4- or 5-position of the thiazole ring and is hydrogen, alkyl, halogen, cyano, alkoxy, haloalkoxy, or alkylamino; X independently represents a divalent linkage group selected from S, O, NR4, SO, or SO2; R4 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, or heterocyclyl; R1 is attached at the 4- or 5-position of the thiazole ring and independently represents a group of formula (II): ?wherein the dotted line represents a single or double bond; * indicates the point of attachment to the thiazole ring; and n is 1, 2, or 3. Also disclosed are pharmaceutical compositions comprising the above compounds and method of treatments for cancer and other diseases.

2-arylbenzothiazole analogues and uses thereof

The present invention relates to compounds of the general formula (I) and salts, prodrugs, and stereoisomers thereof, wherein Y independently represents S, O, NR2, SO, SO2; A independently represents a fife- or six-membered aromatic carbocycle or heterocycle and wherein R1 to R20 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties.

Thiazole analogues and uses thereof

The present invention relates to compounds of the general formula (I) and salts and physiologically functional derivatives thereof, R2 is attached at the 4- or 5-position of the thiazole ring and is hydrogen, alkyl, halogen, cyano, alkoxy, haloalkyloxy, or alkylamino; X independently represents a divalent linkage group selected from S, O, NR4, SO, or SO2; R4 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, or heterocyclyl; is attached at the 4- or 5-position of the thiazole ring and independently represents one of the following groups of the general formula (II): wherein the dotted line represents a single or double bond; * indicates the point of attachment to the thiazole ring; n is 1,2, or 3.

2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer

The present invention relates to anticancer compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein Y independently represents S, O, NR 2 , SO, SO 2 ; A independently represents a five- or six-membered aromatic carbocycle or heterocycle and wherein R 1 in formula (I) represents one of the heteroaryl groups defined in the claims.

2,5- and 2,6-disubstituted benzazole derivatives useful as protein kinase inhibitors

The present invention relates to compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein the substituent is attached to the 5- or 6- position of the benzazole; Xindependently represents S, O, SO, SO2;Yindependently represents S, O, NR2, SO, SO2;Aindependently represents ←CO-, ←CS-, ←SO-, ←SO2-, ←CO2-, ←CONR8-, ←NR8CO-, ←NR8CONR9-, ←NR8COO-, ←NR8NR9CO-, ←NR8OCO-, ←ONR8CO-, ←NR8SO2-, where ← indicates the point of attachment to R3; and wherein R1 to R19 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties. These compounds are useful as protein kinase inhibitors in the treatment of i.a. cancer.