612501-52-7

Basic information

• Product Name: 4-(3-Chloro-2-fluoroanilino)-6-hydroxy-7- methoxyquinazoline
• Synonyms: 4-(3-Chloro-2-fluoroanilino)-6-hydroxy-7- methoxyquinazoline;4-(3-chloro-2-fluorophenylamino)-7-methoxyquinazolin-6-ol
• CAS NO: 612501-52-7
• Molecular Formula: C₁₅H₁₁ClFN₃O₂
• Molecular Weight: 319.7181432
• EINECS: -0
• Mol File: 612501-52-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 458.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.489±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.17±0.40(Predicted)
• CAS DataBase Reference: 4-(3-Chloro-2-fluoroanilino)-6-hydroxy-7- methoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Chloro-2-fluoroanilino)-6-hydroxy-7- methoxyquinazoline(612501-52-7)
• EPA Substance Registry System: 4-(3-Chloro-2-fluoroanilino)-6-hydroxy-7- methoxyquinazoline(612501-52-7)

Safety Data

• Hazardous Substances Data: 612501-52-7(Hazardous Substances Data)

Usage

Appearance

4-(3-Chloro-2-fluoroanilino)-6-hydroxy-7- methoxyquinazoline is a light yellow to yellow powder or crystals.

Uses

Applications 4-((3-Chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol is a useful research chemical,it can be used as pharmaceutical intermediates.

Upstream product

• 2106-04-9 3-chloro-2-fluoroaniline 
• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 179688-52-9 6-hydroxy-7-methoxyquinazolin-4(3H)-one 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 20323-74-4 2-carboethoxy-4,5-dimethoxyaniline 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 100905-33-7 ethyl 2-nitro-4,5-dimethoxybenzoate 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 31839-21-1 2-amino-5-hydroxy-4-methoxybenzoic acid 
• 31839-20-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 740081-22-5 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate 
• 612501-80-1 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate monohydrochloride 

Downstream Products

• 612501-71-0 4-(3-chloro-2-fluoroanilino)-6-[(2S,4R)-1-(t-butoxycarbonyl)-2-(methoxycarbonyl)pyrrolidin-4-yloxy]-7-methoxyquinazoline 
• 848440-15-3 4-(3-chloro-2-fluoroanilino)-6,7-dihydroxyquinazoline 
• 612501-81-2 tert-butyl 4-((4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)piperidine-1-carboxylate 
• 1046137-43-2 4-[(3-chloro-2-fluoro-phenyl)amino]-6-(1,4-dioxa-spiro[4.5]decan-8-yl-oxy)-7-methoxy-quinazoline 
• 1178976-85-6 Methyl trans-1-tert.-butoxycarbonylamino-4-[4-(3-chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanecarboxylate 
• 1441145-46-5 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(N-methylcarbamoylethyl)piperidin-4-yl]oxy}quinazoline 
• 1441145-65-8 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(N-methylcarbamoylmethyl)azetidin-3-yl]oxy}quinazoline 
• 848942-61-0 Sapitinib 
• 612500-78-4 N-(3-chloro-2-fluorophenyl)-7-methoxy-6-(piperidin-4-yloxy)quinazolin-4-amine 
• 1441146-12-8 tert-butyl [4-({4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl}oxy)piperidin-1-yl]propionate 
• 1441146-99-1 6-(azetidin-3-yloxy)-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline 
• 1441145-10-3 4-(3-chloro-2-fluoroanilino)-6-{[1-(N-isopropylcarbamoylmethyl)piperidin-4-yl]oxy}-7-methoxyquinazoline 
• 848942-78-9 4-(3-chloro-2-fluoroanilino)-6-{[1-(N,N-dimethylcarbamoylmethyl)piperidin-4-yl]oxy}-7-methoxyquinazoline 

Relevant articles and documents

Design, synthesis and biological evaluation of sulfamoylphenyl-quinazoline derivatives as potential EGFR/CAIX dual inhibitors

Multi-target, especially dual-target, drug design has become a popular research field for cancer treatment. Development of small molecule dual-target inhibitors through hybridization strategy can provide highly potent and selective anticancer agents. In this study, three series of quinazoline derivatives bearing a benzene-sulfonamide moiety were designed and synthesized as dual EGFR/CAIX inhibitors. All the synthesized compounds were evaluated against epidermoid carcinoma (A431) and non-small cell lung cancer (A549 and H1975) cell lines, which displayed weak to potent anticancer activity. In particular, compound 8v emerged as the most potent derivative against mutant-type H1975 cells, which exhibited comparable activity to osimertinib. Importantly, 8v exhibited stronger anti-proliferative activity than osimertinib against H1975 cells under hypoxic condition. Kinase inhibition studies indicated that 8v showed excellent inhibitory effect on EGFRT790M enzyme, which was 41 times more effective than gefitinib and almost equal to osimertinib. Mechanism studies revealed that 8v exhibited remarkable CAIX inhibitory effect comparable to acetazolamide and significantly inhibited the expression of p-EGFR as well as its downstream p-AKT and p-ERK in H1975 cells. Notably, 8v was found to inhibit the expression of CAIX and its upstream HIF-1α in H1975 cells under hypoxic condition. Molecular docking was also performed to gain insights into the ligand-binding interactions of 8v inside EGFRWT, EGFRT790M and CAIX binding sites.

Polysubstituted quinazoline compound and application thereof

The invention discloses a polysubstituted quinazoline compound and an application thereof, and belongs to the field of chemical medicines. The substituted quinazoline compound represented by the general formula (I) and the pharmaceutically acceptable salt thereof have excellent brain barrier permeability, enhanced metabolic stability and longer metabolic half-life period, show higher inhibitory activity on an activated or drug-resistant mutant form EGFR than a wild type EGFR, and can effectively reduce side effects.

Novel method of synthetic process of lung cancer targeted compound AZD-3759

The invention discloses a novel method of a synthetic process of a lung cancer targeted compound AZD-3759. The novel method comprises the following specific steps: carrying out chlorination on 3,4-dihydro-7-methoxyl-4-oxyquinazoline-6-farnesyl acetate to obtain a compound 2; reacting the compound 2, a compound 3 and an organic solvent to obtain a compound 4, and carrying out hydrolysis reaction toobtain a compound 5; reacting a compound 6, dichloromethane and Boc-anhydride to obtain a compound 7; reacting the compound 7 and pyridine with triphosgene by taking dichloromethane as a solvent to obtain a compound 8; and reacting the compound 5, the compound 8, organic alkali and DMF to obtain a compound 9, desorbing Boc from an acidic system, regulating pH to obtain a compound 10, carrying outmethylation, adjusting pH and separating out, and refining to obtain AZD-3759. The novel method of the synthetic process of the lung cancer targeted compound AZD-3759 has the beneficial effects thatthe raw materials for the novel method are easily obtained, the price is low, the yield is high, the cost is low, the method is environmentally friendly, and industrialized enlarged production can berealized.