214472-41-0

Basic information

• Product Name: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester
• Synonyms: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester;Methyl 2-aMino-4-Methoxy-3-(3-Morpholinopropoxy)benzoate;Methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate;Methyl 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzoate
• CAS NO: 214472-41-0
• Molecular Formula: C₁₆H₂₄N₂O₅
• Molecular Weight: 324.37216
• Mol File: 214472-41-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester(214472-41-0)
• EPA Substance Registry System: Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester(214472-41-0)

Safety Data

• Hazardous Substances Data: 214472-41-0(Hazardous Substances Data)

Usage

General Description

Benzoic acid, 2-amino-4-methoxy-5-[3-(4-morpholinyl)propoxy]-, methyl ester is a chemical compound that contains a benzoic acid core with a methoxy group at the 4-position and an amino group at the 2-position. Additionally, it also contains a morpholinyl group attached to a propoxy chain at the 5-position. Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester is commonly used in the pharmaceutical industry as it exhibits various pharmacological activities. It has been studied for its potential use in the treatment of various diseases, including cancer and neurodegenerative disorders. Additionally, it is used in research as a reference standard for analytical testing.

Upstream product

• 214472-37-4 4-methoxy-5-(3-morpholinylpropoxy)-2-nitrobenzoic acid methyl ester 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 380844-22-4 methyl 3-(3-chloropropoxy)-4-methoxybenzoate 
• 380844-24-6 methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate 
• 645-08-9 Isovanillic acid 
• 214472-17-0 4-methoxy-5-[3-(4-morpholinyl)propoxy]benzoic acid methyl ester 
• 215659-03-3 methyl 5-hydroxy-4-methoxy-2-nitrobenzoate 

Downstream Products

• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 184475-35-2 gefitinib 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 
• 252264-46-3 ethyl 2-(dimethylaminomethyleneamino)-4-methoxy-5-(3-morpholin-4-yl-propoxy)benzoate 
• 214486-62-1 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-7-methoxy-6-(3-morpholin-4-yl)-propoxyl-quinoline-3-carbonitrile 

Relevant articles and documents

Electroreduction preparation method of gefitinib intermediate

The invention discloses an electroreduction preparation method of a gefitinib intermediate. The electroreduction preparation method comprises the steps that an acidic aqueous solution of 4-methoxy-5-(3-morpholinylpropoxy)-2-nitrobenzoate is used as cathode liquor in a diaphragm electrolyzer; the acidic aqueous solution is used as anode liquor; and relative to a reference electrode, the voltage ofa cathode working electrode is 1.00V-2.50V, the current density of the cathode working electrode is 25.0 mA/cm-250.0 mA/cm, the working temperature of an electrolytic cell is between 25 DEG C-80DEG C, electrolysis is performed, and gefitinib intermediate 2-amino-4-methoxy-5-(3-morpholinylpropoxy)methyl benzoate is prepared. In the electroreduction process, a reducing agent or an organic solvent is not used, by changing the electrode potential, the conversion rate and selectivity can be controlled, and a high-purity and high-yield intermediate is obtained.

A new heterocyclic compound initiates ROS accumulation and cause apoptotic cell death in human bone cancer cells

A new heterocyclic compound 7-methoxy-6-(3-morpholinopropoxy)quinazolin-4(3H)-one (1), designed using methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (2) as the starting material, was successfully obtained via multiple synthesis route and finally characterized by fourier transform infrared (FT-IR) spectroscopy, 1H nuclear magnetic resonance (NMR), and single crystal X-ray crystallography. We investigated its effect on cell viability and proliferation with Cell Counting Kit-8 (CCK8) assay. The results revealed that compound 1 could block the proliferation of Saos-2 bone cancer cells. In addition, Annexin V-FITC/PI assay and Western blot analysis were performed to detect whether compound 1 could induce cell apoptosis. The results indicated that compound 1 could increase the number of apoptotic cells remarkably. Moreover, we examined the impact of compound 1 on ROS generation. Results revealed that compound 1 up-regulated the reactive oxygen species (ROS) genes expression and promoted the accumulation of ROS in Saos-2 cells. Finally, molecular docking has been utilized to study the binding mode of compound 1 with tubulin.

A PROCESS FOR THE PREPARATION OF GEFITINIB

The present invention provides an improved, industrial advantageous process for the preparation of gefitinib of formula (I), and its pharmaceutically acceptable salts thereof in high yield and purity.