3556-83-0

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-METHOXY-4-METHYLBENZOATE is used as a reactant for the preparation of antimalaria drugs, specifically those that consist of the 4-aminoquinoline pharmacophore of chloroquine combined with clotrimazole-based antimalarials. Its unique chemical properties contribute to the development of effective treatments against malaria, a disease that affects millions of people worldwide.

Preparation

Methyl 3-methoxy-4-methylbenzoate is synthesized by the following steps:A mixture of methyl 3-hydroxy-4-methylbenzoate 36 (25 g, 0.151 mol), ?Me2SO4 (28.3 ml, 0.386 mol), anhydrous K2CO3 (103.5 g, 0.75 mol) was ?refluxed in acetone for 2 hours. K2CO3 was filtered off, washed ?thoroughly with acetone. The filtrates were combined and concentrated, ?the residue was redissolved in EtOAc washed with water, dried ?(anhydrous Na2SO4), filtered and concentrated in vacuo to furnish a white solid (19.52 g). ?Yield : 72%.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 33, p. 1771, 1990 DOI: 10.1021/jm00168a036

InChI:InChI=1/C10H12O3/c1-7-6-8(10(11)13-3)4-5-9(7)12-2/h4-6H,1-3H3

Upstream product

• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 7151-68-0 3-methoxy-p-toluic acid 
• 67-56-1 methanol 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 104901-43-1 methyl 3-bromo-4-methylbenzoate 
• 584-08-7 potassium carbonate 
• 121-44-8 triethylamine 
• 144-55-8 sodium hydrogencarbonate 
• 75-36-5 acetyl chloride 
• 62454-72-2 4-methyl-3-sulfobenzoic acid 
• 7697-26-9 3-bromo-4-methylbenzoic acid 

Downstream Products

• 7151-68-0 3-methoxy-p-toluic acid 
• 86239-03-4 ethyl 3-methoxy-4-methylbenzoate 
• 4685-50-1 3-methoxy-4-methylbenzyl alcohol 
• 70264-94-7 methyl 4-(bromomethyl)-3-methoxybenzoate 
• 193964-75-9 methyl 3-Methoxy-4-[(1-pyrrolidinyl)methyl]benzoate 
• 4685-51-2 4-(chloromethyl)-2-methoxy-1-methylbenzene 
• 140462-31-3 (+/-)-faveline methyl ether 
• 79236-96-7 2-methoxy-4-(hydroxymethyl)-3-methoxybenzoate 
• 74733-24-7 4-formyl-3-methoxybenzoic acid methyl ester 
• 188244-57-7 5-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-51-1 6-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-60-2 7-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-67-9 7-amino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 195433-20-6 7-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-3-methyl-4-oxo-1,4-dihydroquinoline 

Relevant academic research and scientific papers

Boosting Anti-Inflammatory Potency of Zafirlukast by Designed Polypharmacology

Multitarget design offers access to bioactive small molecules with potentially superior efficacy and safety. Particularly multifactorial chronic inflammatory diseases demand multiple pharmacological interventions for stable treatment. By minor structural changes, we have developed a close analogue of the cysteinyl-leukotriene receptor antagonist zafirlukast that simultaneously inhibits soluble epoxide hydrolase and activates peroxisome proliferator-activated receptor γ. The triple modulator exhibits robust anti-inflammatory activity in vivo and highlights the therapeutic potential of designed multitarget agents.

CHROMONE INHIBITORS OF S-NITROSOGLUTATHIONE REDUCTASE

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

SUBSTITUTED INDOLES

Disclosed herein are substituted indole cysteinyl leukotriene receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

An improved and scalable process for zafirlukast: An asthma drug

An improved and scalable process for the large-scale production of zafirlukast (Accolate), an important drug for asthma, is discussed along with impurity and scale-up-related issues.

PROCESSES FOR PREPARING ZAFIRLUKAST

An improved process for the preparation of substantially pure zafirlukast and pharmaceutical compositions thereof.

Antileishmanial activity screening of 5-nitro-2-heterocyclic benzylidene hydrazides

A series of 53 nitro derivatives rationally designed were obtained by parallel synthesis and screened against Leishmania donovani. Six compounds exhibited IC50 values lower than standard drugs. Brief SAR analysis revealed that substitution is important to the activity. Nitrothiophene analogues were more potent than the nitrofuran ones. This was attributed to the ability of sulfur atoms in accommodating electrons from nitro group, which facilitate its reduction and therefore the formation of free radicals lethal to parasites.

Stereoselective syntheses of (±)-komaroviquinone and (±)-faveline methyl ether through intramolecular Heck reaction

An efficient, flexible, and stereoselective convergent route for constructing the trans-10-hydroxy-1,1-dimethyloctahydrodibenzo[a,d]cyclohepten- 7-ones (5a-c) was achieved via intramolecular Heck reaction. This strategy has been successfully implemented for the syntheses of (±)-komaroviquinone (3) through (±)-coulterone dimethyl ether (5c) and (±)-faveline methyl ether (1a).

Oxidant scavengers

The present invention relates, in general, to a method of modulating physiological and pathological processes and, in particular, to a method of modulating intra- and extracellular levels of oxidants and thereby processes in which such oxidants are a participant. The invention also relates to compounds and compositions suitable for use in such methods.

CONDENSED PYRAZOLE DERIVATIVES, METHOD OF MANUFACTURING THE SAME, AND ANDROGEN INHIBITOR

This invention provides a condensed pyrazole derivative of the Formula (1): STR1 (where A denotes CH or N, R 0 and R 3 denote same or different, a hydrogen atom or a lower alkyl group, R 1 and R 2 denote same or different, a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a nitro group or a halogen atom, m denotes 1 or 2, and n denotes 1, 2 or 3, provided that, when n is 2, two R 2 may be connected to each other to form a lower alkylenedioxy group), or its pharmaceutically acceptable salt. This derivative or its salt is excellent in the effect of inhibiting the expression of action of androgen, thereby being excellent in therapeutical effect of benign prostatic hypertrophy, prostatic carcinoma, etc., and has a long lasting of efficacy and high oral absorption.

Process for the preparation of aromatic methyl methoxycarboxylates

The invention relates to a preparation process for aromatic methyl methoxycarboxylates by reaction of aromatic hydroxycarboxylic acids in the form of a mixture with the methoxycarboxylic acids with dimethyl sulphate in water.