18595-14-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-amino-3-methylbenzoate is used as a key intermediate in the synthesis of neuroprotective hydrazides. These hydrazides are essential in the treatment of Alzheimer's disease, a neurodegenerative condition that affects memory and cognitive function. The compound's role in creating these protective agents highlights its importance in developing therapies for Alzheimer's patients.
Additionally, Methyl 4-amino-3-methylbenzoate is used in the research and development of diphenylamine-based retinoids. Retinoids are a class of compounds derived from vitamin A, which play a crucial role in cell growth, differentiation, and vision. They are widely used in the treatment of various skin conditions, such as acne and psoriasis, as well as in anti-aging skincare products. The compound's involvement in the synthesis of these retinoids underscores its significance in the pharmaceutical and cosmetic industries.

InChI:InChI=1/C9H11NO2/c1-6-5-7(9(11)12-2)3-4-8(6)10/h3-5H,10H2,1-2H3

Upstream product

• 24078-21-5 methyl 3-methyl-4-nitrobenzoate 
• 67-56-1 methanol 
• 2486-70-6 4-amino 3-methylbenzoic acid 
• 186581-53-3 diazomethane 
• 3113-71-1 3-methyl-4-nitrobenzoic acid 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 301533-59-5 methyl 4-(n-butyrylamino)-3-methylbenzoate 
• 180624-11-7 methyl 4-amino-3-iodo-5-methyl-benzoate 
• 569344-32-7 methyl 4-amino-3-methyl-5-methylthiomethylbenzoate 
• 3095-48-5 4-amino-3,5-dimethyl-benzoic acid methyl ester 
• 948552-50-9 3,5-dimethyl-4-propionylamino-benzoic acid methyl ester 
• 167626-74-6 3,5-dimethyl-4-propionylaminobenzoic acid 
• 167626-17-7 1-(3,5-dimethyl-4-propionylamino)benzoyl-4-(N-methyl-2-phenylethyl)aminopiperidine 
• 152628-02-9 2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole 
• 144701-48-4 telmisatran 
• 144702-26-1 tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate 
• 88089-56-9 3-Methyl-4-(2-oxo-azetidin-1-yl)-benzoic acid 
• 88072-21-3 3-Methyl-4-(2-oxo-azetidin-1-yl)-benzoic acid methyl ester 
• 719300-00-2 3-Methyl-4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-benzoic Acid Methyl Ester 
• 864296-43-5 4-isocyanato-3-methyl-benzoic acid methyl ester 

Relevant academic research and scientific papers

Hysteretic carbon dioxide sorption in a novel copper(ii)-indazole- carboxylate porous coordination polymer

The synthesis, structural and gas sorption studies of a porous Cu(ii) coordination polymer featuring 1H-indazole-5-carboxylic acid (H2L) are presented. [Cu(HL)2] is a thermally and hydrolytically robust 4-connected 3D coordination polymer of NbO topology and is replete with 1D channels that permit selective and hysteretic sorption of CO2. The Royal Society of Chemistry 2012.

Laser-induced fluorescence and dispersed fluorescence studies of the donor-acceptor system 4-amino 3-methyl benzoic acid methyl ester and its solvated clusters: Evidence of excited-state charge-transfer reaction

Laser-induced fluorescence (LIF) excitation and dispersed fluorescence (DF) spectra of 4-amino 3-methyl benzoic acid methyl ester (AMBME) and its solvated clusters with solvents such as methanol, water and acetonitrile have been investigated in a supersonic expansion. Spectral signature supports the presence of two conformers in the cooled jet which is in line with theoretical calculations. In addition to structured local emission from the Franck Condon excited state, the molecule AMBME shows red-shifted broad emission from the state attributed to the close-lying charge transfer (CT) state, which is facilitated by exciting low-frequency modes. The molecule readily forms clusters with different solvents and the clusters' electronic excitation bands appear in the low-energy side of the transition origin of the bare molecule. Excitation of the clusters leads to the appearance of red-shifted solvent-polarity dependent CT emission.

Novel preparation method of antihypertensive drug telmisartan intermediate

The invention relates to an electric reduction preparation method of aminobenzoic acid represented by formula I and ester thereof. The preparation reaction of the method is shown in the description; and in the reaction formula, R is selected from hydrogen, a methyl group, an ethyl group, a benzyl group, a C3 or C4 straight-chain alkyl or branched-chain alkyl group, -NO2 is selected from 4-NO2 or 5-NO2, and Y is selected from H or 4-NHCOC3H7-n. The electroreduction preparation method of aminobenzoic acid and ester I thereof is characterized in that in a separated electrolytic cell, an acidic solution of nthe itrobenzoic acid and ester III thereof is taken as a catholyte; the voltage of a cathode working electrode relative to a reference electrode is 1.00-2.50 V; and an anolyte is an acidicsolution, the current density is 25.0-250.0 mA/cm, and the electrolysis temperature is 15-90 DEG C.

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

One-dimensional channels encapsulated in supramolecular networks constructed of zinc(II), manganese(II), or nickel(II) atoms with 3-(Carboxymethyl)-2, 7-dimethyl-3H-benzo[d]imidazole-5-carboxylic Acid

Four complexes with supramolecular architectures, namely, MZCA·3H2O (1), [Zn(H2O)6] 2+·[MZCA]2·[H2O]6 (2), [Mn(MZCA)2(H2O)4]·2H2O (3), and [Ni(MZCA)2(H2O)4]·2H2O (4) [MZCA = 3-(carboxymethyl)-2, 7-dimethyl-3H-benzo[d]imidazole-5-carboxylic acid], were synthesized and characterized by elemental analysis, IR spectroscopy, and single-crystal X-ray diffraction. Complexes 1 and 2 display a remarkable 3D network with 1D hydrophilic channels. Complexes 3 and 4 are isostructural and exhibit a 3D structure encapsulating 1D 24-membered ring microporous channels. The UV/Vis and fluorescent spectra were measured to characterize complexes 1-4. The thermal stability of complexes 2-4 were also examined.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

One-pot synthesis of novel 3,5-disubstituted-1,2,4-oxadiazoles from indazole carboxylic acid esters and amidoximes

An efficient and high-yielding one-pot synthesis of 3,5-disubstituted-1,2, 4-oxadiazoles from indazole carboxylic acid methyl esters and amidoximes is described. In this study a series of novel 3,5-disubstituted-1,2,4-oxadiazoles (3a-d), (4a-d), (5a-d), (6a-d), (7a-d) were synthesized using amidoximes 2a-d and indazole carboxylic acid esters (3-6).

Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel

In order to find novel and environmental friendly insecticides targeting the ryanodine receptor, three series of novel phthalamides containing heptafluoroisopropyl group, low fluorine atoms group and non-fluorine group were designed and synthesized. 35 novel structures of three series were obtained. Insecticidal activities of title compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of title compounds showed moderate to high activities at the tested concentration. The structure-activity relationship (SAR) was discussed in detail. During synthesizing title compounds B8, C7, D1, D9 and D12, their corresponding positional isomers (B8′, C7′, D1′, D9′ and D12′) were afforded, and their structures were confirmed by 2D NMR. The calcium-imaging technique was also applied to investigate the effects of compounds B2, B10, C4 and C5 on the intracellular calcium ion concentration ([Ca2+]i), which indicated that they released stored calcium ions from endoplasmic reticulum, which denoted that some compounds are potential modulators of the insect ryanodine receptor (RyR).

Structure-activity relationship study on benzoic acid part of diphenylamine-based retinoids

Based on structure-activity relationship studies of the benzoic acid part of diphenylamine-based retinoids, the potent RXR agonist 4 was derivatized to obtain retinoid agonists, synergists, and an antagonist. Cinnamic acid derivatives 5 and phenylpropionic acid derivatives 6 showed retinoid agonistic and synergistic activities, respectively. The difference of the activities is considered to be due to differences in the flexibility of the carboxylic acid-containing substituent on the diphenylamine skeleton. Compound 7, bearing a methyl group at the meta position to the carboxyl group, was an antagonist, dose-dependently inhibiting HL-60 cell differentiation induced by 3.3 × 10-10 M Am80.