13174-24-8

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL-(3,4-DIMETHOXY-BENZYL)-AMINE is used as a building block for the synthesis of various drugs and pharmaceuticals. Its unique structure and functional groups make it a valuable component in the development of new medications with potential therapeutic applications.
Used in Organic Synthesis:
BENZYL-(3,4-DIMETHOXY-BENZYL)-AMINE is used as a key intermediate in the synthesis of complex organic molecules. Its versatile structure allows for further functionalization and modification, enabling the creation of a wide range of organic compounds with diverse properties and applications.

InChI:InChI=1/C16H19NO2/c1-18-15-9-8-14(10-16(15)19-2)12-17-11-13-6-4-3-5-7-13/h3-10,17H,11-12H2,1-2H3

Upstream product

• 33859-00-6 benzyl-veratryliden-amine 
• 33859-00-6 N-benzyl-(3,4-dimethoxyphenyl)methanimine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 94271-49-5 diethyl N-benzyl-N-(3,4-dimethoxybenzyl)aminomalonate 
• 206125-93-1 2-[Benzyl-(3,4-dimethoxy-benzyl)-amino]-1-(4-methoxy-phenyl)-ethanone 
• 774539-01-4 2,6-dichloro-4,8-di-(N-benzyl-N-3',4'-dimethoxybenzylamino)pyrimido[5,4-d]pyrimidine 
• 94271-44-0 1-(3,4-Dimethoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid ethyl ester 
• 94271-46-2 1-(3,4-Dimethoxy-benzyl)-4-oxo-azetidine-2,2-dicarboxylic acid diethyl ester 
• 94271-50-8 2-[(2-Chloro-acetyl)-(3,4-dimethoxy-benzyl)-amino]-malonic acid diethyl ester 
• 94271-54-2 diethyl (3,4-dimethoxybenzylamino)malonate 
• 114041-14-4 2,3-Dihydro-5,6-dimethoxy-2-(phenylmethyl)-1H-isoindole 

Relevant academic research and scientific papers

Secondary amines: Synthesis and effect of length of spacer linking two phenyl rings on biological activity

N-Benzyl benzylamines (1a-11a) and N-benzyl anilines (1b-11b) were synthesized by sodium borohydride reduction of aldimines of benzylamine and aniline respectively. The products were characterized on the basis of elemental analysis and spectral studies and screened for antifungal potential against four fungi and evaluated for nematicidal activity against two nematodes. The former compounds were found to be more effective as compared to the latter thus indicating an enhancement of biological activity due to introduction of an extra methylene group between two phenyl rings of aromatic secondary amines.

Resistance-modifying agents. 11. Pyrimido[5,4-d]pyrimidine modulators of antitumor drug activity. Synthesis and structure-activity relationships for nucleoside transport inhibition and binding to α1-acid glycoprotein

The cardiovascular and antithrombotic agent dipyridamole (DP) has potential therapeutic utility as a modulator of the activity of antimetabolite antitumor agents by virtue of its inhibition of nucleoside transport. However, the activity of DP can be compromised by binding to the acute phase serum protein, α1-acid glycoprotein (AGP). Analogues of DP were synthesized and evaluated as inhibitors of 3H-thymidine uptake into L1210 leukamia cells in the presence and absence of 5 mg/mL AGP. Compounds with potency similar to that of DP were identified where the piperidino substituents at the 4,8-positions were replaced by 4?-methoxybenzylamino, 3?,4?-dimethoxybenzylamino, or piperonylamino groups. Replacement of the diethanolamino groups at the 2,6-positions of DP by alkylamino or alkoxy substituents was tolerated, although at least one oxygen-bearing function (hydroxyl or alkoxy) was required in the side chain for activity comparable to that of DP. Whereas AGP completely ablated the activity of DP, the majority of the newer compounds synthesized retained significant activity in the presence of excess AGP, although replacement of the piperidino groups at the 4,8-positions by N-methylbenzylamino substituents did, in some cases, restore susceptibility to AGP. Selected compounds have been demonstrated to prevent rescue from antifolate cytotoxicity, mediated by nucleoside salvage.

Simple synthetic equivalents for the β-(N,N-disubstituted)ethylamino acyl cation synthon and their applications

Various N,N-disubstituted-β-amino-N-methoxy-N-methylpropanamides 3a-i were prepared which served as an excellent β-aminoacyl cation equivalents. These were used to prepare β-amino ketones 1, pharmacologically active tertiary 1-(3,3-diarylpropyl)amines 7a-c, and the interesting C-glycoside 8.

Resistance-modifying agents. Part 7: 2,6-Disubstituted-4,8-dibenzylaminopyrimido[5,4-d]pyrimidines that inhibit nucleoside transport in the presence of α1-acid glycoprotein (AGP)

The synthesis and biological evaluation of potent 4,8-dibenzylaminopyrimidopyrimidine nucleoside transport inhibitors, with reduced binding to α1-acid glycoprotein, is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis of 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines via N,N-dibenzylphenacylamines

N,N-DibenzyIphenacylamines (1) were prepared in high yields by a onepot reaction and cyclized at room temperature to give 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cyclization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (If) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However la gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid at room temperature.