80648-69-7

Upstream product

• 94-08-6 4-methylbenzoic acid ethyl ester 
• 107-15-3 ethylenediamine 
• 99-94-5 p-Toluic acid 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 22404-86-0 N,N'-methylenebis(4-methylbenzamide) 
• 104-85-8 para-methylbenzonitrile 
• 619-55-6 para-methylbenzamide 

Relevant academic research and scientific papers

Synthesis, characterization, in vitro biological and molecular docking evaluation of N,N'-(ethane-1,2-diyl)bis(benzamides)

The present research describes the synthesis, characterization, in vitro biological and docking evaluation of N,N'-(ethane-1,2-diyl)bis(benzamides) (3a-3j). Consequently, in in vitro hRBCs hemolysis assay, only the bis-amide (3d) induced 52.4% hemolysis at higher concentration (1000?μg/mL) that decreased drastically with concentration (250?μg/mL) to 27.9% (CC50 = 400.41). Similarly, the tested bis-amide (3j) was found to be the least toxic with 7.8% hemolysis at higher concentration (1000?μg/mL) that gradually decreases to 6.1% (CC50 = 19,347.83) at lower concentration (250?μg/mL). Accordingly, the tested bis-amides were found to be highly biocompatible against hRBCs at higher concentrations with much higher CC50 values (> 1000?μg/mL). The biocompatible bis-amides (3a-3j) were subjected to in vitro DNA ladder assay to analyze their apoptotic potential. The results obtained suggest the tested bis-amides (3a-3j) are highly degradative toward DNA causing the appearance of more than one bands or complete degradation of DNA except (3a), (3c), (3i) and (3?g). Moreover, the synthesized bis-amides (3a-3j) were tested in in vitro antileishmanial assay to unveil their leishmaniacidal potential. The results obtained clearly indicated that some of the tested bis-amides displayed good dose dependent response. The tested bis-amides were highly active at higher concentration (1000?μg/mL) against the leishmanial promastigotes and their % inhibitory potential decreased drastically with concentration (250?μg/mL). Consequently, at higher concentration (1000?μg/mL), the bis-amide (3f) caused 85% inhibition and was ranked as the most effective leishmaniacidal bis-amides followed by the bis-amide (3?g) with 73.54% inhibition of leishmanial promastigotes. However, in terms of their IC50 values, the best leishmaniacidal potential was displayed by the bis-amide (3f) followed by (3b), (3j) and (3?g) with IC50 values increasing in the order of 633.16, 680.22, 680.22 and 712.93?μg/mL, respectively. Molecular docking studies revealed that bis-amides having electron-donating groups showed good binding potential against antileishmanial target. Graphic abstract: [Figure not available: see fulltext.].

One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).

N,N'-Doacylated imidazolidines and hexahydropyrimidines

A method for the preparation of N-monoacyl imidazolidines and hexahydropyrimidines (as hydrochlorides) by interaction of monoacylated derivatives of ethylenediamine and trimethylethylenediamine with chloromethyl methyl ether was developed.Also a method for the preparation of N,N'-diacylimidazolidines and hexahydropyrimidines either by acylation of their monoacyl derivatives or by reaction of the corresponding N,N'-diacyl alkylenediamine derivatives with dimethoxymethane, diacetoxymethane, 1,3,5-trioxane or chloromethyl methyl ether was designed. - Key words: N-mono- and N,N'-diacylated imidazolidines, N-mono- and N,N'-diacylated hexahydropyrimidines, N,N'-diacylated alkylenediamines, acylation, methylation, cyclization.

Structure-activity relationships of diamines, dicarboxamides, and disulfonamides on vinblastine accumulation in P388/ADR cells

Diamines, dicarboxamides, and disulfonamides that have terminal benzene, methyl- or chloro-substituted benzene rings were synthesized and evaluated for the activity of [3H]vinblastine accumulation in multidrug-resistant P388/ADR cells. The effi