678536-02-2

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 613-94-5 benzoic acid hydrazide 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 1338091-90-9 (E)-N-benzyl-N'-(3,5-dimethoxybenzylidene)benzohydrazide 
• 1338091-89-6 (E)-N-allyl-N'-(3,5-dimethoxybenzylidene)benzohydrazide 
• 93014-11-0 2-(3,5-dimethoxyphenyl)-5-phenyl-1,3,4-oxadiazole 

Relevant academic research and scientific papers

An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent

Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.

Biological and quantitative-SAR evaluations, and docking studies of (E)-N′-benzylidenebenzohydrazide analogues as potential antibacterial agents

A series of 15 (E)-N′-benzylidenebenzohydrazide analogues were evaluated for their antimicrobial activities against eleven pathogenic and food-borne microbes, namely, S. aureus (G+), L. monocytogenes (G+), B. subtilis (G+), K. pneumonia (G-), C. sakazakii (G-), C. freundii (G-), S. enterica (G-), S. enteritidis (G-), E. coli (G-), Y. pestis (G-), and P. aeruginosa (G-). Most of the compounds exhibited selective activity against some Gramnegative bacterial strains. Of the compounds tested (3a-o), 3b and 3g were most active against C. freundii (MIC = ~19 μg mL-1). Whereas, compounds 3d, 3i, 3k and 3n exhibited MIC values ranging from 37.5 to 75 μg mL-1 against C. freundii, and compounds 3e, 3l and 3n had MIC values of ~75 μg mL-1 against K. pneumonia. Quantitative structure-antibacterial activity relationships were studied using physicochemical parameters and a good correlation was found between calculated octanol-water partition coefficients (clogP; a lipophilic parameter) and antibacterial activities. In silico screening was also performed by docking high (3b and 3g) and low (3n) activity compounds on the active site of E. coli FabH receptor, which is an important therapeutic target. The findings of these in silico screening studies provide a theoretical basis for the design and synthesis of novel benzylidenebenzohydrazide analogues that inhibit bacterial FabH.

Solvent-free synthesis of hydrazones and their subsequent N-alkylation in a Ball-mill

A large variety of Boc-, Bz-, Ts-, and Fmoc- protected hydrazones were prepared via condensation of an equimolar amount of carbonyl-compound and the corresponding hydrazine using a ball-mill. Hydrazones were always obtained in a quantitative yield and no solvents were used at any step. In a second step, we realized the first solvent-free N-allylation and N-benzylation of these hydrazones.