64487-10-1

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 60-34-4 methylhydrazine 
• 3156-37-4 4-bromo-β-nitrostyrene 
• 20244-39-7 methyl hydrazine monohydrate 

Downstream Products

• 64643-25-0 (E)-3-{N'-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-N-methyl-hydrazino}-but-2-enoic acid ethyl ester 
• 1450908-55-0 (1S,5S)-4-(4-bromophenyl)-2-methyl-2,3-diazabicyclo[3.3.1]non-3-en-1-ol 
• 1450908-87-8 (E)-3-(2-(4-bromobenzylidene)-1-methylhydrazinyl)cyclohexanone 
• 1541191-29-0 N¹-2-(4-bromobenzylidene)-N⁴-(2,6-dimethylphenyl)-1-methylhydrazinecarboxamide 
• 69746-36-7 5-(4-bromophenyl)-2-methyl-2H-tetrazole 
• 73387-51-6 3-(4-bromophenyl)-1-methyl-1H-pyrazole 
• 135676-92-5 1,2,3,4-tetrahydro-1-methyl-3-(p-bromophenyl)-4-phenyl-6-acetyl-s-tetrazine 

Relevant academic research and scientific papers

Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process

In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.

Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene

A variety of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles were directly prepared in good to moderate yields by the reaction of aromatic aldehydes with methylhydrazine and benzylhydrazine, followed by treatment with di-tert-butyl azodicarboxylate and [bis(trifluoroacetoxy)iodo]benzene in a mixture of dichloromethane and 2,2,2-trifluoroethanol at room temperature. The present method is a novel one-pot preparation of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles through a [2N + 2N] combination under transition metal-free and mild conditions.

Structure-activity relationship of semicarbazone EGA furnishes photoaffinity inhibitors of anthrax toxin cellular entry

EGA, 1, prevents the entry of multiple viruses and bacterial toxins into mammalian cells by inhibiting vesicular trafficking. The cellular target of 1 is unknown, and a structure-activity relationship study was conducted in order to develop a strategy for target identification. A compound with midnanomolar potency was identified (2), and three photoaffinity labels were synthesized (3-5). For this series, the expected photochemistry of the phenyl azide moiety is a more important factor than the IC50 of the photoprobe in obtaining a successful photolabeling event. While 3 was the most effective reversible inhibitor of the series, it provided no protection to cells against anthrax lethal toxin (LT) following UV irradiation. Conversely, 5, which possessed weak bioactivity in the standard assay, conferred robust irreversible protection vs LT to cells upon UV photolysis.