223401-28-3

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 371-40-4 4-fluoroaniline 
• 4114-31-2 ethylhydrazine carboxylate 
• 1195-45-5 para-fluorophenyl isocyanate 

Downstream Products

• 728919-69-5 4-(4-fluorophenyl)-1,2,4-triazolidine-3,5-dione 
• 219841-12-0 ethyl (4-fluorophenyl)aminocarbonyldiazenecarboxylate 

Relevant academic research and scientific papers

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

One-pot and novel route for the synthesis of 4-substituted-1,2,4- triazolidine-3,5-diones

The efficient and one-pot synthesis of 4-substituted-1,2,4-triazolidin-3,5- dione derivatives (4-substituted urazoles) via combination of triphosgene, substituted anilines, and ethyl carbazate in the presence of cesium carbonate is presented.

Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives

Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives were examined in a microplate assay at 50 μM for their ability to inhibit the growth of Leishmania donovani axenic amastigotes, a species that causes the fatal visceral leishmaniasis. GI50 (concentration for 50% growth inhibition) values of the most effective compounds were determined and their cytotoxicity on the human macrophage cell line THP-1 evaluated. The anti-leishmanial activity on L. donovani amastigotes growing in macrophages was also examined. The heterocycloadduct between 3,28-di-O-acetyllupa-12,18-diene and 4-methylurazine was the most effective derivative with an GI50 = 8.9 μM against L. donovani amastigotes.

Diazenedicarboxamides as inhibitors of d-alanine-d-alanine ligase (Ddl)

d-Alanine-d-alanine ligase (Ddl) catalyzes the biosynthesis of an essential bacterial peptidoglycan precursor d-alanyl-d-alanine and it represents an important target for development of new antibacterial drugs. A series of semicarbazides, aminocarbonyldiazenecarboxylates, diazenedicarboxamides, and hydrazinedicarboxamides was synthesized and screened for inhibition of DdlB from Escherichia coli. Compounds with good inhibitory activity were identified, enabling us to deduce initial structure-activity relationships. Thirteen diazenedicarboxamides were better inhibitors than d-cycloserine and some of them also possess antibacterial activity, which makes them a promising starting point for further development.