15775-59-4

Basic information

• Product Name: N¹-hydroxy-N³-phenylmalonamide
• CAS NO: 15775-59-4
• Molecular Weight: 194.19
• Mol File: 15775-59-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N¹-hydroxy-N³-phenylmalonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N¹-hydroxy-N³-phenylmalonamide(15775-59-4)
• EPA Substance Registry System: N¹-hydroxy-N³-phenylmalonamide(15775-59-4)

Safety Data

• Hazardous Substances Data: 15775-59-4(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 76311-94-9 Methyl 2-(N-phenylaminocarbonyl)acetate 

Relevant articles and documents

Phosphonate as a Stable Zinc-Binding Group for “Pathoblocker” Inhibitors of Clostridial Collagenase H (ColH)

Microbial infections are a significant threat to public health, and resistance is on the rise, so new antibiotics with novel modes of action are urgently needed. The extracellular zinc metalloprotease collagenase H (ColH) from Clostridium histolyticum is a virulence factor that catalyses tissue damage, leading to improved host invasion and colonisation. Besides the major role of ColH in pathogenicity, its extracellular localisation makes it a highly attractive target for the development of new antivirulence agents. Previously, we had found that a highly selective and potent thiol prodrug (with a hydrolytically cleavable thiocarbamate unit) provided efficient ColH inhibition. We now report the synthesis and biological evaluation of a range of zinc-binding group (ZBG) variants of this thiol-derived inhibitor, with the mercapto unit being replaced by other zinc ligands. Among these, an analogue with a phosphonate motif as ZBG showed promising activity against ColH, an improved selectivity profile, and significantly higher stability than the thiol reference compound, thus making it an attractive candidate for future drug development.