219618-11-8

Basic information

• Product Name: N-(4-acetylphenyl)-2-cyanoacetamide
• Synonyms: N-(4-acetylphenyl)-2-cyanoacetamide;2-cyano-N-(4-ethanoylphenyl)ethanamide;IVK/9146688
• CAS NO: 219618-11-8
• Molecular Formula: C₁₁H₁₀N₂O₂
• Molecular Weight: 202.2093
• Mol File: 219618-11-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-acetylphenyl)-2-cyanoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-acetylphenyl)-2-cyanoacetamide(219618-11-8)
• EPA Substance Registry System: N-(4-acetylphenyl)-2-cyanoacetamide(219618-11-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 219618-11-8(Hazardous Substances Data)

Upstream product

• 99-92-3 p-aminobenzophenone 
• 372-09-8 cyanoacetic acid 
• 16130-58-8 cyanoacetic acid chloride 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 

Downstream Products

• 136186-31-7 (Z)-N-(4-Acetyl-phenyl)-2-cyano-3-hydroxy-3-(4-trifluoromethyl-phenyl)-acrylamide 
• 1430721-82-6 1-(4-acetylphenyl)-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 

Relevant articles and documents

3-(3,5-Dimethyl-1H-Pyrazol-1-yl)-3-Oxopropanenitrile as Precursor for Some New Mono-Heterocyclic and Bis-Heterocyclic Compounds

3-(3,5-Dimethyl-1 H -pyrazol-1-yl)-3-oxopropanenitrile 1 was used as a cyanoacetylating agent for synthesis of the acetanilide derivative 3. Compound 3 was utilized as a key intermediate for the synthesis of some new mono-chromene and di-chromene derivatives 9 and 13, the dihydrazo derivatives 15, and the dithiazole derivatives 18 via the condensation with o-hydroxybenzaldehyde derivatives, the coupling with aryl diazonium salts, or the reaction with phenyl isothiocyanate in presence of KOH followed by phenacyl bromide derivatives respectively.

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.

Agonist-mediated switching of ion selectivity in TPC2 differentially promotes lysosomal function

Ion selectivity is a defining feature of a given ion channel and is considered immutable. Here we show that ion selectivity of the lysosomal ion channel TPC2, which is hotly debated (Calcraft et al., 2009; Guo et al., 2017; Jha et al., 2014; Ruas et al., 2015; Wang et al., 2012), depends on the activating ligand. A high-throughput screen identified two structurally distinct TPC2 agonists. One of these evoked robust Ca2+-signals and non-selective cation currents, the other weaker Ca2+-signals and Na+-selective currents. These properties were mirrored by the Ca2+- mobilizing messenger, NAADP and the phosphoinositide, PI(3,5)P2, respectively. Agonist action was differentially inhibited by mutation of a single TPC2 residue and coupled to opposing changes in lysosomal pH and exocytosis. Our findings resolve conflicting reports on the permeability and gating properties of TPC2 and they establish a new paradigm whereby a single ion channel mediates distinct, functionally-relevant ionic signatures on demand.

Synthesis, structure-activity relationships, and pharmacokinetic properties of dihydroorotate dehydrogenase inhibitors: 2-cyano-3-cyclopropyl- 3-hydroxy. N-[3'-methyl-4'-(trifluoromethyl)phenyl]propenamide and related compounds

The active metabolite (2) of the novel immunosuppressive agent leflunomide (1) has been shown to inhibit the enzyme dihydroorotate dehydrogenase (DHODH). This enzyme catalyzes the fourth step in de novo pyrimidine biosynthesis. A series of analogues of the active metabolite 2 have been synthesized. Their in vivo biological activity determined in rat and mouse delayed type hypersensitivity has been found to correlate well with their in vitro DHODH potency. The most promising compound (3) has shown activity in rat and mouse collagen (II)-induced arthritis models (ED50 = 2 and 31 mg/kg, respectively) and has shown a shorter half-life in man when compared with leflunomide. Clinical studies in rheumatoid arthritis are in progress.

Synthesis and Biological Activity of a Series of Diaryl-Substituted α-Cyano-β-hydroxypropenamides, a New Class of Anthelmintic Agents

A series of α-cyano-β-hydroxypropenamides was prepared and tested for anthelmintic activity. α-Cyano-β-hydroxy-N--3-propenamide (1) showed good activity against the nematode Nematospirodes dubius in a mixed parasite infection in mice; several of the analogues were also effective against the cestode Hymenolepis nana.In sheep trials, 1 caused 100percent reduction of the hematophagous nematode Haemonchus contortus after a single dose of 20 mg/kg but did not show satisfactory control of Trichostrongylus colubriformis or Ostertagia circumcincta.Against the liver fluke Fasciola hepatica, 1 suppressed egg production but only temporarily, suggesting that the adult flukes were not eliminated.Mechanism of action studies on 1 using Ascaris mitochondria showed it to be an uncoupler of oxidative phosphorylation.