4497-72-7

Basic information

• Product Name: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-ethylacetamide
• Synonyms: 1,4-Naphthoquinone, 2-(N-ethylacetamido)-3-chloro-; 2-Chloro-3-(N-ethylacetamido)-1,4-naphthoquinone; 2-Chloro-3-[N-ethylacetamido]-1,4-naphthoquinone; Acetamide, N-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)-N-ethyl-; N-(3-Chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-ethylacetamide
• CAS NO: 4497-72-7
• Molecular Formula: C₁₄H₁₂ClNO₃
• Molecular Weight: 277.703
• Mol File: 4497-72-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 406.8°C at 760 mmHg
• Flash Point: 199.8°C
• Density: 1.35g/cm³
• Vapor Pressure: 7.94E-07mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-ethylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-ethylacetamide(4497-72-7)
• EPA Substance Registry System: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-ethylacetamide(4497-72-7)

Safety Data

• Hazardous Substances Data: 4497-72-7(Hazardous Substances Data)

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 5349-87-1 2-chloro-3-(ethylamino)naphthalene-1,4-dione 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Antimalarial N1, N3-Dialkyldioxonaphthoimidazoliums: Synthesis, Biological Activity, and Structure-activity Relationships

Here we report the nanomolar potencies of N1,N3-dialkyldioxonaphthoimidazoliums against asexual forms of sensitive and resistant Plasmodium falciparum. Activity was dependent on the presence of the fused quinone-imidazolium entity and lipophilicity imparted by the N1/N3 alkyl residues on the scaffold. Gametocytocidal activity was also detected, with most members active at IC50 1 μM. A representative analog with good solubility, limited PAMPA permeability, and microsomal stability demonstrated oral efficacy on a humanized mouse model of P. falciparum.

Dioxonaphthoimidazoliums are Potent and Selective Rogue Stem Cell Clearing Agents with SOX2-Suppressing Properties

Pluripotent stem cells are uniquely positioned for regenerative medicine, but their clinical potential can only be realized if their tumorigenic tendencies are decoupled from their pluripotent properties. Deploying small molecules to remove remnant undifferentiated pluripotent cells, which would otherwise transform into teratomas and teratomacarcinomas, offers several advantages over non-pharmacological methods. Dioxonapthoimidazolium YM155, a survivin suppressant, induced selective and potent cell death of undifferentiated stem cells. Herein, the structural requirements for stemotoxicity were investigated and found to be closely aligned with those essential for cytotoxicity in malignant cells. There was a critical reliance on the quinone and imidazolium moieties but a lesser dependence on ring substituents, which served mainly to fine-tune activity. Several potent analogues were identified which, like YM155, suppressed survivin and decreased SOX2 in stem cells. The decrease in SOX2 would cause an imbalance in pluripotent factors that could potentially prompt cells to differentiate and hence decrease the risk of aberrant teratoma formation. As phosphorylation of the NF-κB p50 subunit was also suppressed, the crosstalk between phospho-p50, SOX2, and survivin could implicate a causal role for NF-κB signaling in mediating the stem cell clearing properties of dioxonaphthoimidazoliums.