22272-31-7

Basic information

• Product Name: 2-chloro-3-[(2-methylpropyl)amino]naphthalene-1,4-dione
• Synonyms: 2-chloro-3-(isobutylamino)-1,4-dihydronaphthalene-1,4-dione
• CAS NO: 22272-31-7
• Molecular Formula: C₁₄H₁₄ClNO₂
• Molecular Weight: 263.7195
• Mol File: 22272-31-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 359.5°C at 760 mmHg
• Flash Point: 171.2°C
• Density: 1.26g/cm³
• Vapor Pressure: 2.37E-05mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 2-chloro-3-[(2-methylpropyl)amino]naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-3-[(2-methylpropyl)amino]naphthalene-1,4-dione(22272-31-7)
• EPA Substance Registry System: 2-chloro-3-[(2-methylpropyl)amino]naphthalene-1,4-dione(22272-31-7)

Safety Data

• Hazardous Substances Data: 22272-31-7(Hazardous Substances Data)

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 78-81-9 isobutylamine 

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.

Antiproliferative, DNA intercalation and redox cycling activities of dioxonaphtho[2,3-d]imidazolium analogs of YM155: A structure-activity relationship study

The anticancer agent YM155 is widely investigated as a specific survivin suppressant. More recently, YM155 was found to induce DNA damage and this has raised doubts as to whether survivin is its primary target. In an effort to assess the contribution of DNA damage to the anticancer activity of YM155, several analogs were prepared and evaluated for antiproliferative activity on malignant cells, participation in DNA intercalation and free radical generation by redox cycling. The intact positively charged scaffold was found to be essential for antiproliferative activity and intercalation but was less critical for redox cycling where the minimal requirement was a pared down bicyclic quinone. Side chain requirements at the N1 and N3 positions of the scaffold were more alike for redox cycling and intercalation than antiproliferative activity, underscoring yet again, the limited structural overlaps for these activities. Furthermore, antiproliferative activities were poorly correlated to DNA intercalation and redox cycling. Potent antiproliferative activity (IC50 9-23 nM), exceeding that of YM155, was found for a minimally substituted methyl analog AB7. Like YM155 and other dioxonaphthoimidazoliums, AB7 was a modest DNA intercalator but with weak redox cycling activity. Thus, the capacity of this scaffold to inflict direct DNA damage leading to cell death may not be significant and YM155 should not be routinely classified as a DNA damaging agent.