5649-75-2

Basic information

• Product Name: 2H-Naphth[1,2-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)
• Synonyms: 2H-Naphth[1,2-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)
• CAS NO: 5649-75-2
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.19402
• Product Categories: BENZIMIDAZOLE
• Mol File: 5649-75-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Naphth[1,2-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Naphth[1,2-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)(5649-75-2)
• EPA Substance Registry System: 2H-Naphth[1,2-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)(5649-75-2)

Safety Data

• Hazardous Substances Data: 5649-75-2(Hazardous Substances Data)

Upstream product

• 861778-39-4 (2-amino-[1]naphthyl)-hydrazine-N,N'-dicarboxylic acid bis-methylamide 
• 75-44-5 phosgene 
• 938-25-0 1,2-diaminonaphthalene 
• 201230-82-2 carbon monoxide 
• 530-62-1 1,1'-carbonyldiimidazole 
• 91-59-8 naphthalen-2-ylamine 
• 91240-93-6 4-chloro-2-nitro-1-naphthylamine 

Relevant articles and documents

Synthesis and biological activity of splitomicin analogs targeted at human NAD+-dependent histone deacetylases (sirtuins)

Small molecules interfering with posttranslational modification of histones are of interest as tools to study epigenetic regulation of gene transcription. Specifically, drugs that interfere with histone deacetylation could be useful to induce differentiation, growth arrest as well as apoptotic cell death in tumor cells. One class of histone deacetylases is known as sirtuins some of which (Saccharomyces cerevisiae Sir2) are for example inhibited by the lactone splitomicin leading to telomeric silencing in yeast. However, splitomicin is only a micromolar inhibitor of yeast Sir2 and does not inhibit human subtypes and the lactone is prone to hydrolytic ring opening. In preliminary SAR-studies, splitomicin analogs lacking this hydrolytically labile ring were described as inactive while the naphthalene moiety could successfully be replaced by smaller aromatic rings in a fragment-like dihydrocoumarin. Here we report the synthesis and biological activity of a series of hydrolytically stable analogs with activity against human SIRT1 and 2. These comparatively small compounds characterized by high ligand efficiency are used as a starting point toward the development of specific inhibitors of histone deacetylases from the class of sirtuins.

A New Synthesis of Cyclic Ureas, Cyclic Urethanes, and a Quinazolinedione. Selenium-Assisted Carbonylation of Aromatic Amines with Carbon Monoxide

Five-, six-, and seven-membered cyclic ureas were synthesized in excellent yields from various aromatic diamines by reaction with carbon monoxide and a stoichiometric or excess amount of selenium in the presence of an oxidizing agent such as oxygen or dimethyl sulfoxide producing selectively the five- and six-membered cyclic ureas.In the case of 2-(2-aminoethyl)aniline under the catalytic conditions, intra- and intermolecular carbonylation competed resulting in the formation of a mixture of the seven-membered cyclic urea, 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one and the acyclic urea, 1,3-bisurea.The distribution ratio of these two products varied depending on the reaction conditions, but selective formation of the cyclic urea was attained only when a stoichiometric or excess amount of selenium was used.In addition to the above diamino compounds, 2-carbamoylaniline, 2-amino-3-pyridinol, and 2-(hydroxymethyl)-aniline also underwent similar carbonylation to give 2,4(1H,3H)-quinazolinedione, oxazolopyridin-2-(3H)-one, and 1,4-dihydro-2H-3,1-benzoxazin-2-one, respectively.