34108-95-7

Basic information

• Product Name: 2H-NAPHTH[1,2-D]IMIDAZOLE-2-THIONE, 1,3-DIHYDRO-
• Synonyms: 2H-NAPHTH[1,2-D]IMIDAZOLE-2-THIONE, 1,3-DIHYDRO-;2H-Naphth[1,2-d]imidazole-2-thione,1,3-dihydro-(9CI)
• CAS NO: 34108-95-7
• Molecular Formula: C11H8N2S
• Molecular Weight: 200.25962
• Product Categories: BENZIMIDAZOLE
• Mol File: 34108-95-7.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-NAPHTH[1,2-D]IMIDAZOLE-2-THIONE, 1,3-DIHYDRO-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-NAPHTH[1,2-D]IMIDAZOLE-2-THIONE, 1,3-DIHYDRO-(34108-95-7)
• EPA Substance Registry System: 2H-NAPHTH[1,2-D]IMIDAZOLE-2-THIONE, 1,3-DIHYDRO-(34108-95-7)

Safety Data

• Hazardous Substances Data: 34108-95-7(Hazardous Substances Data)

Upstream product

• 91240-93-6 4-chloro-2-nitro-1-naphthylamine 
• 75-15-0 carbon disulfide 
• 938-25-0 1,2-diaminonaphthalene 

Downstream Products

• 37734-99-9 9-(2-nitro-benzylidene)-naphtho[1',2':4,5]imidazo[2,1-b]thiazol-8-one 
• 37734-98-8 9-(4-isopropyl-benzylidene)-naphtho[1',2':4,5]imidazo[2,1-b]thiazol-8-one 
• 37735-02-7 9-(3-phenyl-allylidene)-naphtho[1',2':4,5]imidazo[2,1-b]thiazol-8-one 
• 37734-97-7 9-benzylidene-naphtho[1',2':4,5]imidazo[2,1-b]thiazol-8-one 
• 37735-01-6 9-(4-nitro-benzylidene)-naphtho[1',2':4,5]imidazo[2,1-b]thiazol-8-one 
• 37735-00-5 9-(3-nitro-benzylidene)-naphtho[1',2':4,5]imidazo[2,1-b]thiazol-8-one 

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.