24811-77-6

Basic information

• Product Name: Pyrimido[1,2-a]benzimidazol-2(1H)-one, 3,4-dihydro- (8CI,9CI)
• Synonyms: Pyrimido[1,2-a]benzimidazol-2(1H)-one, 3,4-dihydro- (8CI,9CI)
• CAS NO: 24811-77-6
• Molecular Formula: C10H9N3O
• Molecular Weight: 187.19796
• Product Categories: BENZIMIDAZOLE
• Mol File: 24811-77-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrimido[1,2-a]benzimidazol-2(1H)-one, 3,4-dihydro- (8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimido[1,2-a]benzimidazol-2(1H)-one, 3,4-dihydro- (8CI,9CI)(24811-77-6)
• EPA Substance Registry System: Pyrimido[1,2-a]benzimidazol-2(1H)-one, 3,4-dihydro- (8CI,9CI)(24811-77-6)

Safety Data

• Hazardous Substances Data: 24811-77-6(Hazardous Substances Data)

Upstream product

• 18523-47-2 3-azidopropanoic acid 
• 26893-41-4 1H-benzoimidazol-2-ylamine hydrochloride 
• 934-32-7 1H-benzimidazol-2-amine 
• 814-68-6 acryloyl chloride 
• 51290-77-8 2-(benzylthio)-1H-benzo[d]imidazole 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 506-68-3 bromocyane 
• 1270914-58-3 methyl 3-((2-aminophenyl)amino)propanoate 
• 1514913-99-5 C₁₄H₁₉N₅O 
• 95-54-5 1,2-diamino-benzene 
• 140-88-5 ethyl acrylate 
• 89722-55-4 2-(3-chloropropionylamino)benzimidazole 

Relevant articles and documents

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Discovery of selective fragment-sized immunoproteasome inhibitors

Proteasomes contribute to maintaining protein homeostasis and their inhibition is beneficial in certain types of cancer and in autoimmune diseases. However, the inhibition of the proteasomes in healthy cells leads to unwanted side-effects and significant effort has been made to identify inhibitors specific for the immunoproteasome, especially to treat diseases which manifest increased levels and activity of this proteasome isoform. Here, we report our efforts to discover fragment-sized inhibitors of the human immunoproteasome. The screening of an in-house library of structurally diverse fragments resulted in the identification of benzo[d]oxazole-2(3H)-thiones, benzo[d]thiazole-2(3H)-thiones, benzo[d]imidazole-2(3H)-thiones, and 1-methylbenzo[d]imidazole-2(3H)-thiones (with a general term benzoXazole-2(3H)-thiones) as inhibitors of the chymotrypsin-like (β5i) subunit of the immunoproteasome. A subsequent structure-activity relationship study provided us with an insight regarding growing vectors. Binding to the β5i subunit was shown and selectivity against the β5 subunit of the constitutive proteasome was determined. Thorough characterization of these compounds suggested that they inhibit the immunoproteasome by forming a disulfide bond with the Cys48 available specifically in the β5i active site. To obtain fragments with biologically more tractable covalent interactions, we performed a warhead scan, which yielded benzoXazole-2-carbonitriles as promising starting points for the development of selective immunoproteasome inhibitors with non-peptidic scaffolds.

Solid-phase synthesis of 5-noranagrelide derivatives

Solid-phase synthesis of 1H-benzo[d]imidazo[1,2-a]imidazol-2(3H)-one derivatives employing Fmoc-α-amino acids and nitroaryl fluorides as key building blocks has been developed. The Fmoc-α-amino acids immobilized on Wang resin, equipped with a piperazine carbamate linker, were transformed to o-nitroanilines in two steps. After reduction of the nitro group, the corresponding o-phenylenediamines gave the 2-aminobenzimidazole scaffold by reaction either with cyanogen bromide or with Fmoc-NCS. Cleavage from the polymer support and further cyclization afforded the target compounds. The developed methodology represents a versatile and simple approach for the preparation of various corresponding 1H-benzo[d]imidazo[1,2-a]imidazol-2(3H)- ones from a large number of commercially available building blocks.