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Usage

Uses

Used in Pharmaceutical Industry:
[1,2,4]Triazino[4,3-a]benzimidazol-4(1H)-one,3-methyl-(9CI) is used as a building block for the synthesis of various pharmaceutical compounds due to its diverse biological activities and potential therapeutic applications.
Used in Drug Discovery and Development:
[1,2,4]Triazino[4,3-a]benzimidazol-4(1H)-one,3-methyl-(9CI) is used as a starting material in drug discovery and development, particularly for the creation of new drugs with anti-inflammatory, antioxidant, and anti-cancer properties.
Used in Chemical Synthesis:
[1,2,4]Triazino[4,3-a]benzimidazol-4(1H)-one,3-methyl-(9CI) is used as a key intermediate in the synthesis of other complex organic compounds, taking advantage of its diverse chemical reactivity and heterocyclic structure.

Upstream product

• 15108-18-6 2-hydrazinobenzimidazole 
• 88281-99-6 Ethyl α-oxopropionate benzimidazol-2-ylhydrazone 
• 139883-61-7 1-amino-2-hydrazinobenzimidazole 
• 1616615-77-0 10-amino-3-methyl-1,2,4-triazino[4,3-a]benzimidazol-4(10H)-one 
• 120341-04-0 1-aminobenzimidazole-2-sulfonic acid 
• 1616615-73-6 10-acetylamino-3-methyl-1,2,4-triazino[4,3-a]benzimidazol-4(10H)-one 
• 134469-07-1 Benzimidazol-2-thiol 
• 88282-00-2 α-Oxopropionic acid benzimidazol-2-ylhydrazone 

Relevant academic research and scientific papers

1-Amino-2-hydrazinobenzimidazole and its reactions with some carbonyl compounds

1-Amino-2-hydrazinobenzimidazole was obtained for the first time by treating 1-aminobenzimidazole-2-sulfonic acid with hydrazine hydrate. This compound readily condensed with aromatic aldehydes involving both amino groups. The condensation with 2,4-pentanedione affords 1-amino-2-(3,5-dimethylpyrazol-1- yl)benzimidazole, and with α-ketoacids in glacial acetic acid yields mixtures of 10-acetylamino-3-R-1,2,4-triazino[4,3-a]benzimidazol-4(10H)-ones and 4-amino-2-R-1,2,4-triazino[2,3-a]benzimidazol-3(4H)-ones.

3-Aryl-[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones: Tricyclic heteroaromatic derivatives as a new class of benzodiazepine receptor ligands

A series of 3-substituted [1,2,4]triazino[4,3-c]benzimidazoles V were prepared and tested at the central benzodiazepine receptor (BzR). These compounds were designed as rigid analogues of the previously described N- benzylindolylglyoxylylamide derivatives IV. The title compounds V showed an affinity which depended directly on the presence of the N(10)-H group and an aromatic ring at position 3. Some of them elicited a 2- or 3-fold higher affinity with respect to that of the indolylglyoxylylamide derivatives IV (R=H). The GABA ratio and [35S]-tert-butylcyclophosphorothionate binding data revealed an efficacy profile of partial inverse agonists/antagonists for compounds 1c,e,f,j,k, and of a partial agonist for 2c. This last compound proved to be effective in antagonizing pentylenetetrazole-induced seizures in mice. Attempts were made to interpret the structure-affinity relationships of compounds V in the light of possible tautomeric equilibria involving the ligands.

Studies on Heterocyclic Compounds. Part VI: Synthesis of Bridgehead Nitrogen Triazine and Pyrimidine Heterocycles

New bridgehead nitrogen containing heterocycles such as thiazolotriazine (IVa and IVb), imidazolotriazine (IVc), triazinotriazine (IVd and IVe) and oxadiazolotriazine (IVf) and several of their derivatives (V) have been prepared by reacting their respective hydrazine (II) with ethylpyruvate and phenyl glycoxalic acid.The diazotization of hydrazine (II) furnished the reactive intermediates (VI) (azido form) and (VII) (tetrazole form) depending on the structure of hydrazines.These intermediates have been used to synthesise bridgehead nitrogen pyrimidine derivatives (VIII) by reacting them with diethyl fumarate.The spectral and chemical evidences show that diazotised products obtained from 2-hydrazino-4-phenyl thiazole (IIa) and 2-hydrazino benzothiazole (IIb) exist in tetrazole form (VIIa) and (VIIb), respectively, whereas the remaining four (IIa-IIf) remain in the azido form (VIc-VIf) in the solid state.