230313-64-1

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 5468-66-6 2-(4-chlorobenzyl)-1H-benzo[d]imidazole 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Preparation of 1,2-substituted benzimidazolesviaa copper-catalyzed three component coupling reaction

1,2-Substituted benzimidazoles were prepared by simply stirring a mixture of copper catalysts,N-substitutedo-phenylenediamines, sulfonyl azides and terminal alkynes. Particularly, the intermediateN-sulfonylketenimine occurred with two nucleophilic addition and the sulfonyl group was eliminatedviacyclization. In a way, sulfonyl azides and copper catalysts activated the terminal alkynes to synthesize benzimidazoles.

Benzimidazole derivatives endowed with potent antileishmanial activity

Two sets of benzimidazole derivatives were synthesised and tested in vitro for activity against promastigotes of Leishmania tropica and L. infantum. Most of the tested compounds resulted active against both Leishmania species, with IC50 values in the low micromolar/sub-micromolar range. Among the set of 2-(long chain)alkyl benzimidazoles, whose heterocyclic head was quaternised, compound 8 resulted about 100-/200-fold more potent than miltefosine, even if the selectivity index (SI) versus HMEC-1 cells was only moderately improved. In the set of 2-benzyl and 2-phenyl benzimidazoles, bearing a basic side chain in position 1, compound 28 (2-(4-chlorobenzyl)-1-lupinyl-5-trifluoromethylbenzimidazole) was 12-/7-fold more potent than miltefosine, but exhibited a further improved SI. Therefore, compounds 8 and 28 represent interesting hit compounds, susceptible of structural modification to improve their safety profiles.

One-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via cascade reactions of o-aminoanilines or naphthalene-1,8-diamine with alkynes and p-tolylsulfonyl azide

A one-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via the cascade reactions of o-aminoanilines or naphthalene-1,8-diamine with terminal alkynes and p-tolylsulfonyl azide is reported. The protocol is efficient and general. Georg Thiem