133703-76-1Relevant academic research and scientific papers
An efficient one-pot conversion of carboxylic acids into benzimidazoles via an HBTU-promoted methodology
Barasa, Leonard,Yoganathan, Sabesan
, p. 35824 - 35830 (2018/10/31)
Benzimidazole is a privileged, and routinely used pharmacophore in the drug discovery process. Herein, we report a mild, acid-free and one-pot synthesis of indole, alkyl and alpha-amino benzimidazoles through a novel HBTU-promoted methodology. An extensive library of indole-carboxylic acids, alkyl carboxylic acids and N-protected alpha-amino acids has been converted into the corresponding benzimidazoles in 80-99% yield. Since alpha-aminobenzimidazoles are highly useful synthons as chiral ligands for chemical catalysis, as well as for drug discovery endeavors, our reported method provides direct access to this scaffold in a simple, one-pot operation from commercially available carboxylic acids.
Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions
Mohite, Pravinkumar Hansraj,Drabina, Pavel,Bure?, Filip
, p. 1613 - 1622 (2017/03/21)
A straightforward reaction path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared
Investigation of structural mimetics of natural phosphate ion binding motifs
Kataev, Evgeny A.,Shumilova, Tatiana A.
, p. 3354 - 3370 (2015/07/02)
Phosphates are ubiquitous in biology and nearly half of all proteins interact with their partners by means of recognition of phosphate residues. Therefore, a better understanding of the phosphate ion binding by peptidic structures is highly desirable. Two
Benzo[ d ]imidazole and aliphatic α-amino acid derived primary amines in asymmetric aldol reactions
Mohite, Pravinkumar Hansraj,Drabina, Pavel,Bure?, Filip
, p. 491 - 494 (2014/03/21)
Starting from essential α-amino acids, four new benzo[d]imidazole and alkyl-chain-substituted primary amines were synthesized. The reaction sequence involves activation of the Boc-amino acid carboxylic acid, reaction with o-phenylenediamine, and subsequen
Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore
Balboni, Gianfranco,Trapella, Claudio,Sasaki, Yusuke,Ambo, Akihiro,Marczak, Ewa D.,Lazarus, Lawrence H.,Salvadori, Severo
supporting information; experimental part, p. 5556 - 5559 (2010/02/28)
To improve the structure-activity studies of the lead δ opioid agonist H-Dmt-Tic-Asp*-Bid, we synthesized and pharmacologically characterized a series of analogues in which the side chain next to 1H-benzimidazole-2-yl (Bid) was substituted by those endowe
