Carbodiimide-Based Benzimidazole Library Method
- 27 October 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 8 (6), 907-914
- https://doi.org/10.1021/cc060106b
Abstract
Using carbodiimide reagents [1,3-diisopropylcarbodiimide or N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC)], we have developed a mild, generalized, one-pot method that delivers N-2-arylaminobenzimidazole esters from commercially available aryl isothiocyanates and o-phenylenediamines. Following saponification and acidifying, the benzimidazole acids were isolated in overall yields ranging from 75 to 88% from the starting aryl isothiocyanates. Nine benzimidazole acids were converted into a library consisting of 180 benzimidazole amides following EDC coupling with commercially available amines. The National Institute of General Medical Science will dispense these benzimidazole amides to academia groups for pilot scale biomedical studies. Using these mild conditions and environmentally safe reagents, we demonstrated that these pharmaceutically ornate heterocycles can also be constructed on solid support.Keywords
This publication has 31 references indexed in Scilit:
- Combinatorial Synthesis of Benzothiazoles and Benzimidazoles Using a Traceless Aniline LinkerJournal of Combinatorial Chemistry, 2006
- Druggability: selecting optimized drug candidatesDrug Discovery Today, 2005
- Benzimidazoles as new potent and selective DP antagonists for the treatment of allergic rhinitisBioorganic & Medicinal Chemistry Letters, 2004
- The human prostanoid DP receptor stimulates mucin secretion in LS174T cellsBritish Journal of Pharmacology, 2000
- Correlation of carbon‐13 substituent‐induced chemical shifts: Meta‐ and para‐substituted methyl benzoatesMagnetic Resonance in Chemistry, 1989
- A Facile Synthesis of DimethylN-Aryldithiocarbonimidates and 2-ArylaminobenzimidazolesSynthesis, 1983
- Carbodiimide, IV. Über eine neue Synthese aromatischer IsothiocyanateEuropean Journal of Inorganic Chemistry, 1968
- Transposition du p‐nitrophénylsulfonylamino‐benzimidazole: (Propriétés du groupe sulfonyle XIVRecueil des Travaux Chimiques des Pays-Bas, 1950
- 47. The inhibitory effect of substituents in chemical reactions. Part III. The reactivity of the isothiocyano-group in substituted arylthiocarbimidesJournal of the Chemical Society, 1934
- The Synthesis of Heterocyclic Compounds by Means of Isothiourea EthersJournal of the American Chemical Society, 1933