Synthesis and pharmacological evaluation of 5-carboxamide-substituted tetrahydrochromeno[7,8-d]imidazoles
- Resource Type
- Authors
- Andreas Palmer; Wolfgang Kromer; Gabriela Münch; Christian Scheufler
- Source
- Tetrahedron Letters. 50:3920-3922
- Subject
- chemistry.chemical_classification
Benzimidazole
medicine.drug_class
Stereochemistry
Carboxylic acid
Organic Chemistry
Carboxamide
Biological activity
Biochemistry
chemistry.chemical_compound
chemistry
Drug Discovery
medicine
Hofmann rearrangement
Curtius rearrangement
- Language
- ISSN
- 0040-4039
A fast access to novel 5-carboxamide-substituted tetrahydrochromeno[7,8- d ]imidazoles 4 was developed using the readily available preclinical candidate BYK 405879 ( 1 ) as starting material. The 5-amino function was installed by the Curtius rearrangement of carboxylic acid 2 or by the Hofmann rearrangement of carboxamide 8 furnishing benzimidazole 3 as key intermediate. In the Ghosh Schild rat, some of the target compounds 10 – 14 showed noteworthy activity as potassium-competitive acid blockers.