title: Design and synthesis of new biprivileged molecular scaffolds: indolo-fused benzodiazepinyl/quinoxalinyl benzimidazoles.
abstract: The present article describes the design and synthesis of new biprivileged molecular scaffolds with diverse structural features. Commercially available, simple heterocyclic building blocks such as 4-fluoro-3-nitrobenzoic acid, 2-chloro-3-nitrobenzoic acid, and indoline were utilized for the synthesis of the novel heterocycles. Pictet-Spengler-type condensation was used as a key step to construct tetracyclic indolo-benzodiazepines and indolo-quinoxalines linked with substituted benzimidazoles. Analysis of single crystals of representative compounds showed that these molecular skeletons have the potential to present various substituents with distinct three-dimensional orientations.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan.
authors.forename: Indrajeet J
authors.initials: IJ
authors.lastname: Barve
authors.forename: Chan-Yu
authors.initials: CY
authors.lastname: Chen
authors.forename: Deepak B
authors.initials: DB
authors.lastname: Salunke
authors.forename: Wen-Sheng
authors.initials: WS
authors.lastname: Chung
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
mesh_terms: D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D001569:Benzodiazepines / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001562:Benzimidazoles; D007211:Indoles; D011810:Quinoxalines; D001569:Benzodiazepines