title: Combinatorial solid-phase synthesis of 6-hydroxy-1,2,3,4-tetrahydro-beta-carbolines from l-5-hydroxytryptophan.
abstract: A library of biologically relevant 6-hydroxy-tetrahydro-beta-carbolines (6-OH-THBCs) based on the L-5-OH-tryptophan scaffold was prepared. A solid-phase synthesis was developed, utilizing aminomethyl polystyrene resin and solid-phase-optimized reactions, such as Pictet-Spengler condensation. The library was designed such that three points of diversity would be readily introduced, making the strategy potentially suitable for generation of a large number of compounds.
authors.affiliation: Dipartimento di Chimica Organica e Industriale e Centro Interdisciplinare Studi Biomolecolari e Applicazioni Industriali (CISI), Università degli Studi di Milano, Via G. Venezian 21, 20133 Milano, Italy.
authors.forename: Bruno
authors.initials: B
authors.lastname: Danieli
authors.forename: Paola
authors.initials: P
authors.lastname: Giovanelli
authors.forename: Giordano
authors.initials: G
authors.lastname: Lesma
authors.forename: Daniele
authors.initials: D
authors.lastname: Passarella
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sacchetti
authors.forename: Alessandra
authors.initials: A
authors.lastname: Silvani
mesh_terms: D006916:5-Hydroxytryptophan / Q000737:chemistry*; D000470:Alkaloids / Q000494:pharmacology; D002243:Carbolines / Q000138:chemical synthesis*; D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011137:Polystyrenes / Q000737:chemistry
chemical_list: D000470:Alkaloids; D002243:Carbolines; D011137:Polystyrenes; D006916:5-Hydroxytryptophan