Combinatorial solid-phase synthesis of 6-hydroxy-1,2,3,4-tetrahydro-beta-carbolines from l-5-hydroxytryptophan.
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.
Danieli
Bruno
B
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.
Giovanelli
Paola
P
Lesma
Giordano
G
Passarella
Daniele
D
Sacchetti
Alessandro
A
Silvani
Alessandra
A
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
D000470:Alkaloids; D002243:Carbolines; D011137:Polystyrenes; D006916:5-Hydroxytryptophan