Pharmacological importance of optically active tetrahydro-β-carbolines and synthetic approaches to create the C1 stereocenter.
1,2,3,4-Tetrahydro-β-carbolines (THβCs) are a pharmacologically important group of compounds belonging to the indole alkaloids. C1-Substituted optically active THβCs have been the target of extensive synthetic efforts due to the presence of the scaffold in numerous natural products and synthetic targets. This review briefly summarizes the methods to obtain the C1 stereocenter and concentrates on evaluating the pharmacological importance of optically active C1-substituted THβCs, including their PDE5-inhibitory, antimalarial, antiviral and antitumor activities.
Laboratory of Organic Chemistry, Department of Chemistry, School of Chemical Tehcnology, Aalto University, PO Box 16100, Kemistintie 1, Aalto FI-00076, Finland. aino.laine@aalto.fi.
Aino E
AE
Laine
Laboratory of Organic Chemistry, Department of Chemistry, School of Chemical Tehcnology, Aalto University, PO Box 16100, Kemistintie 1, Aalto FI-00076, Finland. christopher.lood@aalto.fi.
Christopher
C
Lood
Laboratory of Organic Chemistry, Department of Chemistry, School of Chemical Tehcnology, Aalto University, PO Box 16100, Kemistintie 1, Aalto FI-00076, Finland. ari.koskinen@aalto.fi.
Ari M P
AM
Koskinen
D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004365:Drugs, Chinese Herbal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D058986:Phosphodiesterase 5 Inhibitors / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000962:Antimalarials; D000998:Antiviral Agents; D001688:Biological Products; D002243:Carbolines; D004365:Drugs, Chinese Herbal; D026121:Indole Alkaloids; D058986:Phosphodiesterase 5 Inhibitors; C541947:antitumor A; C009804:tryptoline