title: Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: syntheses and applications.
abstract: Natural monoterpenes have proved to be good starting materials for the synthesis of β-amino acid derivatives. In the past decade, a number of well-known synthetic procedures have been applied for the preparation of monoterpene-based β-amino acid derivatives, e.g. from β-lactams via the 1,2-dipolar cycloaddition of chlorosulfonyl isocyanate to commercial or readily available monoterpenes [e.g. (+)- and (-)-α- or δ-pinene, (+)-3- and 2-carene, (+)- and (-)-apopinene], the conjugate addition of amides to monoterpene-based α,β-unsaturated esters or the transformations of (-)-cis-pinonoic acid prepared by the oxidative cleavage of (+)- and (-)-verbenone. β-Amino acid derivatives are excellent building blocks for versatile transformations, e.g. multicomponent reactions resulting in β-lactams, syntheses of 1,3-heterocycles and diaminopyrimidine derivatives or the formation of peptides containing an H12 helix. 1,3-Amino alcohol derivatives prepared from β-amino esters have been applied as chiral catalysts in enantioselective transformations. Several of these compounds are of noteworthy pharmacological importance, such as tyrosine kinase Axl inhibitor diaminopyrimidine-coupled β-aminocarboxamides, MDR inhibitor thiourea derivatives of β-amino esters or 2-imino-1,3-oxazines, which exhibit marked growth inhibitory activity on multiple cancer cell lines. The present review summarizes recent developments relating to the syntheses, applications and pharmaceutical importance of monoterpene-based β-amino acids and their derivatives.
authors: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged 6720, Hungary.
authors: Zsolt
authors: Z
authors: Szakonyi
authors: Ferenc
authors: F
authors: Fülöp
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000081008:Bicyclic Monoterpenes; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D039821:Monoterpenes / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000494:pharmacology; D013890:Thiourea / Q000737:chemistry; D047090:beta-Lactams / Q000737:chemistry
chemical_list: D000596:Amino Acids; D000081008:Bicyclic Monoterpenes; D004952:Esters; D039821:Monoterpenes; D010455:Peptides; D013729:Terpenes; D047090:beta-Lactams; C030216:pinane; C113988:2-carene; D013890:Thiourea