title: Enantioselective synthesis and antimicrobial activities of tetrahydro-β-carboline diketopiperazines.
abstract: A series of single isomers tetrahydro-β-carboline diketopiperazines were stereoselectively synthesized starting from l-tryptophan methyl ester hydrochloride and six aldehydes through a four-step reaction including Pictet-Spengler reaction, crystallization-induced asymmetric transformations (CIAT), Schotten-Baumann reaction, and intramolecular ester amidation. The chemical structures were characterized by nuclear magnetic resonance (NMR) and elemental analysis, among which two compounds were determined by x-ray single crystal diffraction. Moreover, antimicrobial activities of all the compounds were also tested.
authors.affiliation: Key Laboratory of Auxiliary Chemistry and Technology for Chemical Industry, Ministry of Education, Shaanxi University of Science & Technology, Xi'an, China.
authors.forename: Yangmin
authors.initials: Y
authors.lastname: Ma
authors.forename: Hao
authors.initials: H
authors.lastname: Wu
authors.forename: Jin
authors.initials: J
authors.lastname: Zhang
authors.forename: Yanchao
authors.initials: Y
authors.lastname: Li
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D000890:Anti-Infective Agents; D002243:Carbolines; D054659:Diketopiperazines
keywords: antimicrobial activity; configuration; crystallization-induced asymmetric transformations; tetrahydro-β-carboline diketopiperazine; x-ray single crystal diffraction