title: Efficient synthesis of eudistomin U and evaluation of its cytotoxicity.
abstract: Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis. We describe an efficient, five-step synthesis of eudistomin U by employing two key reactions: a Bischler-Napieralski cyclization and a Suzuki cross coupling. We also describe the cytotoxicity of eudistomin U against various cancer cell lines and human pathogens, in which we observed potent antibacterial activity against Gram-positive bacteria.
authors.affiliation: Providence College, Department of Chemistry and Biochemistry, 1 Cunningham Square, Providence, RI 02918, USA.
authors.forename: Chad M
authors.initials: CM
authors.lastname: Roggero
authors.affiliation: Providence College, Department of Chemistry and Biochemistry, 1 Cunningham Square, Providence, RI 02918, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Giulietti
authors.affiliation: Providence College, Department of Chemistry and Biochemistry, 1 Cunningham Square, Providence, RI 02918, USA. Electronic address: smulcahy@providence.edu.
authors.forename: Seann P
authors.initials: SP
authors.lastname: Mulcahy
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D006801:Humans; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D020102:Mycobacterium smegmatis / Q000187:drug effects / Q000254:growth & development; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013297:Streptococcus pyogenes / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D002243:Carbolines; C088110:eudistomin U
keywords: Antibacterial; Eudistomin U; Palladium catalysis; Suzuki cross coupling; β-Carboline