A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity.
A synthetic approach to analogues of the terpenoid natural product antheminone A is described which employs (-)-quinic acid as starting material. A key conjugate addition step proved to be unpredictable regarding its stereochemical outcome however the route allowed access to two diastereoisomeric series of compounds. The results of biological assay of the toxicity of the target compounds towards non-small-cell lung cancer cell line A549 are reported.
School of Chemistry, University of Manchester, Manchester, UK.
Stephania
S
Christou
Emel
E
Ozturk
Robin G
RG
Pritchard
Peter
P
Quayle
Ian J
IJ
Stratford
Roger C
RC
Whitehead
Katharine F
KF
Williams
D000096:Acetone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000972:Antineoplastic Agents, Phytogenic; D001688:Biological Products; D003512:Cyclohexanones; C528888:antheminone A; D000096:Acetone
Anti-cancer; Natural product; Quinic acid; Synthetic analogue