Expedient synthesis and structure-activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids.
The total synthesis of alkaloids phenanthroindolizidine 1a, tylophorine 1b, and phenanthroquinolizidine 1c, has been achieved in 46%, 49%, and 42% overall yield, respectively, starting from the corresponding phenanthrene-9-carboxaldehyde. Compound exhibited potent inhibition activity in three human cancer cell lines, with IC(50) values ranging from 104 to 130 nM. The structure-activity relations of these alkaloids and some of their synthetic intermediates against the three cell lines were also described.
Chuang
Ta-Hsien
TH
Department of Chemistry, National Cheng Kung University, Tainan, 701, Taiwan, ROC.
Lee
Shiow-Ju
SJ
Yang
Cheng-Wei
CW
Wu
Pei-Lin
PL
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D001671:Biochemistry / Q000379:methods*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry; D010618:Phenanthrolines / Q000138:chemical synthesis / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000470:Alkaloids; D000970:Antineoplastic Agents; D007212:Indolizines; D010616:Phenanthrenes; D010618:Phenanthrolines; D011807:Quinolizines; C521640:phenanthroindolizidine; C521641:phenanthroquinolizidine; C004218:tylophorine