Synthesis and cytotoxicity of triterpenoids derived from betulin and betulinic acid via click chemistry.
In this study, a series of triazole substituted betulin and betulinic acid derivatives was designed and synthesized via click chemistry at C-30 position. Eighteen target compounds were evaluated in vitro for their antitumor activities against leukemia cell-line HL-60. Seventeen compounds have not reported before. The cytotoxic experiment showed that most of betulinic acid derived triazoles have higher cytotoxic profile than betulinic acid. Among them, compound 30-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl] betulinic acid (7b) showed the best IC50 value (1.3 μM) against leukemia cell-line HL-60 (eight- to ninefold higher potency than betulinic acid).
a Department of Chemistry , Zhejiang University , Hangzhou 310027 , China.
Wei
W
Shi
Ning
N
Tang
Wei-Dong
WD
Yan
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D057930:Click Chemistry; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000094062:Betulinic Acid
D000970:Antineoplastic Agents; D053978:Pentacyclic Triterpenes; D014230:Triazoles; D014315:Triterpenes; C002503:betulin; D000094062:Betulinic Acid
betulin; betulinic acid; click chemistry; cytotoxicity; derivatives