Recombination of diterpenoid structure units: synthesis of antitumor amides bearing functionalized bicyclo[3.2.1]octane ring.
In this work, 23 new amides (14-36) bearing a representative diterpenoid structure unit, the functionalized bicyclo[3.2.1]octane ring, have been synthesized and its antitumor potential is studied. In vitro studies demonstrate that a number of amides with the bicyclo[3.2.1]oct-3-en-2-one subunit are active against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 tumor cell lines. The hybrid derivative, compound 20, was found to be the most potent compound (IC(50)=1.05 microM against HL-60) and more active than cisplatin (DDP), the positive control. Additionally, compound 20 exhibited broad spectrum in vitro anticancer activity with IC(50) values of 1.1-4.3 microM against the five tested cancer cell lines.
Mao
Zewei
Z
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, PR China.
Li
Yan
Y
Chen
Jingbo
J
Wang
Yuanyuan
Y
Zhang
Hongbin
H
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D045744:Cell Line, Tumor; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans
D001643:Bridged Bicyclo Compounds; D004224:Diterpenes