Synthesis and biological activities of azalamellarins.
The synthesis of azalamellarins, a new series of lactam analogues of biologically active lamellarins, was achieved using Cu(I)-mediated and microwave-assisted C-N(amide) bond formation. Seventeen azalamellarins, including N-allylazalamellarins and N-propylazalamellarins chi-D, L-N, and J-dehydro J, were synthesized and evaluated for their cytotoxicity against the cancer cell lines HuCCA-1, A-549, HepG2, and MOLT-3. The results showed that certain azalamellarins exhibited good activities in the micromolar IC(50) value range (IC(50)=the drug concentration that causes 50 % of cell-growth inhibition after 72 h of continuous exposure to the test molecule), comparable to their parent lamellarin analogue.
Boonya-Udtayan
Sasiwadee
S
Program on Chemical Biology, Center of Excellence on Environmental Health, Toxicology and Management of Chemicals (ETM), Chulabhorn Graduate Institute, Laksi, Bangkok 10210, Thailand.
Yotapan
Nattawut
N
Woo
Christina
C
Bruns
Carson J
CJ
Ruchirawat
Somsak
S
Thasana
Nopporn
N
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D003300:Copper / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D003374:Coumarins; D007769:Lactams; D003300:Copper