Synthesis, structure analysis and cytotoxicity studies of novel unsymmetrically n,n'-substituted ureas from dehydroabietic Acid.
A series of novel unsymmetrically N,N'-substituted ureas were synthesized from dehydroabietic acid and their structures were characterized by IR, 1H-NMR, 13C-NMR spectroscopy and single crystal X-ray diffraction. Three six-membered rings of urea 4c exhibited plane, half-chair and chair configurations, respectively. Their cytotoxicity activities against SMMC7721 liver cancer cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) method. The results showed that the title compounds exhibited highly effective cytotoxicity activities against SMMC7721 cells. Their IC50 values are between 8.8 and 14.2 micromol/l. The change of N' substituted groups resulted little difference to the cytotoxicity activities of ureas, which indicated that the cytotoxicity of this kind of ureas depend strongly on the tricyclic hydrophenanthrene structure.
Rao
Xiaoping
X
Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, PR China. rxping2001@163.com
Song
Zhanqian
Z
He
Ling
L
Jia
Weihong
W
D045784:Abietanes / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014508:Urea / Q000737:chemistry*; D014961:X-Ray Diffraction
D045784:Abietanes; D000970:Antineoplastic Agents; C013913:dehydroabietic acid; D014508:Urea