Efficient synthesis and biological evaluation of 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones.
The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with amines in the presence of a catalytic amount of RO(-)Na(+) to give the 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones 6 in good yields. Compound 6 exhibited cytotoxicity against various cancer cells. For example, compounds 6b showed the best inhibition activities against KB, HepG2 and OVCAR3 with IC(50) 9.5, 20.4 and 10.0 microM.
Huang
Nian-Yu
NY
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, Hubei 430079, PR China.
Liang
Yong-Ju
YJ
Ding
Ming-Wu
MW
Fu
Li-Wu
LW
He
Hong-Wu
HW
D002384:Catalysis; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor / Q000379:methods*; D005260:Female; D006801:Humans; D007097:Imines / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D017953:Isocyanates / Q000737:chemistry; D008956:Models, Chemical; D010753:Phosphoranes / Q000737:chemistry; D011688:Purinones / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared / Q000379:methods
D007097:Imines; D017953:Isocyanates; D010753:Phosphoranes; D011688:Purinones