Synthesis of a new cytotoxic cephalostatin/ritterazine analogue from hecogenin and 22-epi-hippuristanol.
A new cephalostatin/ritterazine analogue was prepared from the commercially available hecogenin acetate and the natural cytotoxic steroid 22-epi-hippuristanol. The method involved the reductive dimerization of enaminoketones (condensation of alpha-aminoketones) and condensation between an enaminoketone and an alpha-hydroxyketone. The new analogue showed higher cytotoxic activity than the cytotoxic 22-epi-hippuristanol against MDA-MB-231, A-549 and HT-29 cultured tumor cell lines.
Poza
Javier Jesús
JJ
Departamento de Química Fundamental, Facultade de Ciencias, Universidade da Coruña, Campus da Zapateira, 15071 A Coruña, Spain.
Rodríguez
Jaime
J
Jiménez
Carlos
C
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy; D002277:Carcinoma / Q000188:drug therapy; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D015179:Colorectal Neoplasms / Q000188:drug therapy; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D008175:Lung Neoplasms / Q000188:drug therapy; D010619:Phenazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012502:Sapogenins / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013261:Sterols / Q000737:chemistry
D000970:Antineoplastic Agents; D003603:Cytotoxins; D010619:Phenazines; D012502:Sapogenins; D013141:Spiro Compounds; D013256:Steroids; D013261:Sterols; C510125:hippuristanol; C529027:ritterazine A; C454806:cephalostatin I; C007908:hecogenin