The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells.
In this study, we synthesized a series of enantiomerically pure (2R,3S)-disubstituted tetrahydropyranes with diverse functional groups using known methodologies. In addition to the tert-butyl dimethyl silyl group, other common protecting groups for hydroxyl groups such as allyl, acetate, and benzoate were used to obtain appropriate derivatives. Pure compounds were evaluated in vitro against HL60 human leukemia cells and MCF7 human breast cancer cells. From the growth inhibition data a structure-activity relationship was obtained. Overall the results point to the relevant role of the tert-butyl dimethyl silyl group in the modulation of cytotoxic activity.
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain.
Osvaldo J
OJ
Donadel
Tomás
T
Martín
Víctor S
VS
Martín
Jesús
J
Villar
José M
JM
Padrón
D000085:Acetates / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry; D001943:Breast Neoplasms / Q000473:pathology; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007938:Leukemia / Q000473:pathology; D017646:Organosilicon Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D004364:Pharmaceutical Preparations; D011714:Pyrans / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000085:Acetates; D000498:Allyl Compounds; D000970:Antineoplastic Agents; D001565:Benzoates; D017646:Organosilicon Compounds; D004364:Pharmaceutical Preparations; D011714:Pyrans; C009660:t-butyldimethylsilyl compounds