Syntheses and cytotoxicities of the analogues of the taxoid brevifoliol.
Seven novel brevifoliol analogues have been synthesized by coupling brevifoliol and 2-monosubstituted-4-phenyl-1,3-oxazolidine carboxylic acid after removal of the protecting group with acid treatment. Brevifoliol and its synthesized analogues were tested for their cytotoxic activities against four different human cancer cell lines, oral (KB), breast (MCF-7), colon (CaCO2) and liver (HepG-2) as determined by MTT assay. The C-13 oxidized brevifoliol retained significant activity. Out of the seven analogues synthesized, C-13 oxidized brevifoliol-5-[N-tert-butoxycarbonyl amino-(2'R,3'S)-3'-phenyl isoserine] analogue was interesting as it exhibited selective and potent cytotoxicity against liver cancer cell line predominantly.
Chattopadhyay
Sunil K
SK
Central Institute of Medicinal and Aromatic Plants (CIMAP), PO CIMAP, Lucknow, India. chattsk@yahoo.com
Tripathi
Sarita
S
Darokar
Mahendra P
MP
Faridi
Uzma
U
Sisodia
Brijesh
B
Negi
Shubhra
S
Kotesh Kumar
J
J
Khanuja
Suman P S
SP
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000633:toxicity*; D045744:Cell Line, Tumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D043823:Taxoids / Q000138:chemical synthesis* / Q000633:toxicity*
D000972:Antineoplastic Agents, Phytogenic; D043823:Taxoids; C487077:brevifoliol