Synthesis of gamma-hydroxybutenolides applying crossed aldol condensation in the presence of a bulky lewis acid and their anti-tumor activity.
An improved synthesis of gamma-hydroxybutenolides 1a-d was achieved via crossed aldol condensation between aldehydes 2a-d and the protected gamma-hydroxy-beta-methylbutenolides 3 or 4 using the bulky Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH). Using this same methodology, the gamma-hydroxybutenolides 17a-d having various heteroaromatic rings were synthesized and their anti-tumor activities were evaluated.
Yamano
Yumiko
Y
Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Kobe, Japan. y-yamano@kobepharma-u.ac.jp
Fujita
Yumi
Y
Mizuguchi
Yukari
Y
Nakagawa
Kimie
K
Okano
Toshio
T
Ito
Masayoshi
M
Wada
Akimori
A
D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D039481:CD11b Antigen / Q000096:biosynthesis; D002851:Chromatography, High Pressure Liquid; D005434:Flow Cytometry; D018922:HL-60 Cells; D006801:Humans; D007202:Indicators and Reagents; D018950:Lipopolysaccharide Receptors / Q000096:biosynthesis; D009682:Magnetic Resonance Spectroscopy; D012978:Sodium Oxybate / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013936:Thymidine / Q000378:metabolism