Synthesis of gamma-hydroxybutenolides applying crossed aldol condensation in the presence of a bulky lewis acid and their anti-tumor activity.

Abstract

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.

• Authors: Yumiko Yamano, Yumi Fujita, Yukari Mizuguchi, Kimie Nakagawa, Toshio Okano, Masayoshi Ito, Akimori Wada
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 55 Issue 9 Pg. 1365-70 (Sep 2007) ISSN: 0009-2363 [Print] Japan
• PMID: 17827763 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Aldehydes
• Antineoplastic Agents
• CD11b Antigen
• Indicators and Reagents
• Lipopolysaccharide Receptors
• Sodium Oxybate
• Thymidine

Topics

• Aldehydes (chemistry)
• Antineoplastic Agents (chemical synthesis, pharmacology)
• CD11b Antigen (biosynthesis)
• Chromatography, High Pressure Liquid
• Flow Cytometry
• HL-60 Cells
• Humans
• Indicators and Reagents
• Lipopolysaccharide Receptors (biosynthesis)
• Magnetic Resonance Spectroscopy
• Sodium Oxybate (chemical synthesis, pharmacology)
• Spectrophotometry, Infrared
• Spectrophotometry, Ultraviolet
• Thymidine (metabolism)