Glycosylated nordihydroguaiaretic acids as anti-cancer agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 21; no. 1; pp. 380 - 382
• Main Authors: Hwu, Jih Ru, Hsu, Chuan-I, Hsu, Ming-Hua, Liang, Yu-Chuan, Huang, Ru Chih C., Lee, Yuan C.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01-01-2011; Elsevier
• Subjects: Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - therapeutic use; Biological and medical sciences; Carcinoma, Hepatocellular - drug therapy; Cell Line, Tumor; Galactosides - chemical synthesis; Galactosides - chemistry; Galactosides - therapeutic use; General aspects; Glucosides - chemical synthesis; Glucosides - chemistry; Glucosides - therapeutic use; Glycosylation; Hepatocellular carcinoma; hepatoma; Humans; Liver Neoplasms - drug therapy; Masoprocol - analogs & derivatives; Masoprocol - chemical synthesis; Masoprocol - chemistry; Masoprocol - therapeutic use; Medical sciences; NDGA; Nordihydroguaiaretic acid; Pharmacology. Drug treatments; Triazol-galactose; Triazol-glucose; Triazoles - chemical synthesis; Triazoles - chemistry; Triazoles - therapeutic use; water solubility; Hepatocellular carcinoma; NDGA; Triazol-galactose; Nordihydroguaiaretic acid; Triazol-glucose; Antineoplastic agent; Human; Aldose; Glycosylation; In vitro; Biological activity; Hepatocyte; Triazole derivatives; Water solubility; Glycoside; Masoprocol; Chemical synthesis; Tumor cell; Physicochemical properties
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2010.10.137

Perglycosylated nordihydroguaiaretic acids were synthesized through the Huiseng 1,3-dipolar cycloaddition reaction, which possessed good water solubility and activity against Hep3B cell line.
Three perglycosylated nordihydroguaiaretic acids (NDGA) were synthesized through the Huiseng 1,3-dipolar cycloaddition reaction. These sugar–NDGA conjugates containing triazole-linkages possessed good solubility in water. NDGA-(triazol-galactose)4 (12b) and NDGA-(triazol-glucose)4 (12c) were found to act as inhibitors against human hepatocellular carcinoma Hep3B cells in culture.