Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

作者：Bonifazi Evelyn L; Rios Luci Carla; Leon Leticia G; Burton Gerardo; Padron Jose M^*; Misico Rosana I

来源：Bioorganic & Medicinal Chemistry, 2010, 18(7): 2621-2630.

DOI：10.1016/j.bmc.2010.02.032

• Naphthoquinone
• Lapachone
• Lapachol
• Antiproliferative

A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their anti-proliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-( prop-1-en-2-yl) naphtho[2,3-b] furan-4,9-dione (27) were the most potent antiproliferative agents with GI(50) values of 0.42-8.1 and 0.80-2.2 mu M, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity.

• 出版日期2010-4