Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from Tabebuia Plants

被引：29

作者：

Inagaki, Ryuta ^{[1
]}

Ninomiya, Masayuki ^{[1
]}

Tanaka, Kaori ^{[2
,3
]}

Watanabe, Kunitomo ^{[2
,3
]}

Koketsu, Mamoru ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan

[2] Gifu Univ, Life Sci Res Ctr, Div Anaerobe Res, Gifu 5011193, Japan

[3] Gifu Univ, United Grad Sch Drug Discovery & Med Informat Sci, Gifu 5011194, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2013年 / 61卷 / 06期

关键词：

furonaphthoquinone; Tabebuia plant; Sonogashira coupling; antileukemic activity; FURANONAPHTHOQUINONES; NAPHTHOQUINONES; DERIVATIVES; DEATH;

D O I：

10.1248/cpb.c13-00011

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Furonaphthoquinones are promising skeletons for anticancer drug molecules. In particular, methoxylated furonaphthoquinones are characteristic constituents of Tabebuia plants. In this research, we synthesized the furonaphthoquinones by effective one-pot cascade reactions of 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetra-hydronaphthalenides with 3-butyn-2-ol in the presence of palladium and cuprous catalysts via Sonogashira coupling and intramolecular cyclization. Furthermore, we demonstrated that the synthetic furonaphthoquinones showed moderate cytotoxicity against human leukemia U937 and HL-60 cells. Our work highlights the importance of furonaphthoquinones as antileukemic agents.

引用

页码：670 / 673

页数：4

共 24 条

[1]

ABBOTT BJ, 1967, CANCER RES, V27, P190

[2] 4-Hydroxyderricin from Angelica keiskei Roots Induces Caspase-dependent Apoptotic Cell Death in HL60 Human Leukemia Cells [J].

Akihisa, Toshihiro ;

Kikuchi, Takashi ;

Nagai, Hisashi ;

Ishii, Koichi ;

Tabata, Keiichi ;

Suzuki, Takashi .

JOURNAL OF OLEO SCIENCE, 2011, 60 (02) :71-77

[3]

DEOLIVEIRA AB, 1993, PHYTOCHEMISTRY, V34, P1409, DOI 10.1016/0031-9422(91)80039-4

[4] Furanonaphthoquinones from Tabebuia ochracea ssp neochrysanta [J].

Diaz, F ;

Medina, JD .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (04) :423-424

[5] Sentulic acid: A cytotoxic ring A-seco triterpenoid from Sandoricum koetjape Merr [J].

Efdi, Mai ;

Ninomiya, Masayuki ;

Suryani, Erma ;

Tanaka, Kaori ;

Ibrahim, Sanusi ;

Watanabe, Kunitomo ;

Koketsu, Mamoru .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (13) :4242-4245

[6] Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol [J].

Eyong, Kenneth O. ;

Kumar, Ponminor S. ;

Kuete, Victor ;

Folefoc, Gabriel N. ;

Nkengfack, Ephriam A. ;

Baskaran, Sundarababu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (20) :5387-5390

[7]

Hatzigrigoriou E., 1988, LIEBIGS ANN CHEM, V2, P167, DOI [10.1002/jlac.198919890132, DOI 10.1002/JLAC.198919890132]

[8] Furanonaphthoquinone analogs possessing preferential antitumor activity compared to normal cells [J].

Hirai, KI ;

Koyama, J ;

Pan, JH ;

Simamura, E ;

Shimada, H ;

Yamori, T ;

Sato, S ;

Tagahara, K ;

Tsuruo, T .

CANCER DETECTION AND PREVENTION, 1999, 23 (06) :539-550

[9] Enyne synthesis through a modified Sonogashira cross-coupling reaction catalyzed by cyclopalladated complexes [J].

Huang, Mengmeng ;

Feng, Yujian ;

Wu, Yangjie .

TETRAHEDRON, 2012, 68 (01) :376-381

[10] A GENERAL METHOD OF PREPARATION OF SUBSTITUTED 2-HYDROXY-1,4-QUINONES [J].

KASTURI, TR ;

ARUNACHA.T .

CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (09) :1086-&

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