Iodine-catalyzed etherification of morroniside

Fortunatus Sunghwa; Hiroaki Sakurai; Ikuo Saiki; Mamoru Koketsu

doi:10.1248/cpb.57.112

Iodine-catalyzed etherification of morroniside

Fortunatus Sunghwa, Hiroaki Sakurai, Ikuo Saiki, Mamoru Koketsu^*

^*Corresponding author for this work

Cancer Cell Biology

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26- L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC₅₀ values equal to 20.9 μM.

Original language	English
Pages (from-to)	112-115
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	57
Issue number	1
DOIs	https://doi.org/10.1248/cpb.57.112
State	Published - 2009/01

Keywords

Cytotoxicity
Etherification
Morroniside

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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title = "Iodine-catalyzed etherification of morroniside",

abstract = "In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26- L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 μM.",

keywords = "Cytotoxicity, Etherification, Morroniside",

author = "Fortunatus Sunghwa and Hiroaki Sakurai and Ikuo Saiki and Mamoru Koketsu",

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AU - Sunghwa, Fortunatus

AU - Sakurai, Hiroaki

AU - Saiki, Ikuo

AU - Koketsu, Mamoru

PY - 2009/1

Y1 - 2009/1

N2 - In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26- L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 μM.

AB - In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26- L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 μM.

KW - Cytotoxicity

KW - Etherification

KW - Morroniside

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Iodine-catalyzed etherification of morroniside

Abstract

Keywords

ASJC Scopus subject areas

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