Synthesis and biological properties of benzo-annulated rutaecarpines

Young Hwan Hong; Woo Jin Lee; Seung Ho Lee; Jong Keun Son; Hye Lin Kim; Jung Min Nam; Youngjoo Kwon; Yurngdong Jahng

doi:10.1248/bpb.33.1704

Synthesis and biological properties of benzo-annulated rutaecarpines

Young Hwan Hong, Woo Jin Lee, Seung Ho Lee, Jong Keun Son, Hye Lin Kim, Jung Min Nam, Youngjoo Kwon, Yurngdong Jahng

Department of Pharmaceutical Sciences

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

16 Scopus citations

Abstract

A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2- carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity against topoisomerases (topo) I and II. Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I.

Original language	English
Pages (from-to)	1704-1709
Number of pages	6
Journal	Biological and Pharmaceutical Bulletin
Volume	33
Issue number	10
DOIs	https://doi.org/10.1248/bpb.33.1704
State	Published - 2010

Keywords

Benzorutaecarpine
Cytotoxicity
Fischer indole synthesis
Rutaecarpine
Topoisomerase

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abstract = "A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2- carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity against topoisomerases (topo) I and II. Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I.",

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author = "Hong, {Young Hwan} and Lee, {Woo Jin} and Lee, {Seung Ho} and Son, {Jong Keun} and Kim, {Hye Lin} and Nam, {Jung Min} and Youngjoo Kwon and Yurngdong Jahng",

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T1 - Synthesis and biological properties of benzo-annulated rutaecarpines

AU - Hong, Young Hwan

AU - Lee, Woo Jin

AU - Lee, Seung Ho

AU - Son, Jong Keun

AU - Kim, Hye Lin

AU - Nam, Jung Min

AU - Kwon, Youngjoo

AU - Jahng, Yurngdong

PY - 2010

Y1 - 2010

N2 - A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2- carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity against topoisomerases (topo) I and II. Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I.

AB - A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2- carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity against topoisomerases (topo) I and II. Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I.

KW - Benzorutaecarpine

KW - Cytotoxicity

KW - Fischer indole synthesis

KW - Rutaecarpine

KW - Topoisomerase

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AN - SCOPUS:77958008285

SN - 0918-6158

VL - 33

SP - 1704

EP - 1709

JO - Biological and Pharmaceutical Bulletin

JF - Biological and Pharmaceutical Bulletin

IS - 10

ER -

Synthesis and biological properties of benzo-annulated rutaecarpines

Abstract

Keywords

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