Synthesis of benzo-annulated tryptanthrins and their biological properties

Jing Lu Liang; So Eun Park; Youngjoo Kwon; Yurngdong Jahng

doi:10.1016/j.bmc.2012.06.034

Synthesis of benzo-annulated tryptanthrins and their biological properties

Jing Lu Liang, So Eun Park, Youngjoo Kwon, Yurngdong Jahng

Department of Pharmaceutical Sciences

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

44 Scopus citations

Abstract

A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials.

Original language	English
Pages (from-to)	4962-4967
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	16
DOIs	https://doi.org/10.1016/j.bmc.2012.06.034
State	Published - 15 Aug 2012

Bibliographical note

Funding Information:
Financial support from Korean Science Foundation (KRF-2008-521-E00189) and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010-0002646) are gratefully acknowledged.

Keywords

3-Amino-2-naphthoic acid
Benzotryptanthrin
Cytotoxicity
Isatin
Isatoic anhydride
Topoisomerase I
Topoisomerase II
Tryptanthrin

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10.1016/j.bmc.2012.06.034

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title = "Synthesis of benzo-annulated tryptanthrins and their biological properties",

abstract = "A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials.",

keywords = "3-Amino-2-naphthoic acid, Benzotryptanthrin, Cytotoxicity, Isatin, Isatoic anhydride, Topoisomerase I, Topoisomerase II, Tryptanthrin",

author = "Liang, {Jing Lu} and Park, {So Eun} and Youngjoo Kwon and Yurngdong Jahng",

note = "Funding Information: Financial support from Korean Science Foundation (KRF-2008-521-E00189) and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010-0002646) are gratefully acknowledged.",

year = "2012",

month = aug,

day = "15",

doi = "10.1016/j.bmc.2012.06.034",

language = "English",

volume = "20",

pages = "4962--4967",

journal = "Bioorganic and Medicinal Chemistry",

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T1 - Synthesis of benzo-annulated tryptanthrins and their biological properties

AU - Liang, Jing Lu

AU - Park, So Eun

AU - Kwon, Youngjoo

AU - Jahng, Yurngdong

N1 - Funding Information: Financial support from Korean Science Foundation (KRF-2008-521-E00189) and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010-0002646) are gratefully acknowledged.

PY - 2012/8/15

Y1 - 2012/8/15

N2 - A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials.

AB - A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials.

KW - 3-Amino-2-naphthoic acid

KW - Benzotryptanthrin

KW - Cytotoxicity

KW - Isatin

KW - Isatoic anhydride

KW - Topoisomerase I

KW - Topoisomerase II

KW - Tryptanthrin

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DO - 10.1016/j.bmc.2012.06.034

M3 - Article

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AN - SCOPUS:84864485419

SN - 0968-0896

VL - 20

SP - 4962

EP - 4967

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 16

ER -

Synthesis of benzo-annulated tryptanthrins and their biological properties

Abstract

Bibliographical note

Keywords

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