Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern. 4. Synthesis and biological activity of 2-chloro-3- (substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4- naphthoquinones

He Xi Chang, Ting Chao Chou, Niramol Savaraj, Leroy-Fong Liu, Chiang Yu, C. C. Cheng

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

The intermediate in the preparation of 1,3,7,10- tetrahydroxybenzo[b]naphtho[2,3-d]furan-6,11-dione (2), 2-chloro-5,8- dimethoxy-3-(3,5-dimethoxyphenoxy)-1,4-naphthoquinone (8h), and corresponding hydroxyl, methoxyl, and acetoxyl analogues was found to possess interesting inhibitory activities in a number of cytotoxic test systems. Activities were also noticed in some 5,8-dihydroxy-1,4-naphthoquinone derivatives. A structure-activity discussion of compounds of this series is presented. The newly uncovered biological activity of 2-chloro-3-(substituted phenoxyl)- 1,4-naphthoquinones and 2,3-bis(substituted phenoxy)-1,4-naphthoquinones may suggest an approach for the development of new classes of antineoplastic agents.

Original languageEnglish
Pages (from-to)405-408
Number of pages4
JournalJournal of Medicinal Chemistry
Volume42
Issue number3
DOIs
Publication statusPublished - 1999
Externally publishedYes

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Bioactivity
Antineoplastic Agents
Hydroxyl Radical
Derivatives
naphthazarin
1,4-naphthoquinone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern. 4. Synthesis and biological activity of 2-chloro-3- (substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4- naphthoquinones",
abstract = "The intermediate in the preparation of 1,3,7,10- tetrahydroxybenzo[b]naphtho[2,3-d]furan-6,11-dione (2), 2-chloro-5,8- dimethoxy-3-(3,5-dimethoxyphenoxy)-1,4-naphthoquinone (8h), and corresponding hydroxyl, methoxyl, and acetoxyl analogues was found to possess interesting inhibitory activities in a number of cytotoxic test systems. Activities were also noticed in some 5,8-dihydroxy-1,4-naphthoquinone derivatives. A structure-activity discussion of compounds of this series is presented. The newly uncovered biological activity of 2-chloro-3-(substituted phenoxyl)- 1,4-naphthoquinones and 2,3-bis(substituted phenoxy)-1,4-naphthoquinones may suggest an approach for the development of new classes of antineoplastic agents.",
author = "Chang, {He Xi} and Chou, {Ting Chao} and Niramol Savaraj and Leroy-Fong Liu and Chiang Yu and Cheng, {C. C.}",
year = "1999",
doi = "10.1021/jm9804679",
language = "English",
volume = "42",
pages = "405--408",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "3",

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TY - JOUR

T1 - Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern. 4. Synthesis and biological activity of 2-chloro-3- (substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4- naphthoquinones

AU - Chang, He Xi

AU - Chou, Ting Chao

AU - Savaraj, Niramol

AU - Liu, Leroy-Fong

AU - Yu, Chiang

AU - Cheng, C. C.

PY - 1999

Y1 - 1999

N2 - The intermediate in the preparation of 1,3,7,10- tetrahydroxybenzo[b]naphtho[2,3-d]furan-6,11-dione (2), 2-chloro-5,8- dimethoxy-3-(3,5-dimethoxyphenoxy)-1,4-naphthoquinone (8h), and corresponding hydroxyl, methoxyl, and acetoxyl analogues was found to possess interesting inhibitory activities in a number of cytotoxic test systems. Activities were also noticed in some 5,8-dihydroxy-1,4-naphthoquinone derivatives. A structure-activity discussion of compounds of this series is presented. The newly uncovered biological activity of 2-chloro-3-(substituted phenoxyl)- 1,4-naphthoquinones and 2,3-bis(substituted phenoxy)-1,4-naphthoquinones may suggest an approach for the development of new classes of antineoplastic agents.

AB - The intermediate in the preparation of 1,3,7,10- tetrahydroxybenzo[b]naphtho[2,3-d]furan-6,11-dione (2), 2-chloro-5,8- dimethoxy-3-(3,5-dimethoxyphenoxy)-1,4-naphthoquinone (8h), and corresponding hydroxyl, methoxyl, and acetoxyl analogues was found to possess interesting inhibitory activities in a number of cytotoxic test systems. Activities were also noticed in some 5,8-dihydroxy-1,4-naphthoquinone derivatives. A structure-activity discussion of compounds of this series is presented. The newly uncovered biological activity of 2-chloro-3-(substituted phenoxyl)- 1,4-naphthoquinones and 2,3-bis(substituted phenoxy)-1,4-naphthoquinones may suggest an approach for the development of new classes of antineoplastic agents.

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U2 - 10.1021/jm9804679

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SP - 405

EP - 408

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

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ER -