Journal of Medicinal Chemistry, volume 40, issue 12, pages 1894-1900
Design and Synthesis of Potent Antitumor 5,4‘-Diaminoflavone Derivatives Based on Metabolic Considerations
Tsutomu Akama
1
,
Hiroyuki Ishida
1
,
Yasushi Shida
1
,
Uichiro Kimura
1
,
Katsushige Gomi
1
,
Hiromitsu Saito
1
,
Eiichi Fuse
1
,
Satoshi Kobayashi
1
,
Nobuyuki Yoda
1
,
Masaji Kasai
1
1
Pharmaceutical Research Laboratories, Kyowa Hakko Kogyo Company, Ltd., 1188 Shimotogari, Nagaizumi-cho, Sunto-gun, Shizuoka-ken 411, Japan
|
Publication type: Journal Article
Publication date: 1997-06-01
Journal:
Journal of Medicinal Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 7.3
ISSN: 00222623, 15204804
Drug Discovery
Molecular Medicine
Abstract
Recently, we reported that 5,4‘-diaminoflavone (1) exhibits potent and specific growth-inhibitory activity against the estrogen receptor (ER)-positive human breast cancer cell line MCF-7. However, when compound 1 was incubated with S-9 mix, its metabolites were observed. Moreover, addition of S-9 mix to the medium caused the drastic decrease in activity of compound 1. Since the 6-, 8-, and 3‘-positions were considered to be metabolized oxidatively in vivo from MO calculations, a series of 5,4‘-diaminoflavone derivatives substituted at such putative metabolic positions with various functional groups were synthesized aiming at the metabolically stable derivatives. Among them, 5,4‘-diamino-6,8,3‘-trifluoroflavone (14d) exhibited strong growth-inhibitory activity against MCF-7 cells even in the presence of S-9 mix. Moreover, orally administered compound 14d completely suppressed the growth of MCF-7 inoculated into nude mice, and the effect was more potent than that of compound 1. In addition to ER-positive breast cancer cells, compound 14d exhibited growth-inhibitory activity against a panel of human cancer cell lines including a part of ER-negative breast, endometrial, ovarian, and liver cancers. From these results, fluorine introduction to the putative metabolic positions of compound 1 was elucidated to be effective in the enhancement of the in vivo antitumor activity, probably due to the block of the metabolic deactivation.
Top-30
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1 publication, 2.13%
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1
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3
4
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Citations by publishers
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2
4
6
8
10
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Wiley
10 publications, 21.28%
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Elsevier
9 publications, 19.15%
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Taylor & Francis
6 publications, 12.77%
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American Chemical Society (ACS)
4 publications, 8.51%
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American Society for Pharmacology and Experimental Therapeutics
3 publications, 6.38%
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American Association for Cancer Research (AACR)
3 publications, 6.38%
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 4.26%
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Springer Nature
2 publications, 4.26%
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Thieme
2 publications, 4.26%
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Mary Ann Liebert
1 publication, 2.13%
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Chemical Industry Press
1 publication, 2.13%
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Bentham Science
1 publication, 2.13%
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Spandidos Publications
1 publication, 2.13%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 2.13%
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2
4
6
8
10
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Akama T. et al. Design and Synthesis of Potent Antitumor 5,4‘-Diaminoflavone Derivatives Based on Metabolic Considerations // Journal of Medicinal Chemistry. 1997. Vol. 40. No. 12. pp. 1894-1900.
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Akama T., Ishida H., Shida Y., Kimura U., Gomi K., Saito H., Fuse E., Kobayashi S., Yoda N., Kasai M. Design and Synthesis of Potent Antitumor 5,4‘-Diaminoflavone Derivatives Based on Metabolic Considerations // Journal of Medicinal Chemistry. 1997. Vol. 40. No. 12. pp. 1894-1900.
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TY - JOUR
DO - 10.1021/jm9700326
UR - https://doi.org/10.1021/jm9700326
TI - Design and Synthesis of Potent Antitumor 5,4‘-Diaminoflavone Derivatives Based on Metabolic Considerations
T2 - Journal of Medicinal Chemistry
AU - Akama, Tsutomu
AU - Ishida, Hiroyuki
AU - Shida, Yasushi
AU - Kimura, Uichiro
AU - Gomi, Katsushige
AU - Saito, Hiromitsu
AU - Fuse, Eiichi
AU - Kobayashi, Satoshi
AU - Yoda, Nobuyuki
AU - Kasai, Masaji
PY - 1997
DA - 1997/06/01 00:00:00
PB - American Chemical Society (ACS)
SP - 1894-1900
IS - 12
VL - 40
SN - 0022-2623
SN - 1520-4804
ER -
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@article{1997_Akama,
author = {Tsutomu Akama and Hiroyuki Ishida and Yasushi Shida and Uichiro Kimura and Katsushige Gomi and Hiromitsu Saito and Eiichi Fuse and Satoshi Kobayashi and Nobuyuki Yoda and Masaji Kasai},
title = {Design and Synthesis of Potent Antitumor 5,4‘-Diaminoflavone Derivatives Based on Metabolic Considerations},
journal = {Journal of Medicinal Chemistry},
year = {1997},
volume = {40},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jm9700326},
number = {12},
pages = {1894--1900},
doi = {10.1021/jm9700326}
}
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Akama, Tsutomu, et al. “Design and Synthesis of Potent Antitumor 5,4‘-Diaminoflavone Derivatives Based on Metabolic Considerations.” Journal of Medicinal Chemistry, vol. 40, no. 12, Jun. 1997, pp. 1894-1900. https://doi.org/10.1021/jm9700326.