Journal of Medicinal Chemistry, volume 34, issue 3, pages 1142-1154
Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship
Publication type: Journal Article
Publication date: 1991-03-01
Journal:
Journal of Medicinal Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 7.3
ISSN: 00222623, 15204804
Drug Discovery
Molecular Medicine
Abstract
A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and N1 (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substituents.
Top-30
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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1 publication, 2.44%
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Citations by publishers
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Elsevier
16 publications, 39.02%
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Wiley
8 publications, 19.51%
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Springer Nature
4 publications, 9.76%
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American Chemical Society (ACS)
2 publications, 4.88%
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Taylor & Francis
2 publications, 4.88%
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The Chemical Society of Japan
2 publications, 4.88%
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Royal Society of Chemistry (RSC)
1 publication, 2.44%
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Thieme
1 publication, 2.44%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 2.44%
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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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Domagala J. M. et al. Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship // Journal of Medicinal Chemistry. 1991. Vol. 34. No. 3. pp. 1142-1154.
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Domagala J. M., Bridges A. J., Culbertson T. P., Gambino L., Hagen S. E., Karrick G., Porter K., Sanchez J. P., Sesnie J. A. Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship // Journal of Medicinal Chemistry. 1991. Vol. 34. No. 3. pp. 1142-1154.
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TY - JOUR
DO - 10.1021/jm00107a039
UR - https://doi.org/10.1021/jm00107a039
TI - Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship
T2 - Journal of Medicinal Chemistry
AU - Domagala, John M.
AU - Bridges, Alex J.
AU - Culbertson, Townley P
AU - Gambino, Laura
AU - Hagen, Susan E
AU - Karrick, Gregory
AU - Porter, Kenneth
AU - Sanchez, Joseph P.
AU - Sesnie, Josephine A
PY - 1991
DA - 1991/03/01 00:00:00
PB - American Chemical Society (ACS)
SP - 1142-1154
IS - 3
VL - 34
SN - 0022-2623
SN - 1520-4804
ER -
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@article{1991_Domagala,
author = {John M. Domagala and Alex J. Bridges and Townley P Culbertson and Laura Gambino and Susan E Hagen and Gregory Karrick and Kenneth Porter and Joseph P. Sanchez and Josephine A Sesnie},
title = {Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship},
journal = {Journal of Medicinal Chemistry},
year = {1991},
volume = {34},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jm00107a039},
number = {3},
pages = {1142--1154},
doi = {10.1021/jm00107a039}
}
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Domagala, John M., et al. “Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship.” Journal of Medicinal Chemistry, vol. 34, no. 3, Mar. 1991, pp. 1142-1154. https://doi.org/10.1021/jm00107a039.