Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids
Тип публикации: Journal Article
Дата публикации: 2020-03-05
scimago Q1
wos Q1
БС1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
32134263
Drug Discovery
Molecular Medicine
Краткое описание
Semisynthetic artemisinins and other bioactive peroxides are best known for their powerful antimalarial activities, and they also show substantial activity against schistosomes-another hemoglobin-degrading pathogen. Building on this discovery, we now describe the initial structure-activity relationship (SAR) of antischistosomal ozonide carboxylic acids OZ418 (2) and OZ165 (3). Irrespective of lipophilicity, these ozonide weak acids have relatively low aqueous solubilities and high protein binding values. Ozonides with para-substituted carboxymethoxy and N-benzylglycine substituents had high antischistosomal efficacies. It was possible to increase solubility, decrease protein binding, and maintain the high antischistosomal activity in mice infected with juvenile and adult Schistosoma mansoni by incorporating a weak base functional group in these compounds. In some cases, adding polar functional groups and heteroatoms to the spiroadamantane substructure increased the solubility and metabolic stability, but in all cases decreased the antischistosomal activity.
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ГОСТ
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Wu J. et al. Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids // Journal of Medicinal Chemistry. 2020. Vol. 63. No. 7. pp. 3723-3736.
ГОСТ со всеми авторами (до 50)
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Wu J., Wang X., Chiu F. C., Häberli C., Shackleford D., Ryan E., Sriraghavan K., Bulbule V. J., Wallick A. I., Dong Y., WHITE K. E., Davis P. H., Charman S. C., Keiser J., Vennerstrom J. L. Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids // Journal of Medicinal Chemistry. 2020. Vol. 63. No. 7. pp. 3723-3736.
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TY - JOUR
DO - 10.1021/acs.jmedchem.0c00069
UR - https://doi.org/10.1021/acs.jmedchem.0c00069
TI - Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids
T2 - Journal of Medicinal Chemistry
AU - Wu, Jianbo
AU - Wang, Xiaofang
AU - Chiu, Francis C.K.
AU - Häberli, Cécile
AU - Shackleford, D.
AU - Ryan, Eileen
AU - Sriraghavan, Kamaraj
AU - Bulbule, Vivek J
AU - Wallick, Alexander I
AU - Dong, Yuxiang
AU - WHITE, KAREN E.
AU - Davis, Paul H
AU - Charman, Susan C
AU - Keiser, J
AU - Vennerstrom, Jonathan L.
PY - 2020
DA - 2020/03/05
PB - American Chemical Society (ACS)
SP - 3723-3736
IS - 7
VL - 63
PMID - 32134263
SN - 0022-2623
SN - 1520-4804
ER -
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BibTex (до 50 авторов)
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@article{2020_Wu,
author = {Jianbo Wu and Xiaofang Wang and Francis C.K. Chiu and Cécile Häberli and D. Shackleford and Eileen Ryan and Kamaraj Sriraghavan and Vivek J Bulbule and Alexander I Wallick and Yuxiang Dong and KAREN E. WHITE and Paul H Davis and Susan C Charman and J Keiser and Jonathan L. Vennerstrom},
title = {Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids},
journal = {Journal of Medicinal Chemistry},
year = {2020},
volume = {63},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.jmedchem.0c00069},
number = {7},
pages = {3723--3736},
doi = {10.1021/acs.jmedchem.0c00069}
}
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MLA
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Wu, Jianbo, et al. “Structure–Activity Relationship of Antischistosomal Ozonide Carboxylic Acids.” Journal of Medicinal Chemistry, vol. 63, no. 7, Mar. 2020, pp. 3723-3736. https://doi.org/10.1021/acs.jmedchem.0c00069.