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Heterocyclic periphery in the design of carbonic anhydrase inhibitors : 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms. / Krasavin, Mikhail; Shetnev, Anton; Sharonova, Tatyana; Baykov, Sergey; Tuccinardi, Tiziano; Kalinin, Stanislav; Angeli, Andrea; Supuran, Claudiu T.

In: Bioorganic Chemistry, Vol. 76, 01.02.2018, p. 88-97.

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

Harvard

Krasavin, M, Shetnev, A, Sharonova, T, Baykov, S, Tuccinardi, T, Kalinin, S, Angeli, A & Supuran, CT 2018, 'Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms', Bioorganic Chemistry, vol. 76, pp. 88-97. https://doi.org/10.1016/j.bioorg.2017.10.005

APA

Krasavin, M., Shetnev, A., Sharonova, T., Baykov, S., Tuccinardi, T., Kalinin, S., Angeli, A., & Supuran, C. T. (2018). Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms. Bioorganic Chemistry, 76, 88-97. https://doi.org/10.1016/j.bioorg.2017.10.005

Vancouver

Krasavin M, Shetnev A, Sharonova T, Baykov S, Tuccinardi T, Kalinin S et al. Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms. Bioorganic Chemistry. 2018 Feb 1;76:88-97. https://doi.org/10.1016/j.bioorg.2017.10.005

Author

Krasavin, Mikhail ; Shetnev, Anton ; Sharonova, Tatyana ; Baykov, Sergey ; Tuccinardi, Tiziano ; Kalinin, Stanislav ; Angeli, Andrea ; Supuran, Claudiu T. / Heterocyclic periphery in the design of carbonic anhydrase inhibitors : 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms. In: Bioorganic Chemistry. 2018 ; Vol. 76. pp. 88-97.

BibTeX

@article{25d4e63e96b340ccbb3ef9f68cb32d8f,
title = "Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms",
abstract = "A series of novel aromatic primary sulfonamides decorated with diversely substituted 1,2,4-oxadiazole periphery groups has been prepared using a parallel chemistry approach. The compounds displayed a potent inhibition of cytosolic hCA II and membrane-bound hCA IX isoforms. Due to a different cellular localization of the two target enzymes, the compounds can be viewed as selective inhibition tools for either isoform, depending on the cellular permeability profile. The SAR findings revealed in this study has been well rationalized by docking simulation of the key compounds against the crystal structures of the relevant hCA isoforms.",
keywords = "1,2,4-Oxadiazole, Acylation, Carbonic anhydrase, Cyclodehydration, Isoform-selective inhibitors, Nanomolar inhibition, Periphery groups, Primary sulfonamides, Superbase, CRYSTAL-STRUCTURE, SULFONAMIDES, ACTIVATORS, SULFOCHLORINATION, ASTROCYTES, DISCOVERY, THERAPEUTIC APPLICATIONS, PROFILE, PICOMOLAR INHIBITORS, AGENTS",
author = "Mikhail Krasavin and Anton Shetnev and Tatyana Sharonova and Sergey Baykov and Tiziano Tuccinardi and Stanislav Kalinin and Andrea Angeli and Supuran, {Claudiu T.}",
year = "2018",
month = feb,
day = "1",
doi = "10.1016/j.bioorg.2017.10.005",
language = "English",
volume = "76",
pages = "88--97",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Heterocyclic periphery in the design of carbonic anhydrase inhibitors

T2 - 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms

AU - Krasavin, Mikhail

AU - Shetnev, Anton

AU - Sharonova, Tatyana

AU - Baykov, Sergey

AU - Tuccinardi, Tiziano

AU - Kalinin, Stanislav

AU - Angeli, Andrea

AU - Supuran, Claudiu T.

PY - 2018/2/1

Y1 - 2018/2/1

N2 - A series of novel aromatic primary sulfonamides decorated with diversely substituted 1,2,4-oxadiazole periphery groups has been prepared using a parallel chemistry approach. The compounds displayed a potent inhibition of cytosolic hCA II and membrane-bound hCA IX isoforms. Due to a different cellular localization of the two target enzymes, the compounds can be viewed as selective inhibition tools for either isoform, depending on the cellular permeability profile. The SAR findings revealed in this study has been well rationalized by docking simulation of the key compounds against the crystal structures of the relevant hCA isoforms.

AB - A series of novel aromatic primary sulfonamides decorated with diversely substituted 1,2,4-oxadiazole periphery groups has been prepared using a parallel chemistry approach. The compounds displayed a potent inhibition of cytosolic hCA II and membrane-bound hCA IX isoforms. Due to a different cellular localization of the two target enzymes, the compounds can be viewed as selective inhibition tools for either isoform, depending on the cellular permeability profile. The SAR findings revealed in this study has been well rationalized by docking simulation of the key compounds against the crystal structures of the relevant hCA isoforms.

KW - 1,2,4-Oxadiazole

KW - Acylation

KW - Carbonic anhydrase

KW - Cyclodehydration

KW - Isoform-selective inhibitors

KW - Nanomolar inhibition

KW - Periphery groups

KW - Primary sulfonamides

KW - Superbase

KW - CRYSTAL-STRUCTURE

KW - SULFONAMIDES

KW - ACTIVATORS

KW - SULFOCHLORINATION

KW - ASTROCYTES

KW - DISCOVERY

KW - THERAPEUTIC APPLICATIONS

KW - PROFILE

KW - PICOMOLAR INHIBITORS

KW - AGENTS

UR - http://www.scopus.com/inward/record.url?scp=85034047049&partnerID=8YFLogxK

U2 - 10.1016/j.bioorg.2017.10.005

DO - 10.1016/j.bioorg.2017.10.005

M3 - Article

AN - SCOPUS:85034047049

VL - 76

SP - 88

EP - 97

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

ER -

ID: 34632614