Publication

Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties

Winum, JY., Dogne, JM., Casini, A., de Leval, X., Montero, JL., Scozzafava, A., Vullo, D., Innocenti, A. & Supuran, CT., 24-Mar-2005, In : Journal of Medicinal Chemistry. 48, 6, p. 2121-2125 5 p.

Research output: Contribution to journalArticleAcademicpeer-review

APA

Winum, JY., Dogne, JM., Casini, A., de Leval, X., Montero, JL., Scozzafava, A., ... Supuran, CT. (2005). Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties. Journal of Medicinal Chemistry, 48(6), 2121-2125. https://doi.org/10.1021/jm0494826

Author

Winum, JY ; Dogne, JM ; Casini, A ; de Leval, X. ; Montero, JL ; Scozzafava, A ; Vullo, D ; Innocenti, A ; Supuran, CT. / Carbonic anhydrase inhibitors : Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties. In: Journal of Medicinal Chemistry. 2005 ; Vol. 48, No. 6. pp. 2121-2125.

Harvard

Winum, JY, Dogne, JM, Casini, A, de Leval, X, Montero, JL, Scozzafava, A, Vullo, D, Innocenti, A & Supuran, CT 2005, 'Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties', Journal of Medicinal Chemistry, vol. 48, no. 6, pp. 2121-2125. https://doi.org/10.1021/jm0494826

Standard

Carbonic anhydrase inhibitors : Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties. / Winum, JY; Dogne, JM; Casini, A; de Leval, X.; Montero, JL; Scozzafava, A; Vullo, D; Innocenti, A; Supuran, CT.

In: Journal of Medicinal Chemistry, Vol. 48, No. 6, 24.03.2005, p. 2121-2125.

Research output: Contribution to journalArticleAcademicpeer-review

Vancouver

Winum JY, Dogne JM, Casini A, de Leval X, Montero JL, Scozzafava A et al. Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties. Journal of Medicinal Chemistry. 2005 Mar 24;48(6):2121-2125. https://doi.org/10.1021/jm0494826


BibTeX

@article{c4c6031c5a904d7dbbb737ff2a641eef,
title = "Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties",
abstract = "Targeting proteins overexpressed in hypoxic tumors is as an important means of controlling cancer disease. One such protein is the carbonic anhydrase (CA) isoenzyme IX, which in some types of tumors is overexpressed 150-200-fold. We report here a series of sulfonamide derivatives, prepared from 2-carbohydrazido- and 4-carbohydrazido-benzenesulfonamides, which were further derivatized by reaction with aryl isocyanates or arylsulfonyl isocyanates. Several low nanomolar CA IX inhibitors were detected in this way. SAR is discussed for the diverse types of inhibitors and their affinity for different isozymes, with the aim of obtaining isozyme-specific CA IX inhibitors, with putative applications as antitumor drugs.",
keywords = "RAY CRYSTALLOGRAPHIC STRUCTURE, PRESSURE-LOWERING AGENTS, AROMATIC/HETEROCYCLIC SULFONAMIDES, HETEROCYCLIC SULFONAMIDES, SELECTIVE INHIBITORS, TRANSMEMBRANE, ANTICANCER, ADDUCT, DERIVATIVES, THERAPY",
author = "JY Winum and JM Dogne and A Casini and {de Leval}, X. and JL Montero and A Scozzafava and D Vullo and A Innocenti and CT Supuran",
year = "2005",
month = "3",
day = "24",
doi = "10.1021/jm0494826",
language = "English",
volume = "48",
pages = "2121--2125",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "AMER CHEMICAL SOC",
number = "6",

}

RIS

TY - JOUR

T1 - Carbonic anhydrase inhibitors

T2 - Synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties

AU - Winum, JY

AU - Dogne, JM

AU - Casini, A

AU - de Leval, X.

AU - Montero, JL

AU - Scozzafava, A

AU - Vullo, D

AU - Innocenti, A

AU - Supuran, CT

PY - 2005/3/24

Y1 - 2005/3/24

N2 - Targeting proteins overexpressed in hypoxic tumors is as an important means of controlling cancer disease. One such protein is the carbonic anhydrase (CA) isoenzyme IX, which in some types of tumors is overexpressed 150-200-fold. We report here a series of sulfonamide derivatives, prepared from 2-carbohydrazido- and 4-carbohydrazido-benzenesulfonamides, which were further derivatized by reaction with aryl isocyanates or arylsulfonyl isocyanates. Several low nanomolar CA IX inhibitors were detected in this way. SAR is discussed for the diverse types of inhibitors and their affinity for different isozymes, with the aim of obtaining isozyme-specific CA IX inhibitors, with putative applications as antitumor drugs.

AB - Targeting proteins overexpressed in hypoxic tumors is as an important means of controlling cancer disease. One such protein is the carbonic anhydrase (CA) isoenzyme IX, which in some types of tumors is overexpressed 150-200-fold. We report here a series of sulfonamide derivatives, prepared from 2-carbohydrazido- and 4-carbohydrazido-benzenesulfonamides, which were further derivatized by reaction with aryl isocyanates or arylsulfonyl isocyanates. Several low nanomolar CA IX inhibitors were detected in this way. SAR is discussed for the diverse types of inhibitors and their affinity for different isozymes, with the aim of obtaining isozyme-specific CA IX inhibitors, with putative applications as antitumor drugs.

KW - RAY CRYSTALLOGRAPHIC STRUCTURE

KW - PRESSURE-LOWERING AGENTS

KW - AROMATIC/HETEROCYCLIC SULFONAMIDES

KW - HETEROCYCLIC SULFONAMIDES

KW - SELECTIVE INHIBITORS

KW - TRANSMEMBRANE

KW - ANTICANCER

KW - ADDUCT

KW - DERIVATIVES

KW - THERAPY

U2 - 10.1021/jm0494826

DO - 10.1021/jm0494826

M3 - Article

VL - 48

SP - 2121

EP - 2125

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 6

ER -

ID: 14997552