Bioorganic and Medicinal Chemistry Letters, volume 14, issue 23, pages 5781-5786
Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties.
Celine Chazalette
1
,
Bernard Masereel
2
,
Stéphanie Rolin
2
,
Anne Thiry
2
,
Andrea Scozzafava
3
,
Alessio Innocenti
3
,
2
Publication type: Journal Article
Publication date: 2004-12-01
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.7
ISSN: 0960894X, 14643405
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
A series of aromatic sulfonamides incorporating indane moieties were prepared starting from commercially available 1- and 2-indanamine, and their activity as inhibitors of two carbonic anhydrase (CA, EC 4.2.1.1) isozymes, hCA I and II was studied. The new sulfonamides incorporating acetamido, 4-chloro-benzoyl, valproyl, tetra-, and pentafluorobenzoyl moieties acted as very potent inhibitors of the slow red blood cell isozyme hCA I ( K i s in the range of 1.6–8.5 nM), which usually has a lower affinity for such inhibitors, as compared to isozyme II. Some derivatives also showed excellent hCA II inhibitory properties ( K i s in the range of 2.3–12 nM), but the anticonvulsant activity of these sulfonamides was rather low as compared to that of other sulfonamide/sulfamate CA inhibitors, such as methazolamide. Furthermore, the 2-amino/acetamido-indane-5-sulfonic acids prepared during this work also showed interesting CA inhibitory properties, with inhibition constants in the range of 43–89 nM against the two isozymes, being among the most potent sulfonic acid CA inhibitors reported so far.
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Citations by publishers
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1 publication, 3.57%
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1
2
3
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5
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7
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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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Chazalette C. et al. Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties. // Bioorganic and Medicinal Chemistry Letters. 2004. Vol. 14. No. 23. pp. 5781-5786.
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Chazalette C., Masereel B., Rolin S., Thiry A., Scozzafava A., Innocenti A., T Supuran C. Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties. // Bioorganic and Medicinal Chemistry Letters. 2004. Vol. 14. No. 23. pp. 5781-5786.
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TY - JOUR
DO - 10.1016/j.bmcl.2004.09.061
UR - https://doi.org/10.1016/j.bmcl.2004.09.061
TI - Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties.
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Chazalette, Celine
AU - Masereel, Bernard
AU - Rolin, Stéphanie
AU - Thiry, Anne
AU - Scozzafava, Andrea
AU - Innocenti, Alessio
AU - T Supuran, Claudiu
PY - 2004
DA - 2004/12/01 00:00:00
PB - Elsevier
SP - 5781-5786
IS - 23
VL - 14
SN - 0960-894X
SN - 1464-3405
ER -
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@article{2004_Chazalette,
author = {Celine Chazalette and Bernard Masereel and Stéphanie Rolin and Anne Thiry and Andrea Scozzafava and Alessio Innocenti and Claudiu T Supuran},
title = {Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties.},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2004},
volume = {14},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.bmcl.2004.09.061},
number = {23},
pages = {5781--5786},
doi = {10.1016/j.bmcl.2004.09.061}
}
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MLA
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Chazalette, Celine, et al. “Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties..” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 23, Dec. 2004, pp. 5781-5786. https://doi.org/10.1016/j.bmcl.2004.09.061.
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