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N-Acylbenzenesulfonamide Dihydro-1,3,4-oxadiazole Hybrids: Seeking Selectivity toward Carbonic Anhydrase Isoforms.

ABSTRACT: A series of N-acylbenzenesulfonamide dihydro-1,3,4-oxadiazole hybrids (EMAC8000a-m) was designed and synthesized with the aim to target tumor associated carbonic anhydrase (hCA) isoforms IX and XII. Most of the compounds were selective inhibitors of the tumor associated hCA XII. Moreover, resolution of EMAC8000d racemic mixture led to the isolation of the levorotatory eutomer exhibiting an increase of hCA XII inhibition potency and selectivity with respect to hCA II. Computational studies corroborated these data. Overall our data indicate that both substitution pattern and stereochemistry of dihydro-1,3,4-oxadiazole could be considered as key factors to determine activity and selectivity toward hCA isozymes. These results can provide further indication for the design and optimization of selective hCA inhibitors.

SUBMITTER: Bianco G 

PROVIDER: S-EPMC5554910 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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<i>N</i>-Acylbenzenesulfonamide Dihydro-1,3,4-oxadiazole Hybrids: Seeking Selectivity toward Carbonic Anhydrase Isoforms.

Bianco Giulia G   Meleddu Rita R   Distinto Simona S   Cottiglia Filippo F   Gaspari Marco M   Melis Claudia C   Corona Angela A   Angius Rossella R   Angeli Andrea A   Taverna Domenico D   Alcaro Stefano S   Leitans Janis J   Kazaks Andris A   Tars Kaspars K   Supuran Claudiu T CT   Maccioni Elias E  

ACS medicinal chemistry letters 20170621 8

A series of <i>N</i>-acylbenzenesulfonamide dihydro-1,3,4-oxadiazole hybrids (<b>EMAC8000a-m</b>) was designed and synthesized with the aim to target tumor associated carbonic anhydrase (hCA) isoforms IX and XII. Most of the compounds were selective inhibitors of the tumor associated hCA XII. Moreover, resolution of <b>EMAC8000d</b> racemic mixture led to the isolation of the levorotatory eutomer exhibiting an increase of hCA XII inhibition potency and selectivity with respect to hCA II. Computa  ...[more]

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