Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation.

ABSTRACT: A series of bio-organometallic-hydrazones of the general formula [{(η⁵-C₅H₄)-C(R)=N-N(H)-C₆H₄-4-SO₂NH₂}]MLn(MLn = Re(CO)₃, Mn(CO)₃, FeCp; R=H, CH₃) were prepared by reaction of formyl/acetyl organometallic precursors with 4-hydrazino-benzenesulphonamide. All compounds were characterized by conventional spectroscopic techniques (infra-red, ¹H and ¹³C NMR, mass spectrometry and elemental analysis). Biological evaluation as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors agents was carried out using four human/h) isoforms, hCA I, II, IX and XII. The cytosolic isoforms hCA I and II were effectively inhibited by almost all derivatives with inhibition constants of 1.7-22.4 nM. Similar effects were observed for the tumour-associated transmembrane isoform hCA XII (K_Is of 1.9-24.4 nM). hCA IX was less sensitive to inhibition with these compounds. The presence of bio-organometallic or metallo-carbonyl moieties in the molecules of these CAIs makes them amenable for interesting pharmacologic applications, for example for compounds with CO donating properties.

SUBMITTER: Brichet J 

PROVIDER: S-EPMC7034112 | biostudies-literature |

REPOSITORIES: biostudies-literature