By chance, not design : a new furosemide derivative from zinc(ii) complex studies

Podjed Rihtaršič, Nina (avtor), Cerc Korošec, Romana (avtor), Modec, Barbara (avtor)

Furosemide, a sulfonamide-based diuretic, may also be of interest as a ligand capable of binding to metal ions. Our studies of zinc(II) coordination chemistry with furosemide in organic solvents resulted in a crystalline precipitate. Initial characterization was challenging because single crystals were of insufficient quality for an unambiguous structural determination. X-ray analysis confirmed a four-coordinate zinc(II) complex with two deprotonated furosemides (fur$^–$) bound in a monodentate manner and two simple monodentate ligands. Complementary techniques, i.e., infrared spectroscopy, NMR spectroscopy, and thermal analysis, revealed their identity as ammonia, generated in situ from acetonitrile hydrolysis. The composition of the product is thus [Zn(fur)$_2$(NH$_3$)$_2$]·(CH$_3$CH$_2$)$_2$O (1). Although our attempt to prepare better-diffracting crystals was unsuccessful, it led to the serendipitous discovery of a new furosemide derivative, labeled 2. The derivative features two structural modifications compared to the parent furosemide, namely, ester and amidine functionalities. Single-crystal analysis of 2 showed the esterification of the carboxyl group with methanol and nucleophilic addition of the sulfonamide NH$_2$ group to the triple bond of acetonitrile, used as a solvent. These results expand the structural chemistry of furosemide and demonstrate its capacity to undergo unprecedented transformations in zinc(II)-mediated systems.

• Jezik: Angleški jezik
• Ključne besede: furosemide, amidine, zinc(II), coordination chemistry, crystal structure
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2026
• Št. strani: Str. 10614-10619
• Številčenje: Vol. 11, iss. 6
• PID: 20.500.12556/RUL-179665
• UDK: 546.47
• ISSN pri članku: 2470-1343
• DOI: 10.1021/acsomega.5c12211
• COBISS.SI-ID: 268883459
• Datum objave v RUL: 19.02.2026

Gradivo je del revije

• Naslov: ACS omega
• Skrajšan naslov: ACS omega
• Založnik: American Chemical Society
• ISSN: 2470-1343
• COBISS.SI-ID: 525873945

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: furosemid, amidin, cink(II), koordinacijska kemija, kristalna struktura

Projekti

• Financer: ARIS - Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije
• Številka projekta: P1-0134-2022
• Naslov: Kemija za trajnostni razvoj

• Financer: ARIS - Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije
• Številka projekta: I0-0022-2022
• Naslov: Mreža raziskovalnih infrastrukturnih centrov Univerze v Ljubljani (MRIC UL)