Nalidixic acid is an antibiotic from the quinolones family whose bioavailability is limited due to its low solubility. The development of complexes and bioinspired metal−organic frameworks has been explored as a way to achieve controlled drug delivery and release, and we demonstrate that they can also be used to tune drugs' physicochemical properties, such as solubility. Herein we disclose a series of complexes and frameworks of nalidixic acid and Zn. One of these frameworks duplicates the solubility of nalidixic acid, and it is stable on the shelf and to 77% room humidity. The incorporation of a second ligand into the frameworks is also presented, showing the possibility to develop extended networks with further potential applications.
The formation of hydrogen bonding networks of nalidixic acid–Cu(ii) complexes is discussed and may be a possible pathway leading to improved properties and increased efficiency of this antibiotic.
Aryl-3,4-dihydropyrimidinones (DHPM), thiazolopyrimidines and related heteroaromatic compounds are important classes of N-containing fused heterocycles widely used as key building blocks for pharmaceutical agents due to a wide range of biological activities that include antimicrobial and antitumor properties. As part of a program aimed at preparing new bioactive heterocycles, we designed and synthesized a series of thiazolopyrimidines and their 2-arylidene derivatives. The compounds were fully characterized by 1D-and 2D-NMR, high resolution ESI-MS/MS and single crystal X-ray diffraction analysis, which indicated a consistent Z configuration at the arylidene double bond. In addition, the ESI-MS fragmentation mechanisms for representatives of the DHPM, thiazolopyrimidine, and 2-arylidene-thiazolopyrimidine classes were elucidated. Studies are underway to assess the biological activities of the new compounds.
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