Charge-transfer chemistry of azithromycin, the antibiotic used worldwide to treat the coronavirus disease (COVID-19). Part III: A green protocol for facile synthesis of complexes with TCNQ, DDQ, and TFQ acceptors.

Investigating the chemical properties of molecules used to combat the COVID-19 pandemic is of vital and pressing importance. In continuation of works aimed to explore the charge-transfer chemistry of azithromycin, the antibiotic used worldwide to treat COVID-19, the disease resulting from infection with the novel SARS-CoV-2 virus, in this work, a highly efficient, simple, clean, and eco-friendly protocol was used for the facile synthesis of charge-transfer complexes (CTCs) containing azithromycin and three π-acceptors: 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), and tetrafluoro-1,4-benzoquinone (TFQ). This protocol involves grinding bulk azithromycin as the donor (D) with the investigated acceptors at a 1:1 M ratio at room temperature without any solvent. We found that this protocol is environmentally benign, avoids hazardous organic solvents, and generates the desired CTCs with excellent yield (92-95%) in a straightforward means.

Charge-transfer chemistry of azithromycin, the antibiotic used worldwide to treat the coronavirus disease (COVID-19). Part II: Complexation with several π-acceptors (PA, CLA, CHL).

Finding a vaccine or cure for the coronavirus disease (COVID-19) responsible for the worldwide pandemic and its economic, medical, and psychological burdens is one of the most pressing issues presently facing the global community. One of the current treatment protocols involves the antibiotic azithromycin (AZM) alone or in combination with other compounds. Obtaining additional insight into the charge-transfer (CT) chemistry of this antibiotic could help researchers and clinicians to improve such treatment protocols. Toward this aim, we investigated the CT interactions between AZM and three π-acceptors: picric acid (PA), chloranilic acid (CLA), and chloranil (CHL) in MeOH solvent. AZM formed colored products at a 1:1 stoichiometry with the acceptors through intermolecular hydrogen bonding. An n â†’ π* interaction was also proposed for the AZM-CHL CT product. The synthesized CT products had markedly different morphologies from the free reactants, exhibiting a semi-crystalline structure composed of spherical particles with diameters ranging from 50 to 90 nm.

Charge-transfer chemistry of azithromycin, the antibiotic used worldwide to treat the coronavirus disease (COVID-19). Part I: Complexation with iodine in different solvents.

Around the world, the antibiotic azithromycin (AZM) is currently being used to treat the coronavirus disease (COVID-19) in conjunction with hydroxychloroquine or chloroquine. Investigating the chemical and physical properties of compounds used alone or in combination to combat the COVID-19 pandemic is of vital and pressing importance. The purpose of this study was to characterize the charge transfer (CT) complexation of AZM with iodine in four different solvents: CH2Cl2, CHCl3, CCl4, and C6H5Cl. AZM reacted with iodine at a 1:1 M ratio (AZM to I2) in the CHCl3 solvent and a 1:2 M ratio in the other three solvents, as evidenced by data obtained from an elemental analysis of the solid CT products and spectrophotometric titration and Job's continuous variation method for the soluble CT products. Data obtained from UV-visible and Raman spectroscopies indicated that AZM strongly interacted with iodine in the CH2Cl2, CCl4, and C6H5Cl solvents by a physically potent n→σ* interaction to produce a tri-iodide complex formulated as [AZM·I+]I3 -. XRD and TEM analyses revealed that, in all solvents, the AZM-I2 complex possessed an amorphous structure composed of spherical particles ranging from 80 to 110 nm that tended to aggregate into clusters. The findings described in the present study will hopefully contribute to optimizing the treatment protocols for COVID-19.