Water-bridged tetrameric supramolecular synthons in a novel tetrasubstituted imidazole–phenylalanine derivative synthesized via a Debus–Radziszewski reaction

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Leishmaniasis remains a significant global health challenge, as current treatments rely on antimonial compounds that are increasingly limited by toxicity, high costs and emerging drug resistance. In this study, we report the synthesis of a novel 1,2,4,5-tetrasubstituted 1 H -imidazole derivative, namely, (2 S )-2-[2-(4-nitrophenyl)-4,5-diphenyl-1 H -imidazol-1-yl]-3-phenylpropanoic acid monohydrate, C 30 H 23 N 3 O 4 ·H 2 O, via a Debus–Radziszewski multicomponent reaction using phenylalanine as a chiral precursor. The compound was obtained in 55% yield and its structure was unequivocally characterized by 1 H NMR and FT–IR spectroscopy, and high-resolution mass spectrometry (HRMS). Single-crystal X-ray diffraction analysis revealed an atypical supramolecular architecture defined by a tetrameric synthon. This assembly is orchestrated by two water molecules acting as multidirectional bridges through an intricate hydrogen-bonding network involving the carboxyl groups and pyridinic N atoms. The resulting 3D framework features continuous polar channels and confirms the full retention of the absolute L-configuration of the phenylalanine moiety. These findings highlight the potential of amino acid-functionalized imidazoles as versatile scaffolds for the development of targeted antileishmanial agents.

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