Department of Pharmacy
Library of the School of Science

2025-03-20

2025

KAIMAKI ANGELIKI

ΙΩΑΝΝΗΣ ΠΑΠΑΝΑΣΤΑΣΙΟΥ, ΑΝΑΠΛΗΡΩΤΗΣ ΚΑΘΗΓΗΤΗΣ, ΤΜΗΜΑ ΦΑΡΜΑΚΕΥΤΙΚΗΣ, ΕΚΠΑ

Σύνθεση και φαρμακολογικός έλεγχος των 1-(4-φαινυλ)αδαμαντανο- και 1-(4-φαινοξυφαινυλ)αδαμαντανο- γουανυλοϋδραζονών και θειοσεμικαρβαζονών κατά του T. Brucei.

Greek

Synthesis and pharmacological evaluation of 1-(4-phenyl)adamantane- and 1-(4-phenoxyphenyl)adamantane-guanylohydrazones and thiosemicarbazones against T. Brucei.

In the context of the current dissertation, we designed and synthesized new aromatic adamantane guanylhydrazones and thiosemicarbazones with antitrypanosomal activity. For the synthesis of 1-(4-phenyl)adamantane guanylhydrazone 6, semicarbazone 7, and thiosemicarbazone 8, the 4-(1-adamantyl)benzoic acid 3 is converted to the corresponding Weinreb amide 4, which is reduced by Lithium Diisobutyl-tert-ButoxyAluminum hydride (LDBBA) to the corresponding benzaldehyde 5. The latter is then coupled with amino guanidine bicarbonate, hydrochloric semicarbazide and thiosemicarbazide respectively, to afford the desired products 6, 7, and 8. For the synthesis of 1-(4-phenoxyphenyl)adamantane guanylhydrazones 13, 15, 17 and thiosemicarbazones 14, 16, 18, the 4-(1-adamantyl)phenol 9 is converted to the suitable 1-(4-phenoxy)benzaldehydes 10-12, which are coupled with the amino guanidine bicarbonate and the thiosemicarbazide respectively, as previously described, to yield the final products 13-18. From the pharmacological evaluation of the above compounds, the adamantane benzylidene carbazone 8 is the most active with EC50 = 0.16 μM and SI = 17 against T. brucei. These results encourage us to further investigate the structure-activity relationships.

Science

Aromatic adamantane derivatives, antitrypanosomal activity, guanylhydrazones, pharmacological evaluation, thiosemicarbazone.

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https://pergamos.lib.uoa.gr/uoa/dl/object/3475966