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Synthesis of Semicarbazide, Semicarbazone and Urea Derivatives of Primaquine (CROSBI ID 616004)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Perković, Ivana ; Pavić, Kristina ; Zorc, Branka Synthesis of Semicarbazide, Semicarbazone and Urea Derivatives of Primaquine // EFMC International Symposium on Medicinal Chemistry / Tarzia, Giorgio ; Metternich, Rainer (ur.). Lisabon: Wiley-VCH, 2014. str. 388-388

Podaci o odgovornosti

Perković, Ivana ; Pavić, Kristina ; Zorc, Branka

engleski

Synthesis of Semicarbazide, Semicarbazone and Urea Derivatives of Primaquine

Primaquine (PQ), the 8-aminoquinoline derivative is an antimalarial drug active against various forms of Plasmodium species. A major drawback of primaquine are the high risk of methemoglobinemia, relatively low therapeutic index and rapid metabolisation to carboxyprimaquine, which is less active than the drug. Many attempts have been made to prepare primaquine derivatives in the search for compounds with higher bioavailability (1). Compounds with substituted terminal primary amine in primaquine have shown some new biological activity other than antimalarial (2- 4). In our recent work we have shown that the compounds bearing benzhydryl and benzyl moieties at the position 4 of the 1, 4- substituted primaquine semicarbazides showed significant cytostatic activity in low micromolar concentrations towards various carcinoma cell lines (3). Semicarbazides and semicarbazones are well known class of compounds with different biological acitivities (5). The aim of our research was to prepare semicarbazide/semicarbazone/urea primaquine derivatives bearing various benzhydryl and phenyl moieties at the one and primaquine moiety at the other end. Compounds 3c and 6c were obtained in the reaction of primaquine (PQ) or primaquine semicarbazide 5 and 4- chloro-3- (fluoromethyl)phenyl isocyanate. Compounds 3a, b and 6a, b were obtained in the reaction of primaquine (PQ) or primaquine semicarbazide 5 and corresponding active ureas (2a, b). The starting compound benzotriazole carboxylic acid chloride (1) was used for the preparation of both active ureas 2a, b and benzotriazolide 4. Compound 4 with hydrazine hydrate gave primaquine semicarbazide 5. Structures of newly prepared primaquine derivatives were confirmed by IR, 1H and 13C NMR and MS spectroscopy. Evaluation of their biological activity is in progress.

primaquine; derivatives; synthesis

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Podaci o prilogu

388-388.

2014.

objavljeno

Podaci o matičnoj publikaciji

EFMC International Symposium on Medicinal Chemistry

Tarzia, Giorgio ; Metternich, Rainer

Lisabon: Wiley-VCH

Podaci o skupu

EFMC International Symposium on Medicinal Chemistry

poster

07.09.2014-11.09.2014

Lisabon, Portugal

Povezanost rada

Kemija, Farmacija