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Pregled bibliografske jedinice broj: 369102

The novel primaquine derivatives of N-alkyl, cycloalkyl or aryl urea: synthesis, cytostatic and antiviral activity evaluations


Džimbeg, Gabrijela; Rajić, Zrinka; Zorc, Branka; Kralj, Marijeta; Ester, Katja; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen
The novel primaquine derivatives of N-alkyl, cycloalkyl or aryl urea: synthesis, cytostatic and antiviral activity evaluations // Abstracts of the 3rd Pharmaceutical Sciences World Congress
Amsterdam, Nizozemska, 2007. (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
The novel primaquine derivatives of N-alkyl, cycloalkyl or aryl urea: synthesis, cytostatic and antiviral activity evaluations

Autori
Džimbeg, Gabrijela ; Rajić, Zrinka ; Zorc, Branka ; Kralj, Marijeta ; Ester, Katja ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Abstracts of the 3rd Pharmaceutical Sciences World Congress / - , 2007

Skup
Pharmaceutical Sciences World Congress (3 ; 2007)

Mjesto i datum
Amsterdam, Nizozemska, 22-25.04.2007

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Primaquine; malaria; urea; cytostatic activity

Sažetak
Primaquine, N4-(6-methoxy-8-quinolinyl)-1, 4-pentanediamine, is known antimalarial drug that is active against both the latent liver forms of the relapsing malaria caused by Plasmodium vivax and Plasmodium ovale and the gametocytes from all species of parasite causing human malaria, including chloroquine-resistant Plasmodium falciparum. The novel urea primaquine derivatives 3a-i were prepared by aminolysis of benzotriazolide 2 with the corresponding amine in the presence or absence of triethylamine. In order to obtain the targeted derivatives of urea 3a-i with different lipophilicity, various aliphatic and aromatic primary or secondary amines were used for their synthesis (diethylamine, cyclopentylamine, cyclohexylamine, cyclohexanemethylamine, dicyclohexylamine, 2-phenylethylamine, 4-(aminomethyl)pyridine and benzhydrylamine). Compound 2 was prepared by acylation of primaquine with 1-benzotriazole carboxylic acid chloride. Among all compounds evaluated, the pyridine derivative 3h exhibited the best cytostatic activities against colon carcinoma, human T-lymphocyte and murine leukemia. However, this compound showed also rather marked cytotoxicity towards human normal fibroblasts. The highest selectivity in the inhibitory effects on human malignant tumour cell lines vs. normal fibroblasts was found for ureas 3c, 3d and 3g. Results of broad antiviral evaluation showed that pyridine and phenethyl derivatives of urea 3h and 3g exhibited some selective inhibition against cytomegalovirus.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti, Farmacija



POVEZANOST RADA


Projekt / tema
006-0000000-3216 - Sinteza, karakterizacija i djelovanje potencijalnih i poznatih ljekovitih tvari (Branka Zorc, )
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Krešimir Pavelić, )
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mladen Mintas, )

Ustanove
Farmaceutsko-biokemijski fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb