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Autori: Gazivoda, Tatjana; Raić-Malić, Silvana; Kraljević-Pavelić, Sandra; Pavelić, Krešimir; Balzarini, Jan; Mintas, Mladen
Naslov: The New Unsaturated Acyclic C-5 Pyrimidine Nucleoside Analogues: Synthesis, Cytostatic And Anti-Hiv Evaluations
Izvornik: Ninth Tetrahedron Symposium: Challenges in Organic and Bioorganic Chemistry / Martin, Stephen (ur.). - Berkeley : Elsevier , 2008. P1.98-P1.99.
Skup: Ninth Tetrahedron Symposium: Challenges in Organic and Bioorganic Chemistry
Mjesto i datum: Berkeley, SAD, 22-25.07.2008.
Ključne riječi: unsaturated acyclic C-5 pyrimidine nucleoside analogues; cytostatic evaluations; anti-HIV activities
Sažetak:
Many nucleoside analogues with interesting biological properties have arisen by substitution at the 5-position of the uracil base in the 2'-deoxyuridine series.[1] Pyrimidine nucleosides containing C-5 alkynyl groups have been shown to possess significant antiviral and/or anticancer properties.[2] We have reported that some pyrimidines and purines containing gama-(Z)-ethylidene-2, 3-dibenzylbutenolide exhibited antiproliferative effects against malignant human tumor cell lines.[3] We have also reported that the (Z)-4-amino-2-butenyladenine nucleoside analogue showed selective activity against HIV-1.[4] The novel C-5 alkynyl pyrimidine nucleoside analogues (1-14) in which the sugar moiety was replaced by the conformationally restricted Z- and E-2-butenyl spacer between the phthalimido and pyrimidine ring were synthesized by using Sonogashira cross-coupling reaction (Scheme). Scheme: (i) NaH, DMF, argon atmosphere, r.t. ; (ii) R-C≡ CH, iPr2EtN, (PPh3)4Pd, CuI, DMF, r.t. The compounds 1-14 were evaluated for their cytostatic activities against malignant human tumor cell lines: murine leukemia (L1210), human T-lymphocyte (Molt4/C8 and CEM), cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), colorectal adenocarcinoma (SW 620), breast epithelial adenocarcinoma (MCF-7), hepatocellular carcinoma (Hep G2) and normal diploid human fibroblasts (WI 38), as well as for their inhibitory activities against HIV-1 and HIV-2 in human T-lymphocyte (CEM) cells. Compounds 3 and 4 showed some specific albeit slight activity against HIV-1 (3: EC50= 35 uM, 4: EC50= 10 uM), while compound 14 exhibited moderate activity against both HIV-1 (EC50= 14 uM) and HIV-2 (EC50= 3.1 uM). Cytostatic activity evaluation of the novel compounds showed that E-isomers (8-14) exhibited better cytostatic activities than the corresponding Z-isomers (1-7). REFERENCES 1. De Clercq, E. Nucleosides Nucleotides 1987, 6, 197. 2. Herdewijn, P. Antiviral Chem. Chemother. 1994, 5, 131 ; Beres, J., Bentrude, W.G., Balzarini, J., De Clercq, E., Otvos, L. J. Med. Chem. 1986, 29, 494. 3. Raić-Malić, S., Nagl, A., Pavelić, K., De Clercq, E., Mintas, M. J. Med. Chem. 1999, 42, 2673 ; ibid. J. Med. Chem. 2000, 43, 4806 ; Gazivoda, T., Plavec, J., Kraljević, S., Kralj, M., Pavelić, K. ; Balzarini, J., De Clercq, E., Mintas, M., Raić-Malić, S. Bioorg. Med. Chem. 2005, 13, 131 ; ibid. J. Med. Chem. 2007, 50, 4105 ; ibid. Bioorg. Med. Chem. 2007, 15, 749. 4. Krištafor, V., Raić-Malić, S., Pavelić, K., Balzarini, J., De Clercq, E. Bioorg. Med. Chem. 2006, 14, 8126
Vrsta sudjelovanja: Poster
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Međunarodna recenzija
Projekt / tema: 125-0982464-2925, 125-0982464-2922, 098-0982464-2393
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Temeljne medicinske znanosti
Upisao u CROSBI: sraic@fkit.hr (sraic@fkit.hr), 31. Srp. 2008. u 11:39 sati



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