BIOMAT Database Logo BIOMAT Database Logo

Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues. 2008

Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10000 Zagreb, Croatia.

A series of 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. Cytostatic activity evaluation of the novel compounds showed that E-isomers exhibited, in general, better cytostatic activities than the corresponding Z-isomers. E-isomer 14 exhibited the best cytostatic effect against all evaluated malignant cell lines, particularly against hepatocellular carcinoma (Hep G2, IC(50)=4.3microM). However, this compound was also cytotoxic to human normal fibroblasts (WI 38). Its Z-isomer 7 showed highly specific antiproliferative activity against Hep G2 (IC(50)=18microM) and no cytotoxicity to WI 38. Moreover, compounds 3, 4 and 14 expressed some marginal inhibitory activity against HIV-1 and HIV-2.

UI MeSH Term Description Entries
D007939 Leukemia L1210 An experimental LYMPHOCYTIC LEUKEMIA of mice. Leukemia L 1210,L 1210, Leukemia,L1210, Leukemia
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D011741 Pyrimidine Nucleosides Pyrimidines with a RIBOSE attached that can be phosphorylated to PYRIMIDINE NUCLEOTIDES. Nucleosides, Pyrimidine
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D005347 Fibroblasts Connective tissue cells which secrete an extracellular matrix rich in collagen and other macromolecules. Fibroblast
D006367 HeLa Cells The first continuously cultured human malignant CELL LINE, derived from the cervical carcinoma of Henrietta Lacks. These cells are used for, among other things, VIRUS CULTIVATION and PRECLINICAL DRUG EVALUATION assays. Cell, HeLa,Cells, HeLa,HeLa Cell
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy

Related Publications

Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
The novel unsaturated acyclic nucleoside analogues: cytostatic and antiviral activity evaluations.
January 2008, Nucleic acids symposium series (2004),
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Synthesis, X-ray crystal structural study, antiviral and cytostatic evaluations of the novel unsaturated acyclic and epoxide nucleoside analogues.
December 2006, Bioorganic & medicinal chemistry,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Novel 1,2,4-triazole and purine acyclic cyclopropane nucleoside analogues: synthesis, antiviral and cytostatic activity evaluations.
July 2011, Antiviral chemistry & chemotherapy,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Synthesis and biological effects of acyclic pyrimidine nucleoside analogues.
September 1981, Journal of medicinal chemistry,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Synthesis and antiviral activity of some acyclic and C-acyclic pyrrolo[2,3-d]pyrimidine nucleoside analogues.
August 1990, Journal of medicinal chemistry,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Anti-hepatitis B virus activity of new substituted pyrimidine acyclic nucleoside analogues.
January 2009, Zeitschrift fur Naturforschung. C, Journal of biosciences,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Synthesis, 18F-radiolabelling and biological evaluations of C-6 alkylated pyrimidine nucleoside analogues.
January 2004, Nucleosides, nucleotides & nucleic acids,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Phosphodiester amidates of unsaturated nucleoside analogues: synthesis and anti-HIV activity.
July 1997, Journal of medicinal chemistry,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
Synthesis, cytostatic activity and ADME properties of C-5 substituted and N-acyclic pyrimidine derivatives.
January 2012, Bioorganic & medicinal chemistry letters,
Tatjana Gazivoda, and Silvana Raić-Malić, and Vedran Kristafor, and Damjan Makuc, and Janez Plavec, and Sinisa Bratulić, and Sandra Kraljević-Pavelić, and Kresimir Pavelić, and Lieve Naesens, and Graciela Andrei, and Robert Snoeck, and Jan Balzarini, and Mladen Mintas
The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety: Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations.
September 2010, Bioorganic & medicinal chemistry,
Copied contents to your clipboard!