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1.
Ludovic Colombeau Karine Teste Amel Hadj-Bouazza Vincent Chaleix Rachida Zerrouki Michel Kraemer 《Nucleosides, nucleotides & nucleic acids》2013,32(2):110-120
The synthesis and biological activity of chloroethyl pyrimidine nucleosides is presented. One of these new nucleosides analogues significantly inhibited cell proliferation, migration and invasion as tested in vitro on the A431 vulvar epidermal carcinoma cell line. 相似文献
2.
Wael A. El-Sayed Aymn E. Rashad Samir M. Awad Mamdouh M. Ali 《Nucleosides, nucleotides & nucleic acids》2013,32(4):261-274
Some new thiopyrimidine acyclic nucleosides and thioglycoside derivatives 3a-c, 4a-c, 6a,b, and 7a,b were synthesized. The cytotoxicity and antitumor evaluation of all prepared compounds have been tested in vitro against Ehrlich's ascites carcinoma cell line and their activity against glutathione peroxidase and catalase were reported. The role of the prepared compounds as free radical regulators and the therapeutic antitumor effect of a balanced generation of free radicals are discussed. Compounds 2, 3b, 3c, 4a, and 4c inhibited significantly in a dose dependent manner the growth of Ehrlich ascites carcinoma cells while the other compounds did not show any antitumor activity even at higher concentrations. 相似文献
3.
Zygmunt Kazimierczuk Harri Lönnberg Juhani Vilpo Wolfgang Pfleiderer 《Nucleosides, nucleotides & nucleic acids》2013,32(4):599-617
Abstract Various new haloindazole-1-β-D-ribofuranosides (10-17,20,21) and a 2-β-D-ribofuranoside (18) have been synthesized by the fusion method and by direct halogenations, respectively. The new nucleosides have been characterized by UV and 1H NMR spectra as well as pKa determinations. Indazole ribofuranosides behave in aqueous acid like purine and benzimidazole nucleosides showing the same mechanism of cleavage of the glycosidic bonds. Toxicity studies against various cell populations indicate only little biological activities. 相似文献
4.
M. Bretner M. Balinska K. Krawiec B. Kierdaszuk D. Shugar T. Kulikowski 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):657-660
Abstract Two pathways are described for the synthesis of the 2′-deoxynucleosides of 2-thiocytosine and 5-fluoro-2-thiocytosine: (a) by nucleoside condensation, (b) by amination of the corresponding nucleosides of 2,4-dithiouracil. Biological activities vs two cell systems are described. The nucleosides are moderate to weak substrates of deoxycytidine kinase and, partly as a result of this, reasonable good inhibitors of the enzyme 相似文献
5.
Galal E. H. Elgemeie Adel M. E. Attia Sherifa S. Alkabai 《Nucleosides, nucleotides & nucleic acids》2013,32(4):723-733
Abstract A novel synthesis of condensed bicyclic thiopyrimidine glycosides utilising 1H-cyclopentapyrimidine-2(3H)-thiones and α-bromoglucose or α-bromogalactose tetraacetate as starting components is described. 相似文献
6.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):813-815
Abstract Synthesis and biological activity of 7- and 9-isomers (Z+E) of methylenecyclopropane analogues of 2-aminopurine nucleosides is described. The (S,Z)-9-isomer is a substrate for xanthine oxidase. 相似文献
7.
Lea Messini Kamal N. Tiwari John A. Montgomery John A. Secrist III 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):683-685
Abstract Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-d-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9α and 9β anomers as major products. These anomers were separated and converted to 2′-deoxy-4′-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their α-anomers. 相似文献
8.
Michael E. Jung Christopher J. Nichols Oliver Kretschik Yue Xu 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):541-546
Abstract New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-c and the L-2′,3′-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4. 相似文献
9.
Abstract Purine analogues and derivatives exhibit a broad range of pharmacological activities and are used in the chemotherapy of cancer, parasitic and viral infections, and for the suppression of immune responses. Undoubtedly, this wide range of biological activities reflect an equally wide number of biochemical sites of action, one of which is the purine de novo pathway. New agents which can either serve as inhibitors of enzymes involved in this pathway or as substrates are continually sought. The unique series of nucleosides described herein should meet these desired needs. The synthesis of 1involved glycosylation of a suitably 4,5-disubstituted imidazole and subsequent cyclization of the imidazole nucleoside so formed to the imidazo[4,5-d]pyridazine nucleoside. Such methodology was successfully employed1,2 in the preparation of certain 4,7-disubstituted imidazo[4,5-d]pyridazine nucleosides. Chlorination of 1furnished 4-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribo-furanosyl)imidazo[4,5-dlpyridazine (2) in 80% yield. This versatile intermediate can now serve as a precursor to a variety of 4-substituted imidazo[4,5-d]pyridazine nucleosides. 相似文献
10.
Bozenna Golankiewicz Joanna Zeidler Erik De Clercq 《Nucleosides, nucleotides & nucleic acids》2013,32(4):663-678
Abstract C-acyclic nucleoside analogues of inosine and guanosine 8-[(RS)-2,3-dihydroxypropyl] imidazo [1,5-a]-1,3,5-triazin-4 (3H)-ones 6a, c, d were synthesized. The route involved the cyclization-rearrangement of 5-acylamino-5-allyl-6-amino-4,5-dihydropyrimidin-4-ones 4a-c to 8-allylimidazo [1,5-a]-1,3,5-triazin-4 (3H) ones 5a-c. 5a was transformed selectively into 5d by reductive desulfurization with highly deactivated Raney nickel. The poorly soluble compounds 5b and 5c were converted to N-2-acetylated 5f and 5g. Osmium tetroxide hydroxylation of 5d, f, g gave 6a, c, d. None of the newly synthesized C-acyclic nucleoside derivatives showed an appreciable antiviral or antitumor cell activity. 相似文献
11.
Toshiaki Waga Hiroshi Ohrui Hiroshi Meguro 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):287-304
Abstract A series of 2′-deoxy, 2′,3′-unsaturdted and 2′,3′-dideoxynucleoside analogues, which have an additional methyl group at the 4′-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2′-deoxy-4′-C-methyl nucleosides exhibited potent activity. 相似文献
12.
Yuichi Yoshimura Fumitaka Kano Shuichi Miyazaki Noriyuki Ashida Shinji Sakata Kazuhiro Haraguchi 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):305-324
Abstract 2′-Deoxy-, 2′-bromo-, and arabino-1′-C-cyano-pyrimidine nucleosides were synthesized from O2 ,2′-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1′,2′-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed. 相似文献
13.
Isabel Nieto M. José Figueira J. Manuel Blanco Olga Caamaño Franco Fernández Erik De Clercq 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):641-642
Abstract New carbocyclic nucleosides with purine (compounds 2a-2c), 8-azapurine (compounds 2d and 2e) or pyrimidine (compound 3) as base were prepared and assayed for in vitro activity. 相似文献
14.
Galal E. H. Elgemeie Omar A. Mansour Nadia H. Metwally 《Nucleosides, nucleotides & nucleic acids》2013,32(1):113-123
Abstract A series of different novel nonclassical nucleosides have been synthesised and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. 相似文献
15.
Arun P. Sharma Abraham P. Ollapally Willishea Jones Tracey Lemon 《Nucleosides, nucleotides & nucleic acids》2013,32(5):1009-1038
Abstract Synthesis of unsaturated ketohexopyranosyl nucleosides of a few pyrimidines is described. The results of their bioevaluation for anticancer and antiviral activity are also discussed. 相似文献
16.
Lina Lin Jia Sheng Razin K. Momin Quan Du Zhen Huang 《Nucleosides, nucleotides & nucleic acids》2013,32(1):56-66
Many organic compounds containing selenium have shown anticancer effects and some have been used in chemoprevention of cancers and other diseases. Though Se-containing amino acids are generally used for these purposes, the natural nucleosides may also be used as Se-carriers for these important applications. Therefore, we describe here the convenient synthesis of the new 3′-MeSe-thymidine nucleoside and the other uridine and thymidine derivatives modified with MeSe at the 2′ and 5′ positions, and report their anti-tumor activity against prostate cancer cell lines. Our work demonstrates for the first time anticancer activity of the methylseleno nucleosides. 相似文献
17.
Bernard L. Flynn Vilma Macolino Geoffrey T. Crisp 《Nucleosides, nucleotides & nucleic acids》2013,32(4):763-779
Abstract Coupling of suitably protected 5-iodouridine or 5-iodo-2′-deoxyuridine with either arylboronic acids or aryltrimethylstannanes in the presence of a palladium catalyst gave moderate yields of the corresponding 5-aryluridines and 5-aryC2′-deoxyuridines. 5-Hydroxyuridine was converted into 5-(trifluoromethanesulphonyl)uridine in good yield and the triacetate of this modified nucleoside also underwent palladium-catalysed couplings with a variety of organostannanes to produce the 5-substituted uridine in excellent yield. 相似文献
18.
Ibrahim A. I. Ali Iman A. Al-Masoudi Nazik M. Aziz Najim A. Al-Masoudi 《Nucleosides, nucleotides & nucleic acids》2013,32(2):146-156
A series of acyclonucleosides substituted 1-(4,5-dihydroxypentyl) (13-8) and 2-(4,5-dihydroxypentyloxy)quinoxalines (19-24) were synthesized by the sharpless asymmetric dihydroxylation of the derivatives 1-6 and 7-12, respectively. Treatment of the quinoxaline base 26 with (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl-p-toluenesulfonate (27) in the presence of NaH/DMF furnished 28. Acid hydrolysis of 28 gave 1-(2,3-dihydroxypropyl)-6,7-dimethyl-quinoxaline-2-one (29). Alternatively, 29 was prepared by sharpless dihydroxylation of 30. All the compounds were evaluated for their in vitro anti-HIV-1 and HIV-2 in MT-4 cell and found inactive, except 29, which showed inhibition of HIV-1 with EC50 value of 0.15 ± 0.1 μg/ml and a therapeutic index (SI) of 73. 相似文献
19.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):845-847
Abstract A series of cyclohexenyl nucleosides (1–8) were successfully prepared with moderate yield and their cytotoxicity and antiviral activity were investigated. Among the eight new compounds, only the diaminopurine analogue 8 showed pronounced activity against HSV-1, HSV-2. 相似文献
20.
《Nucleosides, nucleotides & nucleic acids》2013,32(12):2161-2170
Abstract 1-O-Acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-erythro-pentofuranose and 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose were coupled with 5-azacytosine to obtain α and β anomers of nucleosides. All four nucleosides were reduced to the corresponding dihydro derivatives and deblocked to give target compounds. All eight target compounds were evaluated in a series of human cancer cell lines in culture. Only 2′-deoxy-4′-thio-5-azacytidine (3β) was found to be cytotoxic in all the cell lines and was further evaluated in vivo. Details of the synthesis and biological activity are reported. 相似文献