dc.creator | Kollatos N., Mitsos C., Manta S., Tzioumaki N., Giannakas C., Alexouli T., Panagiotopoulou A., Schols D., Andrei G., Komiotis D. | en |
dc.date.accessioned | 2023-01-31T08:43:37Z | |
dc.date.available | 2023-01-31T08:43:37Z | |
dc.date.issued | 2020 | |
dc.identifier | 10.2174/1573406415666190225112950 | |
dc.identifier.issn | 15734064 | |
dc.identifier.uri | http://hdl.handle.net/11615/74978 | |
dc.description.abstract | Background: Nucleoside analogues are well-known antitumor, antiviral, and chemotherapeutic agents. Alterations on both their sugar and the heterocyclic parts may lead to significant changes in the spectrum of their biological activity and the degree of selective toxicity, as well as in their physicochemical properties. Method: C5-arylalkynyl-β-D-ribofuranonucleosides 3-6, 3΄-deoxy 12-15, 3΄-deoxy-3΄-C-methyl-β-D-ribofurananucleosides 18-21 and 2΄-deoxy-β-D-ribofuranonucleosides 23-26 of uracil, were synthesized using a one-step Sonogashira reaction under microwave irradiation and subsequent deprotection. Results: All newly synthesized nucleosides were tested for their antitumor or antiviral activity. Moderate cytostatic activity against cervix carcinoma (HeLa), murine leukemia (L1210) and human lymphocyte (CEM) tumor cell lines was displayed by the protected 3΄-deoxy derivatives 12b, 12c, 12d, and the 3΄-deoxy-3΄-methyl 18a, 18b, 18c. The antiviral evaluation revealed appreciable activity against Coxsackie virus B4, Respiratory syncytial virus, Yellow Fever Virus and Human Coronavirus (229E) for the 3΄-deoxy compounds 12b, 14, and the 3΄-deoxy-3΄-methyl 18a, 18c, 18d, accompanied by low cytotoxicity. Conclusion: This report describes the total and facile synthesis of modified furanononucleosides of uracil, with alterations on both the sugar and the heterocyclic portions. Compounds 12b, 14 and 18a,c,d showed noticeable antiviral activity against a series of RNA viruses and merit further biological and structural optimization investigations. © 2020 Bentham Science Publishers. | en |
dc.language.iso | en | en |
dc.source | Medicinal Chemistry | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85083054282&doi=10.2174%2f1573406415666190225112950&partnerID=40&md5=b36a2d9d68dab59dc8e5504c951ce69d | |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy 3' c methyl beta dextro ribofuranosyl) 5 iodouracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy 3' c methyl beta dextro ribofuranosyl) 5 [(2 fluorophenyl)ethynyl]uracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy beta dextro ribofuranosyl) 5 iodouracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy beta dextro ribofuranosyl) 5 [(2 chlorophenyl)ethynyl]uracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy beta dextro ribofuranosyl) 5 [(2 fluorophenyl)ethynyl]uracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy beta dextro ribofuranosyl) 5 [(2,4,5 trimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy beta dextro ribofuranosyl) 5 [(2,5 dimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (2' o acetyl 5' o benzoyl 3' deoxy beta dextro ribofuranosyl) 5 [(6 methoxynaphthalene)ethynyl]uracil | en |
dc.subject | 1 (2',3',5' tri o acetyl beta dextro ribofuranosyl) 5 iodouracil | en |
dc.subject | 1 (2',3',5' tri o acetyl beta dextro ribofuranosyl) 5 [(2 chlorophenyl)ethynyl]uracil | en |
dc.subject | 1 (2',3',5' tri o acetyl beta dextro ribofuranosyl) 5 [(2 fluorophenyl)ethynyl]uracil | en |
dc.subject | 1 (2',3',5' tri o acetyl beta dextro ribofuranosyl) 5 [(2,4,5 trimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (2',3',5' tri o acetyl beta dextro ribofuranosyl) 5 [(2,5 dimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (2',3',5' tri o acetyl beta dextro ribofuranosyl) 5 [(6 methoxynaphthalene)ethynyl]uracil | en |
dc.subject | 1 (3' deoxy beta dextro ribofuranosyl) 5 [(2 chlorophenyl)ethynyl]uracil | en |
dc.subject | 1 (3' deoxy beta dextro ribofuranosyl) 5 [(2 fluorophenyl)ethynyl]uracil | en |
dc.subject | 1 (3' deoxy beta dextro ribofuranosyl) 5 [(2,4,5 trimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (3' deoxy beta dextro ribofuranosyl) 5 [(6 methoxynaphthalene)ethynyl]uracil | en |
dc.subject | 1 (beta dextro ribofuranosyl) 5 [(2 chlorophenyl)ethynyl]uracil | en |
dc.subject | 1 (beta dextro ribofuranosyl) 5 [(2 fluorophenyl)ethynyl]uracil | en |
dc.subject | 1 (beta dextro ribofuranosyl) 5 [(2,4,5 trimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (beta dextro ribofuranosyl) 5 [(2,5 dimethylphenyl)ethynyl]uracil | en |
dc.subject | 1 (beta dextro ribofuranosyl) 5 [(6 methoxynaphthalene)ethynyl]uracil | en |
dc.subject | 1,2 di o acetyl 5 o benzoyl 3 deoxy beta dextro ribofuranose | en |
dc.subject | 5 o benzoyl 3 deoxy 1,2 o isopropylidene a dextro ribofuranose | en |
dc.subject | antivirus agent | en |
dc.subject | cytotoxic agent | en |
dc.subject | nucleoside derivative | en |
dc.subject | pyrimidine derivative | en |
dc.subject | unclassified drug | en |
dc.subject | unindexed drug | en |
dc.subject | antineoplastic agent | en |
dc.subject | antivirus agent | en |
dc.subject | pyrimidine nucleoside | en |
dc.subject | antineoplastic activity | en |
dc.subject | antiviral activity | en |
dc.subject | Article | en |
dc.subject | controlled study | en |
dc.subject | Coronaviridae | en |
dc.subject | Coxsackievirus B4 | en |
dc.subject | cytostasis | en |
dc.subject | drug cytotoxicity | en |
dc.subject | drug design | en |
dc.subject | drug potency | en |
dc.subject | drug synthesis | en |
dc.subject | EC50 | en |
dc.subject | embryo | en |
dc.subject | female | en |
dc.subject | HeLa cell line | en |
dc.subject | human | en |
dc.subject | human cell | en |
dc.subject | Human coronavirus 229E | en |
dc.subject | Human respiratory syncytial virus | en |
dc.subject | IC50 | en |
dc.subject | L1210 cell line | en |
dc.subject | microwave irradiation | en |
dc.subject | nonhuman | en |
dc.subject | priority journal | en |
dc.subject | Sonogashira reaction | en |
dc.subject | Yellow fever virus | en |
dc.subject | animal | en |
dc.subject | cell proliferation | en |
dc.subject | chemistry | en |
dc.subject | drug effect | en |
dc.subject | mouse | en |
dc.subject | synthesis | en |
dc.subject | Animals | en |
dc.subject | Antineoplastic Agents | en |
dc.subject | Antiviral Agents | en |
dc.subject | Cell Proliferation | en |
dc.subject | Chemistry Techniques, Synthetic | en |
dc.subject | Drug Design | en |
dc.subject | HeLa Cells | en |
dc.subject | Humans | en |
dc.subject | Mice | en |
dc.subject | Pyrimidine Nucleosides | en |
dc.subject | Bentham Science Publishers | en |
dc.title | Design, synthesis, and biological evaluation of novel C5-modified pyrimidine ribofuranonucleosides as potential antitumor or/and antiviral agents | en |
dc.type | journalArticle | en |