108895-47-2Relevant articles and documents
Antimycobacterial activities of 5-alkyl (or halo)-3′-substituted pyrimidine nucleoside analogs
Srivastav, Naveen C.,Shakya, Neeraj,Bhavanam, Sudha,Agrawal, Amogh,Tse, Chris,Desroches, Nancy,Kunimoto, Dennis Y.,Kumar, Rakesh
supporting information; scheme or table, p. 1091 - 1094 (2012/03/26)
Several 5-alkyl (or halo)-3′-azido (amino or halo) analogs of pyrimidine nucleosides have been synthesized and evaluated against Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium. Among these compounds, 3′-azido-5-ethyl-2′,3′-dideoxyuridine (3) was found to have significant antimycobacterial activities against M. bovis (MIC 50 = 1 μg/mL), M. tuberculosis (MIC50 = 10 μg/mL) and M. avium (MIC50 = 10 μg/mL).
Antiviral activity of various 1-(2′-Deoxy-β- d -lyxofuranosyl), 1-(2′-Fluoro-β- d -xylofuranosyl), 1-(3′-Fluoro-β- d -arabinofuranosyl), and 2′-fluoro-2′,3′-didehydro-2′, 3′-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and human hepatitis B virus (HBV) replication
Srivastav, Naveen C.,Shakya, Neeraj,Mak, Michelle,Agrawal, Babita,Tyrrell, D. Lorne,Kumar, Rakesh
experimental part, p. 7156 - 7166 (2010/12/19)
Despite the existence of successful vaccine and antiviral therapies, infection with hepatitis B virus (HBV) continues to be a major global cause of acute and chronic liver disease and high mortality. We synthesized and evaluated several lyxofuranosyl, 2′-fluoroxylofuranosyl, 3′- fluoroarabinofuranosyl, and 2′-fluoro-2′,3′-didehydro- 2′,3′-dideoxyribose pyrimidine nucleoside analogues for antiviral activities against hepatitis B virus. Among the compounds examined, 1-(2-deoxy-β-d-lyxofuranosyl)thymine (23), 1-(2-deoxy-β-d- lyxofuranosyl)-5-trifluoromethyluracil (25), 1-(2-deoxy-2-fluoro-β-d- xylofuranosyl)uracil (38), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)thymine (39), 2′,3′-dideoxy-2′,3′-didehydro-2′- fluorothymidine (48), and 2′,3′-dideoxy-2′,3′-didehydro- 2′-fluoro-5-ethyluridine (49) were found to possess significant anti-HBV activity against DHBV in primary duck hepatocytes with EC50 values of 4.1, 3.3, 40.6, 3.8, 0.2, and 39.0 μM, respectively. Compounds 23, 25, 39, 48, and 49 (EC50 = 41.3, 33.7, 19.2, 2.0-4.1, and 39.0 μM, respectively) exhibited significant activity against wild-type human HBV in 2.2.15 cells. Intriguingly, 25, 39, 48, and 49 retained sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and 48 emerged as an effective inhibitor of drug-resistant HBV with an EC50 of 4.1 μM. In contrast, 50% inhibition could not be achieved by lamivudine at 44 μM concentration in the drug-resistant strain. The compounds investigated did not show cytotoxicity to host cells up to the highest concentrations tested.
Structure-Activity Relationships of Pyrimidine Nucleosides as Antiviral Agents for Human Immunodeficiency Virus Type 1 in Peripheral Blood Mononuclear Cells
Chu, Chung K.,Schinazi, Raymond F.,Ahn, Moon K.,Ullas, Giliyar V.,Gu, Zi P.
, p. 612 - 617 (2007/10/02)
The structure-activity relationships of several pyrimidine nucleosides related to 3'-azido-3'-deoxythymidine (AZT) were determined in human immunodeficiency virus type 1 (HIV-1) infected human peripheral blood mononuclear cells.These studies indicated tha
Pyrimidine derivatives
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, (2008/06/13)
Compounds of the formula STR1 wherein R1 is halogen, C1-4 -alkyl, halo-(C1-4 -alkyl) or C2-4 -alkanoyl, R2 is hydrogen, hydroxy, C1-4 alkoxy, C1-4 -alkylthio or phenyl-(C1-4 -alkoxy) or , when X is O, also acyloxy, R3 is hydrogen or C1-4 -alkyl, R4 is a carbocyclic group or a heterocyclic group, R5 is hydrogen or fluorine, m stands for zero, 1 or 2, X is O or NH and Y is a direct bond, --CH=CH--, --C C-- or a group of the formula of in which A is a C1-8 alkylene group which is optionally substituted by one or two phenyl groups, Z is O, S, SO or SO2 and n stands for zero or 1, with the proviso that R1 is different from iodine, when R2 is hydroxy or benzoyloxy, R3 is hydrogen, R4 is unsubstituted phenyl, R5 is hydrogen, m stands for zero, X is O, and Y is a direct bond, and tautomers thereof, which possess antiviral activity and can therefore be used in the form of medicaments for the control and prevention of viral infections are described. The compounds of formula I can be prepared according to known methods.
3'-Substituted 2',3'-Dideoxynucleoside Analogues as Potential Anti-HIV (HTLV-III/LAV) Agents
Herdewijn, Piet,Balzarini, Jan,Clerq, Erik De,Pauwels, Rudi,Baba, Masanori,et al.
, p. 1270 - 1278 (2007/10/02)
A series of 2',3'-unsaturated and 3'-substituted 2',3'-dideoxynucleoside analogues of purines and pyrimidines have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV).The 2',3'-unsaturated analogues of 2',3'-dideoxycytidine (ddeCyd) and 2',3'-dideoxythymidine (ddeThd), 3'-azido-2',3'-dideoxythymidine (AzddThd), 3'-fluoro-2',3'-dideoxythymidine, 2',3'-dideoxycytidine (ddCyd), and 2',3'-dideoxyadenosine (ddAdo) emerged as the most potent inhibitors of HIV-induced cytopathogenicity in the human T lymphocyte cell lines ATH8 and MT4.In ATH8 cells ddCyd, ddeCyd, and ddAdo had the highest therapeutic index whereas in MT4 cells AzddThd, ddThd, ddCyd, and ddAdo were the most selective.Derivatives from ddThd in which the substituent group was linked to the 3'-carbon atom via a thio, sulfonyl, or oxygen bridge were far less inhibitory to HIV than was AzddThd.
2',3'-dideoxy-5-substituted uridines and related compounds as antiviral agents
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, (2008/06/13)
A compound which exhibits antiviral activity towards HTLV-III/LAV, having the formula: STR1 wherein R4 is O or NH; R5 is a C2-4 alkyl group or a C3-4 cycloalkyl group, wherein said alkyl group or cycloalkyl grou
