127592-40-9Relevant articles and documents
NMR studies of pyrimidinic nucleosides derived from 2,3-dideoxy-d-ribose with inhibitory activity on LINE-1 mobility
Banuelos-Sanchez, Guillermo,Franco-Montalban, Francisco,Tamayo, Juan A.
, p. 118 - 125 (2019/11/28)
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Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides
Rai, Dinesh,Johar, Monika,Srivastav, Naveen C.,Manning, Tracey,Agrawal,Kunimoto, Dennis Y.,Kumar, Rakesh
, p. 4766 - 4774 (2008/03/12)
The prevalence of tuberculosis (TB) and mutidrug-resistant tuberculosis (MDR-TB) has been increasing, leading to serious infections, high mortality, and a global health threat. Here, we report the identification of a novel class of dideoxy nucleosides as potent and selective inhibitors of Mycobacterium bovis, Mycobacterium tuberculosis, and drug-resistant Mycobacterium tuberculosis. A series of 5-acetylenic derivatives of 2′,3′-dideoxyuridine (3-8) and 3′-fluoro-2′,3′-dideoxyuridine (22-27) were synthesized and tested for their antimycobacterial activity against M. bovis, M. tuberculosis, and M. avium. 2′,3′-Dideoxyuridine possessing 5-decynyl, 5-dodecynyl, 5-tridecynyl, and 5-tetradecynyl substituents (4-7) exhibited the highest antimycobacterial activity against all three mycobacteria. In contrast, in the 3′-fluoro-2′,3′-dideoxyuridine series, a 5-tetradecynyl analogue (26) displayed the most potent activity against these mycobacteria. Among other derivatives, 5-bromo-2′,3′-dideoxycytidine (11), 5-methyl-2′,3′-dideoxycytidine (12), and 5-chloro-4-thio-2′, 3′-dideoxyuridine (19) exhibited modest inhibition of M. bovis and M. tuberculosis. In the series of dideoxy derivatives of adenosine, guanosine, and purines, 2-amino-6-mercaptoethyl-9-(2,3-dideoxy-β-D-glyceropentofuranosyl) purine (32) and 2-amino-4-fluoro-7-(2,3-dideoxy-β-D-glyceropentofuranosyl) pyrrolo[2,3-d]-pyrimidine (35) were the most efficacious against M. bovis and M. tuberculosis, and M. avium, respectively.
Analogs of pyrimidine nucleosides. 16. Racemic 2′,3′-dideoxynucleosides and their derivatives
Kaulinya,Liepin'sh,Lidak,Zhuk
, p. 85 - 93 (2007/10/02)
The chlorination of 2-halomethyltetrahydrofurans and acyl derivatives of tetrahydrofuryl alcohol wasstudied; mixtures of 2,5- and 2,2-disubstituted tetrahydrofurans are formed as a result of the reaction. 2,4-Bis(trimethylsilyl) derivatives of uracil, 5-substituted uracils, and cytosine are alkylated by the resulting mixtures of α-chloro ethers without separation, and mixtures of cis and transisomers of 1-(5-substituted-2-tetrahydrofuryl) and 1-(2-substituted-2-tetrahydrofuryl) derivatives of uracil, 5-substituted uracils, and cytosine are obtained. The reaction products were identified onthe basis of their PMR spectra.