127592-40-9

Basic information

• Product Name: 5-Chloro-2',3'-dideoxyuridine
• Synonyms: 5-Chloro-2',3'-dideoxyuridine
• CAS NO: 127592-40-9
• Molecular Formula: C₉H₁₁ClN₂O₄
• Molecular Weight: 246.65
• Mol File: 127592-40-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.55g/cm³
• Refractive Index: 1.613
• CAS DataBase Reference: 5-Chloro-2',3'-dideoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2',3'-dideoxyuridine(127592-40-9)
• EPA Substance Registry System: 5-Chloro-2',3'-dideoxyuridine(127592-40-9)

Safety Data

• Hazardous Substances Data: 127592-40-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11ClN2O4/c10-6-3-12(9(15)11-8(6)14)7-2-1-5(4-13)16-7/h3,5,7,13H,1-2,4H2,(H,11,14,15)/t5-,7+/m0/s1

Upstream product

• 81252-66-6 Benzoic acid 5-(5-chloro-4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 81252-66-6 Benzoic acid (2S,5R)-5-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 62396-80-9 (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 56-86-0 L-glutamic acid 
• 187458-07-7 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate 
• 28616-91-3 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil 
• 951317-13-8 5'-O-acetyl-5-chloro-2',3'-dideoxyuridine 

Relevant articles and documents

NMR studies of pyrimidinic nucleosides derived from 2,3-dideoxy-d-ribose with inhibitory activity on LINE-1 mobility

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Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides

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

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.