29706-85-2

Usage

Chemical Properties

Pale Yellow Solid

Upstream product

• 195885-79-1 1-[(2R,4S,5S)-4-Azido-5-(6-chloro-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 195885-78-0 1-[(2R,4S,5S)-4-Azido-5-(6-nitro-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 312750-67-7 O-(N^α-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate 
• 195885-82-6 1-[(2R,4S,5S)-4-Azido-5-(8-methoxy-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 195885-81-5 1-[(2R,4S,5S)-4-Azido-5-(6-methoxy-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 195885-85-9 1-[(2R,4S,5S)-4-Azido-5-(6,8-dimethyl-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 195885-83-7 1-[(2R,4S,5S)-4-Azido-5-(6-methyl-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 195885-84-8 cyclo-3-methylsaligenyl 3'-azido-2',3'-dideoxythymidine monophosphate 
• 195885-80-4 1-[(2R,4S,5S)-4-Azido-5-(2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 171284-24-5 4-butanoyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate 

Downstream Products

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 106060-89-3 3'-azido-3'-deoxythymidine-5'-diphosphate 
• 329237-23-2 O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 
• 244642-03-3 O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 
• 124930-59-2 3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester 

Relevant academic research and scientific papers

Design of new mononucleotide prodrugs: Aryl (SATE) phosphotriester derivatives

Synthesis, biological activities and decomposition kinetics of novel phosphotriester derivatives of 3′-azido-2′,3′-dideoxythymidine (AZT) bearing a S-tButyl-2-thioethyl (tBuSATE) group and L-tyrosinyl residues are reported. All the derivatives appeared to

Nucleotide Delivery from cycloSaligenyl-3′-azido-3′-deoxythymidine Monophosphates (cycloSal-AZTMP)

The application of our cycloSaligenyl- (cycloSal) pronucleotide concept to the approved anti-HIV dideoxynucleoside 3′-azido-3′-deoxythymidine AZT (1) is reported. This pronucleotide concept has been designed to deliver the corresponding 3′-azido-3′-deoxythymidine monophosphate AZTMP (2) by selective chemical hydrolysis from the lipophilic precursors cycloSal-AZTMP 4a-h. All derivatives 4a-h were synthesized using differently substituted salicyl alcohols 7a-h as starting materials. In hydrolysis studies, compounds 4 decomposed selectively releasing AZTMP (2) and the salicyl alcohols 7 following the designed tandem reaction. Furthermore, due to the electronic properties introduced by substituents, the half-lives of the triesters 4 could be ajusted over a wide range. Phosphotriesters 4 exhibited considerable biological activity in HIV-1 and HIV-2 infected wild-type human T-lymphocyte (CEM/O) cells, whereas, contrary to our expectations, nearly all activity was lost in HIV-2 infected thymidine-kinase-deficient CEM cells.

Synthesis, bioactivation and anti-HIV activity of 4-acyloxybenzyl bis(nucleosid-5'-yl) phosphates

4-Acyloxybenzyl bis(nucleosid-5'-yl) phosphates 7a-c and 9a-c were prepared as potential prodrugs of the anti-HIV nucleosides 3'-azido-3'- deoxythymidine (AZT) and 2',3'-dideoxyinosine (ddI) or their 5'- monophosphates. The anti-HIV activities of these triesters were determined in two T-cell lines. In a C8166 cell line they displayed activities comparable to and in some cases superior to AZT, but they also exhibited an increase in cytotoxicity. In a thymidine kinase deficient JM T-cell line the activity was reduced but was still superior to AZT. In the presence of porcine liver carboxyesterase (PLCE), triester 7b biodegrades to the diester 10 which, with phosphodiesterase, gives initially AZT monophosphate 3 and AZT.