84558-94-1

Basic information

• Product Name: 5-PROPYNYL-2'-DEOXYURIDINE
• Synonyms: 5-(1-PROPYNYL)-2'-DEOXYURIDINE;5-PROPYNYL-2'-DEOXYURIDINE;5-(1-Propynyl)-5-demethylthymidine;PYdU;2'-Deoxy-5-propynyluridine
• CAS NO: 84558-94-1
• Molecular Formula: C₁₂H₁₄N₂O₅
• Molecular Weight: 266.25
• Mol File: 84558-94-1.mol

Chemical Properties

• Appearance: /
• Density: 1.50±0.1 g/cm3(Predicted)
• PKA: 8.42±0.10(Predicted)
• CAS DataBase Reference: 5-PROPYNYL-2'-DEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PROPYNYL-2'-DEOXYURIDINE(84558-94-1)
• EPA Substance Registry System: 5-PROPYNYL-2'-DEOXYURIDINE(84558-94-1)

Safety Data

• Hazardous Substances Data: 84558-94-1(Hazardous Substances Data)

Usage

Uses

5-(1-Propynyl)-2’-deoxyuridine enhances DNA triplex formation and stability.

Upstream product

• 54-42-2 5-Iodo-2'-deoxyuridine 
• 74-99-7 prop-1-yne 
• 31356-86-2 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil 
• 4833-07-2 3',5'-di-O-benzoyl-5-iodo-2'-deoxyuridine 
• 74-88-4 methyl iodide 
• 84558-92-9 5-propynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine 

Downstream Products

• 383897-60-7 3-(β-D-2-deoxyribofuranosyl)-6-methylfuro[2,3-d]pyrimidin-2-one 
• 644962-92-5 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methyl-2-oxo-2,7-dihydro-pyrrolo[2,3-d]pyrimidin-3-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 644962-87-8 3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-2-one 
• 644962-78-7 3-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one 
• 382137-74-8 3-(β-D-2-deoxyribofuranosyl)-3,7-dihydro-6-methyl-2H-pyrrolo[2,3-d]pyrimidin-2-one 

Relevant articles and documents

2′-De-oxy-5-propynyluridine: A nucleoside with two conformations in the asymmetric unit

The title compound, 1-(2-de-oxy-Β-d-erythro-pentofuranos-yl)-5-(prop- 1-yn-yl)pyrimidin-2,4(1H,3H)-dione, C12H14N 2O5, shows two conformations in the crystalline state: conformer 1 adopts a C2′-endo (close to 2 E; S-type) sugar pucker and an anti nucleobase orientation [χ = -134.04 (19)°], while conformer 2 shows an S sugar pucker (twisted C2′-endo-C3′-exo), which is accompanied by a different anti base orientation [χ = -162.79 (17)°]. Both mol-ecules show a +sc (gauche, gauche) conformation at the exocyclic C4′ - C5′ bond and a coplanar orientation of the propynyl group with respect to the pyrimidine ring. The extended structure is a three-dimensional hydrogen-bond network involving intermolecular N - H...O and O - H...O hydrogen bonds. Only O atoms function as H-atom acceptor sites.

Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria

We herein report a new category of 5-substituted pyrimidine nucleosides as potent inhibitors of mycobacteria. A series of 5-alkynyl derivatives of 2′-deoxyuridine (1-8), 2′-deoxycytidine (9-14), uridine (15-17), and 2′-O-methyluridine (18, 19) were synthe

Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: A general protocol potentially useful for the synthesis of short-lived 11CH3-labeled PET tracers with a 1-propynyl group

The Pd(0)-mediated rapid coupling (trapping) reaction of methyl iodide with an excess amount of alkynyltributyl-stannane has been developed with the aim to incorporate a short-lived 11C-labeled methyl group into biologically active organic compounds with a 1-propynyl structural unit.

Pyrrolo-dC and pyrrolo-C: Fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides

Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-β-D-ribofuranosyl)-3H-pyrrolo[2,3- d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where

Synthesis and some biochemical properties of a novel 5,6,7,8-tetrahydropyrimido[4,5-c]pyridazine nucleoside

A novel nucleoside analogue is described based on the pyridazine ring system. The nucleoside was successfully incorporated into DNA via both its phosphoramidite and 5′-triphosphate derivatives. Enzymatically, the analogue behaves essentially as thymidine:

Synthesis and enzymatic incorporation of a novel, bicyclic pyrimidine nucleoside: A thymidine mimic

Nucleophilic ring-opening and rearrangement reaction of a furanopyrimidine nucleoside with anhydrous hydrazine provided a novel, 6,6-bicyclic pyrimidopyridazin-7-one nucleoside (dH, 4), whose structure was confirmed by X-ray crystallography. This novel nucleoside was converted to its 5′-triphosphate (dHTP) for studies with DNA polymerases and incorporated into a template by using standard phosphoramidite chemistry. In the template, dH directed the incorporation of dATP and to a lesser extent dGTP into the transcript and dHTP was efficiently incorporated at the 3′-end of a primer opposite dA using both exonuclease free Klenow fragment (KF exo-) and Taq DNA polymerases and extended with natural dNTPs.

Inhibition of tumor necrosis factor alpha (TNFα) expression and function in vitro by modified antisense oligonucleotides

Antisense oligonucleotides containing C-5 hexynyl/propynyl modified pyrimidines were synthesized using solid phase phosphoramidite chemistry. These modified oligonucleotides were found to have significant inhibitory activity against TNFα production in vit

Oligodeoxynucleotides Containing C-5 Propyne Analogs of 2'-Deoxyuridine and 2'-Deoxycytidine

Oligodeoxynucleotides (ODN) containing 5-(1-propynyl)-2'-deoxyuridine and 5-(1-propynyl)-2'-deoxycytidine significantly enhance double-helix formation with single strand RNA and 5-(1-propynyl)-2'-deoxyuridine significantly enhances triple-helix formation with double stranded DNA.

Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

A number of structurally related 5-substituted pyrimidine 2'-deoxyrubinucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.