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Azidothymidine (AZT)

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Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
1-[4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
State
State

At room temperature, azidothymidine is typically a solid powder. Due to its crystalline nature, it maintains structural integrity under standard conditions.

Melting point (Celsius)
123.00
Melting point (Kelvin)
396.15
Boiling point (Celsius)
413.30
Boiling point (Kelvin)
686.45
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
1.4281g/cm3
Appearence

Azidothymidine, commonly known as AZT, is usually found as a white to off-white crystalline powder. It is water-soluble, thus having clear to colorless or slightly yellow solutions depending on concentration.

Comment on solubility

Solubility of 1-[4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

The solubility of the compound 1-[4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione (C10H13N5O4) can be characterized by several intriguing factors:

  • Polarity: The presence of multiple functional groups such as azido, hydroxymethyl, and pyrimidine derivatives often contributes to enhanced polarity, potentially increasing solubility in polar solvents like water.
  • Hydrogen Bonding: The hydroxymethyl group can engage in hydrogen bonding, which may facilitate solvation and, therefore, improve solubility.
  • Solvent Compatibility: This compound is likely to be soluble in a range of solvents; however, it primarily suits solutions such as methanol and dimethyl sulfoxide (DMSO) owing to their polarity.
  • Temperature Dependency: Solubility may vary with temperature. Generally, increasing temperature enhances the solubility of solid solutes in liquids.

In conclusion, the solubility of 1-[4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione can be described as favorable in polar solvents. It is crucial to perform experimental assessments under controlled conditions to affirm and quantify these solubility characteristics.

Interesting facts

Interesting Facts about 1-[4-Azido-5-(Hydroxymethyl)Tetrahydrofuran-2-yl]-5-Methyl-Pyrimidine-2,4-Dione

This unique compound presents a fascinating intersection of organic and medicinal chemistry. Here are some noteworthy aspects that highlight its significance:

  • Functional Groups: The presence of both an azido group and a hydroxymethyl group indicates considerable potential for reactivity. Azides are often utilized in click chemistry, making this compound a strong candidate for synthetic modifications.
  • Tetrahydrofuran Ring: The tetrahydrofuran moiety contributes a cyclic structure that imparts unique steric and electronic properties, which can be crucial for interactions in biological systems.
  • Pyrimidine Core: The pyrimidine ring is integral in pharmaceuticals. Compounds containing pyrimidines are frequently explored for activities ranging from antiviral to anticancer effects.
  • Bioactivity Potential: Due to the combined presence of different functional groups, this compound might exhibit interesting bioactivities that could warrant further pharmacological investigation.
  • Medicinal Chemistry Applications: Researchers may apply such compounds as intermediates in the synthesis of more complex drugs, potentially leading to novel therapeutic agents.

As one delves deeper into the study of this compound, it's crucial to recognize that the intriguing combination of functional elements can lead to varied interactions with biological systems, making every research endeavor unique.
This could lead to not only greater understanding but also exciting new discoveries in the realm of medicinal chemistry!

Synonyms
NSC602670
3'-Azidothymidine
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
Azitidin
Timazid
Aztec
BW-A 509U
1-[(2R,4R,5S)-4-AZIDO-5-(HYDROXYMETHYL)OXOLAN-2-YL]-5-METHYL-PYRIMIDINE-2,4-DIONE
399024-19-2
Zidovudine, AZT
Thymidine, 8CI,
Trizivir (Salt/Mix)
3-Azido-3-deoxythymidine
CHEMBL178240
SCHEMBL13609910
component of Combivir (Salt/Mix)
HBOMLICNUCNMMY-UHFFFAOYSA-N
HMS3369K15
HMS3656A20
BCP03622
3'-Azido-3'-deoxythymidine, 98%
HB4602
STL451000
STL454167
ZINC04164448
AKOS015949577
AKOS037482514
CCG-229922
NCGC00015044-03
NCGC00015044-04
NCGC00015044-05
NCGC00094963-01
NCGC00094963-02
DA-49039
NCI60_004566
SY065461
EN300-295526
BRD-A33692381-001-01-9
1-(3-azido-2,3-dideoxypentofuranosyl)-2-hydroxy-5-methylpyrimidin-4(1H)-one
1-(3-azido-2,3-dideoxypentofuranosyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one
1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione