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Abacavir

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Identification
Molecular formula
C14H18N6O
CAS number
136470-78-5
IUPAC name
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
State
State

At room temperature, Abacavir is in solid form.

Melting point (Celsius)
165.00
Melting point (Kelvin)
438.15
Boiling point (Celsius)
438.10
Boiling point (Kelvin)
711.25
General information
Molecular weight
286.33g/mol
Molar mass
286.3320g/mol
Density
1.5200g/cm3
Appearence

Abacavir is typically seen as a white to off-white powder.

Comment on solubility

Solubility of 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile

The solubility of this complex organic compound can be influenced by several factors, reflecting its intricate structure. Here are some key points to consider:

  • Polarity: The presence of multiple hydroxyl (–OH) groups suggests that this compound is likely to be polar, enhancing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The ability to form hydrogen bonds due to the –OH groups may lead to a higher solubility in aqueous solutions.
  • Solvent Compatibility: This compound might have varying solubility in different solvents; for example, it may be soluble in alcohols and certain organic solvents, supporting diverse applications in different chemical environments.
  • Concentration Dependency: As with many compounds, solubility can increase at elevated temperatures, and may also be influenced by the concentration of the solute.

Overall, while specific solubility data for this compound may not be readily available, it is reasonable to infer that its structural features contribute to notable solubility in a variety of solvents due to the presence of hydroxyl groups and the potential for strong intermolecular interactions.

Interesting facts

Interesting Facts about 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile

This compound is a remarkable example of a complex organic molecule, characterized by its unique structural features and potential biological activity. Here are some intriguing insights:

  • Pharmacological Potential: Many derivatives of pyrrolo[2,3-d]pyrimidine are explored in drug discovery, showcasing anti-cancer and anti-viral properties that provide a promising avenue for pharmaceutical development.
  • Structure-Activity Relationship: The intricate arrangement of hydroxyl groups on the tetrahydrofuran ring plays a significant role in enhancing solubility and biological activity, making this molecule an interesting candidate for modification and study.
  • Chirality: The specific stereochemistry denoted by (2R,3R,4S,5R) is crucial for the molecule's interaction with biological targets, highlighting the importance of chirality in medicinal chemistry.
  • Synthetic Challenges: The synthesis of this compound can be quite challenging due to its complex ring structures and multiple chiral centers, often requiring advanced techniques in organic synthesis.
  • Research Interest: Structures similar to this compound are under intense study in the realm of nucleoside analogs which can mimic natural substrates for various biochemical reactions.

The engagement of this compound in ongoing research elucidates the vibrant intersection of chemistry and biology, encouraging chemists to devise innovative synthetic strategies while exploring its promising therapeutic applications.

Synonyms
TOYOCAMYCIN
Vengicide
Antibiotic 1037
Uramycin B
Siromycin
Cyanotubericidin
Ahygroscopin-B
7-Deaza-7-cyanoadenosine
Antibiotic E212
Unamycin B
Unamycin-B
Antibiotic A-399-Y4
Naritheracin
NSC 63701
NSC 99843
NSC-63701
E-212
A-399-Y4
Toyokamycin
Toyocamycin nucleoside
UNII-L7995C4D7F
BRN 0048454
4-Amino-5-cyano-7-(D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidine
L7995C4D7F
4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile
TOYOCAMYCIN [MI]
E-212-1
CHEBI:134606
4-26-00-01419 (Beilstein Handbook Reference)
7H-Pyrrolo(2,3-d)pyrimidine-5-carbonitrile, 4-amino-7-beta-D-ribofuranosyl-
NSC-99843
Antibiotic E 212
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Deazacyanoadenosine
B 181008
4-Amino-7-.beta.-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile
4-amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrrolo(2,3-d)pyrimidine-5-carbonitrile
7H-Pyrrolo(2,3-d)pyrimidine-5-carbonitrile, 4-amino-7-.beta.-D-ribofuranosyl-
xokjusayzuamgj-uhfffaoysa-n
606-58-6
4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
CHEMBL99668
toyocamycin monohydrate
4-amino-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
4-Amino-7-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
toyocamicin
Ara-toyocamycine
TO1
Antibiotic 1037?
Vengicide; Toyocamycin
3re4
Neuro 000027
SCHEMBL336095
cid_247955
XOKJUSAYZUAMGJ-WOUKDFQISA-N
DTXSID801031395
GLXC-07194
BDBM50049823
AKOS027380922
DB13916
NT44985
58151-27-2
DA-68279
HY-103248
CS-0026179
NS00011705
BRD-K26420709-001-01-7
Q27282806
Toyocamycin, >=98% (HPLC), from Streptomyces rimosus
4-Aminopyrrolo[2,3-d]pyrimidine-5-carbonitrile 7-(beta-D-ribofuranoside)
{7H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile,} 4-amino-7-.beta.-D-ribofuranosyl-
4-Amino-5-cyano-7-(?-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine;Vengicide;7-Deaza-7-cyanoadenosine;7-Cyano-7-deazaadenosine
4-amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
4-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
4-Amino-7-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile(toyocamycin)
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
4-amino-7-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile