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Ketoconazole

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Identification
Molecular formula
C26H28Cl2N4O4
CAS number
65277-42-1
IUPAC name
1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
State
State

Ketoconazole is typically a solid at room temperature.

Melting point (Celsius)
148.00
Melting point (Kelvin)
421.15
Boiling point (Celsius)
676.00
Boiling point (Kelvin)
949.15
General information
Molecular weight
531.43g/mol
Molar mass
531.4390g/mol
Density
1.3200g/cm3
Appearence

Ketoconazole appears as a white to off-white crystalline powder. It does not have a significant odor.

Comment on solubility

Solubility of 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone

The solubility of the compound with the chemical formula C26H28Cl2N4O4 is influenced by several factors, owing to its complex structure. This compound is a large organic molecule characterized by the presence of aromatic rings, halogen atoms, and dioxolane moieties, which can significantly affect its solubility properties. Below are key points regarding its solubility:

  • Polarity: The compound contains both polar and non-polar sections. The imidazole and dioxolane groups contribute to its polarity, while the chlorophenyl rings offer a more hydrophobic character.
  • Solvent Interaction: This compound is likely to be more soluble in organic solvents such as dimethyl sulfoxide (DMSO) or acetone, as these solvents can better interact with the hydrophobic parts of the molecule.
  • Temperature Dependence: Increased temperature may improve solubility due to enhanced molecular motion and reduced intermolecular interactions.
  • Potential Crystallinity: If the compound exhibits crystalline properties, its solubility could be lower in aqueous solutions, aligning with many larger organic and halogenated compounds.

In summary, while there is no direct articulation of solubility in water for this complex compound, it is reasonable to predict that it may exhibit moderate solubility in organic solvents due to its structural characteristics. Understanding these properties is critical for applications involving dissolution and reactivity.

Interesting facts

Interesting Facts about 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone

This compound is a noteworthy member of the class of piperazine derivatives, which have gained significant attention in medicinal chemistry. Here are some intriguing points regarding this unique compound:

  • Pharmacological Potential: Compounds like this one often exhibit biological activities that may be beneficial in treating various conditions, including but not limited to anxiety and depression. The structural diversity provided by the imidazole and dioxolane moieties might enhance its interaction with biological targets.
  • Complex Structure: Featuring an intricate arrangement of functional groups, this compound serves as a fascinating example of how slight modifications to a molecular structure can drastically change its properties and biological activities. The presence of the 2,4-dichlorophenyl ring highlights the importance of chlorinated compounds in pharmaceuticals, as halogenation can tune the lipophilicity and bioactivity.
  • Research Significance: This compound could be pivotal in ongoing research for developing new therapies. The blend of piperazine and imidazole rings could lead to innovative treatments, enhancing our understanding of drug design and efficacy.
  • Synthetic Routes: The synthesis of such compounds involves intricate organic reactions, showcasing the art of synthetic chemistry. Understanding the methods used to construct such diverse elements contributes to the skill set required in modern chemistry laboratories.
  • Analytical Techniques: The complexity of this compound necessitates the use of advanced analytical techniques for characterization, such as NMR, mass spectrometry, and X-ray crystallography, reinforcing the essential role of these methods in drug development.

In conclusion, 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone is not just a compound of interest due to its potential therapeutic applications; it is also an excellent demonstration of the complexities and intricacies involved in modern medicinal chemistry.

Synonyms
ketoconazole
79156-75-5
1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
65277-42-1
Xolegel
(Rac)-Ketoconazole
NSC317629
CHEBI:48339
R-41400
NSC 317629
1-[4-(4-{[2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
NSC-317629
1-(4-(4-((2-((1H-Imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethanone
1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethanone
fungarest;fungoral
SCHEMBL8408
Oprea1_683648
US8987315, Ketoconazole
CHEMBL157101
GTPL2568
SCHEMBL18258319
DTXSID20273956
BDBM151585
HMS3267K04
1-(4-(4-(((2S,4R)-2-((1H-Imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethanone
Piperazine, (+/-)-1-acetyl-4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, rel-
SYB70696
STL481884
AKOS015918262
DB01026
HY-W422288
KW 1414
NCI60_002728
DB-054790
DB-301239
CS-0569177
NS00077142
A19432
EN300-297716
Q407883
BRD-A76019558-001-01-0
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]-methoxy] phenyl]piperazine