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Mitoxantrone

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Identification
Molecular formula
C22H28N4O6
CAS number
65271-80-9
IUPAC name
methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylate
State
State

Mitoxantrone is a solid at room temperature. While typically encountered in its solid form, it is often formulated into a liquid solution for its primary use in clinical applications.

Melting point (Celsius)
256.00
Melting point (Kelvin)
529.00
Boiling point (Celsius)
500.00
Boiling point (Kelvin)
773.00
General information
Molecular weight
444.50g/mol
Molar mass
444.4960g/mol
Density
1.4200g/cm3
Appearence
Mitoxantrone appears as a dark blue crystalline solid. It is known for its intense blue color, which is used in its application as an antineoplastic agent.
Comment on solubility

Solubility of Methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylate

The solubility of methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylate can be influenced by various factors owing to its complex structure. Here are the key points to consider:

  • Polarity: The presence of multiple functional groups such as amino, methoxy, and carboxylate can enhance solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds, especially with the hydroxyl group, increases interactions with solvents.
  • Solvent Choice: Solubility may vary significantly between organic solvents and aqueous environments. It’s often more soluble in organic solvents like ethanol and methanol.
  • pH Effects: The solubility may be pH-dependent, particularly due to the carboxylic acid group, which can ionize and improve solubility in alkaline conditions.

In conclusion, while structural complexity often implies varied solubility patterns, this compound’s multifunctional nature may allow for favorable solubility characteristics in appropriate solvents. It's essential to conduct specific solubility tests for precise applications.

Interesting facts

Methyl 5-Amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylate

This compound is a fascinating example of the intersection of organic chemistry and pharmacology. Often referred to in the field as an *optimistic candidate for drug development*, its multiple functional groups present unique opportunities for therapeutic application. Here are some intriguing facts:

  • Diverse Functional Groups: The compound boasts an intricate structure with various functional groups including amino, methoxy, and hydroxyl, which can significantly influence biological activity.
  • Potential Anticancer Properties: Research has suggested that related compounds in the pyridine family often exhibit *antitumor activity*, positioning this compound as a possible lead candidate in cancer therapy studies.
  • Role as a Quinolone Derivative: As it features a quinolone moiety, this compound shares properties with many known antimicrobial agents, suggesting further avenues for investigation in infection control.
  • Complex Synthesis: The synthesis of this compound can be quite challenging, often requiring multi-step reactions. This complexity can be both a hurdle and a reward in exploring new pathways in organic synthesis.
  • Structure-Activity Relationship (SAR): The study of the structure-activity relationship allows chemists to modify the compound intentionally, enhancing its efficacy and reducing toxicity for therapeutic purposes.

In summary, this compound represents significant potential in medicinal chemistry, where its unique structural features may lead to advancements in drug design and development. As research continues, it will be exciting to see how this compound can be further optimized for clinical applications.

Synonyms
Methyl streptonigrin
3398-48-9
STREPTONIGRIN METHYL ESTER
NSC-45384
NSC45384
MLS000766273
SMR000528866
2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, methyl ester
H00548KV4H
methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylate
Picolinic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, methyl ester
Methyl ester streptonigrin
MES (VAN)
methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinate
NSC 45384
BRN 5324543
UNII-H00548KV4H
AI3-52460
STN-OCH3
methyl (4Z)-5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylate
CHEMBL2002947
SCHEMBL25015126
BDBM71262
cid_5359866
DTXSID70955558
CHEBI:232715
GLXC-04337
HMS2852I08
STREPTONIGRIN, METHYL ESTER
AKOS040747153
NCGC00246815-01
NCI60_004052
HY-123380
SR-01000775933
SR-01000775933-2
Q27279382
WLN: T66 BV EV GNJ CO1 DZ H- BT6NJ CZ DR BQ CO1 DO1& E1 FVO1
(4Z)-5-amino-6-(7-amino-5,8-diketo-6-methoxy-2-quinolyl)-4-(6-keto-4,5-dimethoxy-cyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid methyl ester
(4Z)-5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(4,5-dimethoxy-6-oxo-1-cyclohexa-2,4-dienylidene)-3-methyl-1H-pyridine-2-carboxylic acid methyl ester
2-Pyridinecarboxylic acid,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, methyl ester
methyl (4Z)-5-azanyl-6-[7-azanyl-6-methoxy-5,8-bis(oxidanylidene)quinolin-2-yl]-4-(4,5-dimethoxy-6-oxidanylidene-cyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylate
methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylate
Methyl 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylate
Picolinic acid,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, methyl ester
Picolinic acid,8-dihydro-7-methoxy-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, methyl ester
Picolinic acid,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, methyl ester