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Camptothecin

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Identification
Molecular formula
C20H16N2O4
CAS number
7689-03-4
IUPAC name
5-bromo-N-(2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
State
State

Camptothecin is a solid compound at room temperature. It is generally found in its crystalline form and is not soluble in water, but is soluble in some organic solvents such as dimethyl sulfoxide (DMSO), acetone, and methanol.

Melting point (Celsius)
267.00
Melting point (Kelvin)
540.20
Boiling point (Celsius)
655.30
Boiling point (Kelvin)
928.30
General information
Molecular weight
348.36g/mol
Molar mass
348.3550g/mol
Density
1.4690g/cm3
Appearence

Camptothecin appears as yellow crystalline needles or prisms. It can also be described as pale yellow in powder form. The compound is sensitive to light and air, requiring protection from both during storage to maintain its stability and coloration.

Comment on solubility

Solubility of 5-bromo-N-(2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (C20H16N2O4)

The solubility of this complex organic compound can be quite intricate, primarily due to its structural characteristics. Here's a closer look at factors influencing its solubility:

  • Polarity: The presence of multiple functional groups, such as hydroxyl (–OH) and carbonyl (C=O) moieties, may enhance its ability to interact with polar solvents, potentially increasing solubility in water and alcohols.
  • Hydrophobic components: Certain hydrophobic segments within the compound's structure can contribute to its overall solubility in organic solvents, such as dichloromethane or chloroform, while making it less soluble in polar environments.
  • Hydrogen bonding: The ability to form hydrogen bonds with solvent molecules can greatly affect solubility; compounds that can engage in hydrogen bonding often display enhanced solubility in polar solvents.

In conclusion, while this compound has notable polar features that may enhance solubility in aqueous solutions, its less polar, hydrophobic regions could limit this solubility. Understanding these traits allows for a better grasp of its behavior in various solvent environments, leading to implications for applications in fields like medicinal chemistry.

Interesting facts

Interesting Facts about 5-bromo-N-(2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

This complex compound, 5-bromo-N-(2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide, presents a fascinating example of organic chemistry’s ability to design intricate molecular architectures. Here are some noteworthy aspects:

  • Diverse Functional Groups: This compound contains a variety of functional groups, including hydroxyl, amide, and bromo, which contribute to its reactivity and potential biological activity.
  • Complex Structure: The presence of multiple cyclic components and stereogenic centers adds to the compound's complexity, making it a key interest in synthesis and structural biology.
  • Potential Biological Activity: Compounds like this are often investigated for their potential pharmaceutical applications, particularly in drug discovery efforts aimed at targeting various diseases.
  • Synthetic Challenges: The synthesis of such complicated molecules requires a deep understanding of organic synthesis techniques and mechanisms, showcasing the creativity and skill of chemists.
  • Applications in Material Science: Beyond its biological implications, the unique structural features of this compound could render it useful in the development of new materials with specific properties.

As a chemistry student or researcher, exploring this compound opens the door to discussing topics like structure-activity relationships (SAR) and the importance of molecular design in the field of medicinal chemistry. Furthermore, it encourages discussions about ongoing research and the methods utilized to synthesize and characterize such intricate molecules.

In the words of the renowned chemist Linus Pauling, "The best way to have a good idea is to have lots of ideas." This compound is certainly a reflection of the innovative thinking that drives the field of organic chemistry forward!

Synonyms
5-bromo-N-[2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
2 Bromo alpha ergocryptine
(8S)-2-Bromo alpha-ergocryptine
Bromokryptin
.alpha.-Bromoergocriptine
.alpha.-Bromoergocryptine
2-Bromo-.alpha.-ergokryptin
2-Bromo-.alpha.-ergokryptine
(8S)-2-Bromo-?-Ergocryptine
CHEMBL5306699
SCHEMBL11890530
CHEBI:91830
DTXSID90860276
OZVBMTJYIDMWIL-UHFFFAOYSA-N
LSM-1746
QCA70036
PDSP1_001105
PDSP2_001089
L000147
BRD-A69960130-066-01-4
Q27163626
2-Bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman
2-Bromo-12'-hydroxy-5'.alpha.-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman #
2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-5'.alpha.-ergotaman-3',6',18-trione
2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione, (5'.alpha.)
2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-.alpha.-(2-methylpropyl)ergotamin-3',6',18-trione