3-(2-Chloroacetyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide
[CAS# 72578-71-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 3-(2-Chloroacetyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide
• Synonyms: Ifosfamide acylate
• Molecular Formula: C₇H₁₃N₂PO₃Cl₂
• Molecular Weight: 275.07
• CAS Registry Number: 72578-71-3
• SMILES: C1CN(P(=O)(OC1)NCCCl)C(=O)CCl

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 355.0±52.0 °C 760 mmHg (Calc.)^*
• Flash point: 168.5±30.7 °C (Calc.)^*
• Index of refraction: 1.516 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06 Danger
• Risk Statements: H301-H311-H314-H331
• Safety Statements: P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P403+P233-P405-P501

Discovery and Applications

3-(2-Chloroacetyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide is a chemical compound belonging to the class of oxazaphosphorines, which are characterized by a five-membered ring structure containing both oxygen and phosphorus atoms. This compound features a combination of functional groups, including a chloroacetyl group and a chloroethylamino group, which contribute to its potential biological activity.

The discovery and development of oxazaphosphorines, such as this compound, are significant in the field of medicinal chemistry, particularly for their potential application in cancer therapy. Oxazaphosphorines are known for their ability to release active alkylating agents under certain conditions, which can interfere with DNA replication and transcription, leading to cell death. This class of compounds has been explored for its cytotoxic properties, making them of interest for the treatment of various cancers.

The structure of 3-(2-chloroacetyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide includes several key functional groups that contribute to its activity. The chloroacetyl group is a reactive electrophilic moiety that can form covalent bonds with nucleophilic sites on biomolecules, particularly within proteins and nucleic acids. Similarly, the chloroethylamino group is a potential alkylating agent that can interact with DNA, leading to DNA crosslinking or strand breaks. These interactions with genetic material are crucial to the compound's anticancer activity.

While specific clinical applications for this particular compound may not be fully established in the literature, its structural features suggest it could be investigated as a potential chemotherapeutic agent. The design of such compounds often aims to improve upon the efficacy and selectivity of existing treatments while minimizing side effects. The combination of phosphorine-based backbones with reactive functional groups has been explored to achieve these goals in various experimental treatments for cancer.

In the broader context of cancer chemotherapy, compounds like 3-(2-chloroacetyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide would likely be tested for their ability to inhibit tumor cell growth by disrupting cellular processes such as DNA replication and repair. The release of reactive species from such compounds can damage the genetic material within rapidly dividing cancer cells, which are more vulnerable to DNA damage due to their higher replication rates compared to normal cells.

Moreover, the presence of chlorine atoms in both the chloroacetyl and chloroethylamino groups can affect the compound's pharmacokinetic properties, including its solubility, stability, and the potential for selective targeting of cancer cells. The overall chemical design of this oxazaphosphorine derivative may allow it to be tested in combination with other chemotherapy agents, enhancing its overall effectiveness in cancer treatment regimens.

In summary, 3-(2-chloroacetyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide is an oxazaphosphorine-based compound with potential anticancer activity due to its alkylating properties. While further research is needed to fully explore its therapeutic potential, the structural characteristics of this compound suggest it could be an effective candidate for cancer treatment. The combination of chloroacetyl and chloroethylamino groups may enhance its ability to interact with cellular DNA and contribute to its cytotoxic effects on tumor cells.

References

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