Cytoxal alcohol
[CAS# 14504-75-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: Cytoxal alcohol
• Synonyms: bis(2-chloroethyl)amino-(3-hydroxypropylamino)phosphinic acid
• Molecular Formula: C₇H₁₇Cl₂N₂O₃P
• Molecular Weight: 279.10
• CAS Registry Number: 14504-75-7
• SMILES: C(CNP(=O)(N(CCCl)CCCl)O)CO

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.52, Calc.^*
• Boiling Point: 436.5±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 217.8±31.5 ºC, Calc.^*

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

Discovory and Applicatios

Cytoxal alcohol is a phosphorodiamidate compound with the molecular formula C₇H₁₇Cl₂N₂O₃P. It is also known by its systematic name, N,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)phosphorodiamidic acid. This compound is characterized by the presence of two 2-chloroethyl groups and a 3-hydroxypropyl group attached to a phosphorodiamidic acid core. Cytoxal alcohol is often encountered as a salt formed with cyclohexylamine, resulting in a compound with the molecular formula C₁₃H₃₀Cl₂N₃O₃P.

The compound was developed during research into alkylating agents, particularly those targeting DNA for potential therapeutic applications. Its structure, featuring bis(2-chloroethyl) groups, is reminiscent of other alkylating agents known for their ability to form cross-links in DNA strands, thereby inhibiting DNA replication and transcription. The inclusion of a hydroxypropyl group and the phosphorodiamidate moiety was intended to modulate the compound's reactivity and solubility, potentially enhancing its pharmacological properties.

Cytoxal alcohol has been studied for its potential cytotoxic effects, particularly in the context of cancer research. Its mechanism of action is believed to involve the alkylation of nucleophilic sites in DNA, leading to the formation of cross-links that disrupt DNA function. This mode of action is similar to that of other nitrogen mustard derivatives, which have been used as chemotherapeutic agents. The compound's ability to interfere with DNA processes makes it a candidate for further investigation in the development of anticancer therapies.

In addition to its potential therapeutic applications, Cytoxal alcohol has been utilized in genetic toxicity studies. Specifically, it has been evaluated using the Ames test, a widely used assay that assesses the mutagenic potential of chemical compounds. In this test, the compound is exposed to strains of Salmonella typhimurium and Escherichia coli to determine its ability to induce mutations. The results of such studies contribute to the understanding of the compound's genotoxic profile and inform risk assessments related to its use.

From a chemical standpoint, Cytoxal alcohol exhibits properties typical of organophosphorus compounds. It has a relatively high boiling point and low vapor pressure, indicating low volatility under standard conditions. The compound is soluble in water, which facilitates its use in aqueous biological assays. Its stability and reactivity are influenced by the presence of the chloroethyl groups, which are susceptible to nucleophilic substitution reactions, a feature that underlies its alkylating activity.

Safety considerations are paramount when handling Cytoxal alcohol, given its potential cytotoxic and genotoxic effects. Appropriate protective measures, including the use of personal protective equipment and containment strategies, are necessary to minimize exposure. Disposal of the compound must adhere to regulations governing hazardous chemical waste to prevent environmental contamination.

In summary, Cytoxal alcohol is a phosphorodiamidate compound with structural features that confer alkylating activity, making it of interest in the field of cancer research. Its development was part of efforts to create compounds capable of interfering with DNA function, and it has been studied for both its therapeutic potential and genetic toxicity. The compound's chemical properties and safety profile necessitate careful handling in research settings.

References

1992. National Toxicology Program Chemical Repository Database. National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health