myo-Inositol 1-(5-bromo-4-chloro-1H-indol-3-yl hydrogen phosphate) monoammonium salt
[CAS# 212515-11-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: myo-Inositol 1-(5-bromo-4-chloro-1H-indol-3-yl hydrogen phosphate) monoammonium salt
• Synonyms: B 7404
• Molecular Formula: C₁₄H₁₆BrClNO₉P^.NH₃
• Molecular Weight: 505.64
• CAS Registry Number: 212515-11-2
• SMILES: C1=CC(=C(C2=C1NC=C2OP(=O)([O-])OC3[C@@H]([C@H](C([C@H]([C@H]3O)O)O)O)O)Cl)Br.[NH4+]

Discovory and Applicatios

myo-Inositol 1-(5-bromo-4-chloro-1H-indol-3-yl hydrogen phosphate) monoammonium salt is a chemically modified derivative of myo-inositol, a cyclohexanehexol compound widely recognized for its role in cellular signaling and membrane biochemistry. In this compound, a 5-bromo-4-chloro-1H-indol-3-yl group is covalently linked to the first carbon of myo-inositol through a hydrogen phosphate ester bond, and the compound exists as its monoammonium salt form. This structural modification introduces halogenated indole functionality onto the inositol backbone, which influences both the chemical properties and potential biological activities of the molecule.

The compound is synthesized by the selective phosphorylation of myo-inositol at the 1-position with the phosphate group bearing the 5-bromo-4-chloro-1H-indol-3-yl substituent. The bromine and chlorine atoms on the indole ring contribute to the molecule's chemical stability and may modulate interactions with biological targets, given the importance of halogen atoms in enhancing binding affinity and specificity in drug design. The ammonium salt form enhances solubility and stability, facilitating handling and application in aqueous environments.

In research contexts, myo-inositol derivatives phosphorylated at specific positions serve as crucial tools in the study of phosphoinositide signaling pathways, which regulate diverse cellular processes including proliferation, differentiation, and apoptosis. The addition of a halogenated indole moiety may enable the compound to act as a probe or inhibitor with unique binding properties to enzymes or receptors involved in inositol phosphate metabolism.

Applications of this compound are primarily focused on biochemical and pharmacological research. It can be utilized to investigate enzyme mechanisms such as those of kinases and phosphatases that act on inositol phosphates, or to explore receptor-ligand interactions where indole derivatives are relevant. The unique structural features of the molecule may also permit exploration of membrane interactions or modulation of signaling cascades, expanding the understanding of halogenated indole effects in a biological setting.

Overall, myo-Inositol 1-(5-bromo-4-chloro-1H-indol-3-yl hydrogen phosphate) monoammonium salt represents a specialized chemical tool combining the signaling relevance of myo-inositol phosphate esters with the chemical versatility and biological significance of halogenated indole groups. Its synthesis and use provide insights into cellular signaling pathways and offer potential for developing novel biochemical probes or therapeutic leads.