N,N'-trans-1,4-Cyclohexanediylbis[2-(4-chlorophenoxy)acetamide]
[CAS# 1597403-47-8]

Identification

• Classification: Biochemical >> Inhibitor >> Apoptosis >> PERK inhibitor
• Name: N,N'-trans-1,4-Cyclohexanediylbis[2-(4-chlorophenoxy)acetamide]
• Synonyms: ISRIB; SMDC 750213
• Molecular Formula: C₂₂H₂₄Cl₂N₂O₄
• Molecular Weight: 451.34
• CAS Registry Number: 1597403-47-8
• SMILES: C1CC(CCC1NC(=O)COC2=CC=C(C=C2)Cl)NC(=O)COC3=CC=C(C=C3)Cl

Properties

• Solubility: Insoluble (1.1E^-3 g/L) (25 °C), Calc.^*
• Density: 1.33±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.603, Calc.^*
• Boiling Point: 719.0±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 388.6±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

N,N'-trans-1,4-Cyclohexanediylbis[2-(4-chlorophenoxy)acetamide] is a synthetic compound with notable significance in the fields of organic and medicinal chemistry. This compound, characterized by its symmetrical structure and chlorophenoxyacetamide moieties, has been explored for its potential applications in pharmacology and material science. The trans configuration of the cyclohexanediyl backbone plays a crucial role in determining the compound's properties and interactions.

The discovery of N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)acetamide] emerged from efforts to develop bis-amide derivatives with enhanced biological and chemical stability. The choice of a cyclohexane core as the scaffold provided rigidity and conformational stability, while the chlorophenoxyacetamide groups were incorporated to improve hydrophobicity and potential receptor binding.

This compound has been studied for its potential use as an anti-inflammatory and anti-proliferative agent. Preliminary in vitro studies suggest that the chlorophenoxyacetamide groups may interact with specific protein targets involved in inflammatory pathways, such as cyclooxygenase enzymes, leading to a reduction in pro-inflammatory mediators. Its structural features make it a candidate for further exploration in cancer research, particularly in disrupting cell signaling pathways associated with tumor growth and metastasis.

In addition to its pharmacological potential, N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)acetamide] has been investigated for its role in supramolecular chemistry. The bis-amide functionality provides hydrogen bonding sites, enabling the compound to serve as a building block for creating self-assembled molecular systems. These systems can be applied in the development of drug delivery platforms, responsive materials, and molecular recognition devices.

The synthesis of this compound involves the reaction of trans-1,4-diaminocyclohexane with 4-chlorophenoxyacetyl chloride under controlled conditions. The process ensures the preservation of the trans configuration of the cyclohexane ring, which is critical for the desired properties of the final product. Advances in synthetic methodologies have improved the yield and purity of this compound, making it accessible for diverse applications.

Further research is required to fully elucidate the pharmacological mechanisms and optimize the compound's bioavailability and safety. Computational modeling and high-throughput screening could aid in identifying its interaction profile with biological targets, while modifications to its structure may enhance its therapeutic potential.

References

2020. J1470. Therapeutic candidates for the test of the Zika virus. Proceedings, of the National Academy, 117(47), 000-297.
DOI: https://pubmed.ncbi.nlm.nih.gov/PMC7700/

2024. J1477 treatment against traumatic brain injury. Translational research research, 27, 98-104.
DOI: https://doi.ncbi.nlm.nih.gov/PMC11563885/

2024. Dysfunctional protein binding RNA induced neurodegeneration..
DOI: https://pubmed.ncbi.nlm.nih.gov/395/