Cas no 88547-15-3 (2,5-Piperazinedione,3-methyl-, (3R)-)

2,5-Piperazinedione,3-methyl-, (3R)- is a chiral piperazinedione derivative characterized by its methyl substitution at the 3-position and an (R)-configuration. This compound serves as a valuable intermediate in organic synthesis, particularly in the preparation of peptidomimetics and constrained peptide analogs. Its rigid, diketopiperazine scaffold enhances conformational stability, making it useful for studying structure-activity relationships in medicinal chemistry. The stereospecificity of the (3R)-configuration allows for precise control in asymmetric synthesis, while the methyl group introduces steric and electronic modifications to influence reactivity. This product is suitable for applications in pharmaceutical research, including the development of bioactive compounds and enzyme inhibitors.
2,5-Piperazinedione,3-methyl-, (3R)- structure
88547-15-3 structure
Product Name:2,5-Piperazinedione,3-methyl-, (3R)-
CAS No:88547-15-3
MF:C5H8N2O2
MW:128.129220962524
CID:709785
PubChem ID:12659067
Update Time:2025-06-12

2,5-Piperazinedione,3-methyl-, (3R)- Chemical and Physical Properties

Names and Identifiers

    • 2,5-Piperazinedione,3-methyl-, (3R)-
    • 2,5-Piperazinedione,3-methyl-,(3R)-(9CI)
    • 3-methyl-2,5-diketopiperazine
    • (R)-3-Methylpiperazine-2,5-dione
    • 88547-15-3
    • 2,5-Piperazinedione, 3-methyl-, (3R)-
    • CS-0046468
    • SCHEMBL13428066
    • A1-31071
    • (3R)-3-METHYLPIPERAZINE-2,5-DIONE
    • D72765
    • Inchi: 1S/C5H8N2O2/c1-3-5(9)6-2-4(8)7-3/h3H,2H2,1H3,(H,6,9)(H,7,8)/t3-/m1/s1
    • InChI Key: ICCHEGCKVBMSTF-GSVOUGTGSA-N
    • SMILES: O=C1[C@@H](C)NC(CN1)=O

Computed Properties

  • Exact Mass: 128.059
  • Monoisotopic Mass: 128.059
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 155
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 58.2A^2
  • XLogP3: -0.9

2,5-Piperazinedione,3-methyl-, (3R)- Pricemore >>

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Additional information on 2,5-Piperazinedione,3-methyl-, (3R)-

Introduction to 2,5-Piperazinedione,3-methyl-, (3R) and Its CAS No. 88547-15-3

The compound 2,5-Piperazinedione,3-methyl-, (3R), identified by the CAS number 88547-15-3, represents a significant advancement in the field of medicinal chemistry and pharmacology. This compound belongs to the piperazine derivatives family, a class of molecules known for their diverse biological activities and therapeutic potential. The specific stereochemistry denoted by the (3R) configuration underscores the importance of molecular chirality in determining pharmacological efficacy and safety.

In recent years, piperazine-based compounds have garnered considerable attention due to their role as key intermediates in the synthesis of various pharmaceuticals. The structural motif of piperazine, characterized by a six-membered ring containing two nitrogen atoms, provides a versatile scaffold for drug design. The presence of a methyl group at the 3-position and the dione functionality at the 2- and 5-positions in 2,5-Piperazinedione,3-methyl-, (3R) introduces unique electronic and steric properties that can modulate its interactions with biological targets.

One of the most compelling aspects of this compound is its potential application in the development of novel therapeutic agents. The (3R) configuration suggests that this molecule may exhibit specific binding affinities and metabolic profiles compared to its enantiomers. This stereochemical specificity is particularly crucial in drug development, where differences in enantiomeric purity can significantly impact a drug's efficacy and side effect profile.

Recent studies have highlighted the importance of piperazine derivatives in addressing various neurological and inflammatory disorders. The dione functional group in 2,5-Piperazinedione,3-methyl-, (3R) may contribute to its ability to interact with biological pathways involved in these conditions. For instance, piperazine derivatives have been investigated for their potential role in modulating neurotransmitter systems, making them promising candidates for treating conditions such as depression, anxiety, and chronic pain.

The synthesis of 2,5-Piperazinedione,3-methyl-, (3R) involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and enantiomeric purity. Advanced synthetic methodologies, including asymmetric catalysis and chiral resolution techniques, are often employed to achieve the desired stereochemical outcome. These synthetic strategies not only highlight the complexity of medicinal chemistry but also underscore the importance of innovative approaches in developing next-generation pharmaceuticals.

Beyond its potential therapeutic applications, 2,5-Piperazinedione,3-methyl-, (3R) has also attracted interest from researchers studying molecular recognition and supramolecular chemistry. The combination of nitrogen-rich heterocycles and functional groups like diones creates an ideal platform for designing molecules with specific binding properties. Such compounds can be used as probes or scaffolds for developing new diagnostic tools and materials with tailored functionalities.

The pharmacokinetic profile of 2,5-Piperazinedione,3-methyl-, (3R) is another critical aspect that warrants further investigation. Understanding how this compound is metabolized and eliminated by the body is essential for optimizing its therapeutic use. Preclinical studies using computational modeling and experimental techniques can provide valuable insights into its absorption, distribution, metabolism, excretion (ADME), and toxicological properties.

In conclusion,2,5-Piperazinedione,3-methyl-, (3R) represents a promising candidate for further exploration in medicinal chemistry. Its unique structural features and stereochemical configuration make it an intriguing molecule for developing novel therapeutic agents targeting neurological and inflammatory disorders. As research continues to uncover new applications for piperazine derivatives,88547-15-3 may play a pivotal role in advancing drug discovery efforts worldwide.

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