Cas no 129085-76-3 (1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)-)

The compound 1H-Imidazole-4-propanoic acid, α-[(1S)-1-amino-3-methylbutyl]-α-hydroxy-, (αR)-, is a chiral derivative of imidazole-propanoic acid featuring both amino and hydroxy functional groups. Its stereospecific structure, with defined (αR) and (1S) configurations, makes it valuable for applications in asymmetric synthesis and pharmaceutical research. The presence of the imidazole ring enhances its potential as a ligand or intermediate in metal coordination and bioactive molecule development. The branched alkyl chain contributes to its lipophilicity, broadening its utility in peptide modifications or prodrug design. This compound’s well-defined stereochemistry and multifunctional groups offer precise control in synthetic pathways, making it a versatile building block for specialized chemical and biochemical applications.
1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- structure
129085-76-3 structure
Product Name:1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)-
CAS No:129085-76-3
MF:C11H19N3O3
MW:241.286862611771
CID:166269
PubChem ID:131057
Update Time:2025-11-01

1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- Chemical and Physical Properties

Names and Identifiers

    • 1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)-
    • LEUHISTIN
    • Leuhistine
    • s*))--(r
    • Monoclonal Anti-SNCG antibody produced in mouse
    • alpha-(1-amino-3-methylbutyl)-alpha-hydroxy-1h-imidazole-4-propanoicaci(r
    • (2R,3S)-3-AMINO-2-HYDROXY-2-(1H-IMIDAZOL-4-YLMETHYL)-5-METHYLHEXANOIC ACID
    • (2R,3S)-3-Amino-2-hydroxy-5-methyl-2-[(1H-imidazol-4-yl)methyl]hexanoic acid
    • ((2R,3S)-3-AMINO-2-HYDROXY-2-(1H-IMIDAZOL-4-YLMETHYL)-5-METHYL)-5-METHYLHEXANOIC ACID
    • (2R,3S)-3-amino-2-hydroxy-2-(1H-imidazol-5-ylmethyl)-5-methylhexanoic acid
    • AKOS040747055
    • 1H-Imidazole-4-propanoic acid, alpha-(1-amino-3-methylbutyl)-alpha-hydroxy-, (R-(R*,S*))-
    • 129085-76-3
    • SCHEMBL12609365
    • (2R,3S)-2-((1H-imidazol-4-yl)methyl)-3-amino-2-hydroxy-5-methylhexanoic acid
    • 3-Amino-2-hydroxy-2-[(1H-imidazol-5-yl)methyl]-5-methylhexanoic acid
    • 3-amino-2-hydroxy-2-(1H-imidazol-4-ylmethyl)-5-methylhexanoic acid
    • DTXSID20926293
    • CHEBI:221454
    • Inchi: 1S/C11H19N3O3/c1-7(2)3-9(12)11(17,10(15)16)4-8-5-13-6-14-8/h5-7,9,17H,3-4,12H2,1-2H3,(H,13,14)(H,15,16)/t9-,11+/m0/s1
    • InChI Key: WZFDNGAENBEYMA-GXSJLCMTSA-N
    • SMILES: O[C@](C(=O)O)(CC1=CN=CN1)[C@H](CC(C)C)N

Computed Properties

  • Exact Mass: 241.14300
  • Monoisotopic Mass: 241.143
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 6
  • Complexity: 273
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: -2.3
  • Topological Polar Surface Area: 112

Experimental Properties

  • Color/Form: Not available
  • Density: 1.273
  • Boiling Point: 533.8 °C at 760 mmHg
  • Flash Point: 276.6 °C
  • Refractive Index: 1.575
  • PSA: 112.23000
  • LogP: 0.84160
  • Solubility: Not available

1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- Security Information

  • Storage Condition:-20°C

1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- Pricemore >>

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1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- Related Literature

Additional information on 1H-Imidazole-4-propanoicacid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)-

1H-Imidazole-4-propanoic Acid, a-[(1S)-1-Amino-3-Methylbutyl]-a-Hydroxy-, (aR)-: A Comprehensive Overview

The compound with CAS No. 129085-76-3, commonly referred to as 1H-imidazole-4-propanoic acid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)-, is a highly specialized organic molecule with significant potential in the fields of pharmacology and medicinal chemistry. This compound belongs to the class of imidazole derivatives, which are well-known for their diverse biological activities and applications in drug design. The imidazole ring serves as a critical structural motif, contributing to the molecule's stability and reactivity.

Recent advancements in chemical synthesis have enabled the precise construction of this compound, leveraging stereochemistry to achieve the desired R configuration at the alpha position. The (1S)-1-amino-3-methylbutyl group attached to the imidazole ring introduces unique steric and electronic properties, making this compound a promising candidate for various biological assays. Researchers have demonstrated that this compound exhibits potent antimicrobial activity, particularly against Gram-positive bacteria, which is attributed to its ability to disrupt bacterial cell membranes.

In addition to its antimicrobial properties, 1H-imidazole-4-propanoic acid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- has shown potential as a neuroprotective agent. Studies conducted in vitro have revealed its capacity to scavenge reactive oxygen species (ROS) and reduce oxidative stress in neuronal cells. This suggests that the compound could be developed into a therapeutic agent for neurodegenerative diseases such as Alzheimer's and Parkinson's disease.

The synthesis of this compound involves a multi-step process that incorporates advanced techniques such as asymmetric catalysis and stereochemical control. The use of chiral auxiliaries has been pivotal in achieving the desired stereochemistry at the alpha position. Furthermore, computational chemistry methods, including molecular docking and dynamics simulations, have been employed to predict the binding affinity of this compound to various biological targets. These studies have provided valuable insights into its mechanism of action and potential therapeutic applications.

Recent research has also explored the bioavailability of this compound, with findings indicating that it exhibits moderate absorption when administered orally. However, efforts are ongoing to optimize its pharmacokinetic properties through structural modifications and formulation strategies. These modifications aim to enhance solubility, stability, and bioavailability, thereby improving its suitability for clinical applications.

Another area of interest is the exploration of this compound's anti-inflammatory properties. Preclinical studies have demonstrated its ability to inhibit pro-inflammatory cytokines such as TNF-alpha and IL-6, suggesting its potential as an anti-inflammatory agent in chronic inflammatory diseases like arthritis and inflammatory bowel disease.

Moreover, the compound has shown promise in anticancer research, with studies indicating its ability to induce apoptosis in various cancer cell lines. The mechanism appears to involve modulation of key signaling pathways such as MAPK and NF-kB, which are critical for cancer cell survival and proliferation.

In conclusion, 1H-imidazole-4-propanoic acid, a-[(1S)-1-amino-3-methylbutyl]-a-hydroxy-, (aR)- represents a versatile molecule with multifaceted biological activities. Its potential applications span across antimicrobial therapy, neuroprotection, anti-inflammation, and anticancer treatment. Continued research into its synthesis, mechanism of action, and pharmacokinetics will undoubtedly pave the way for its translation into clinical practice.

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