Cas no 145438-95-5 ((2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid)

(2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid is a chiral bicyclic amino acid derivative featuring a rigid octahydroindole scaffold. Its stereochemically defined structure, with (2R,3aR,7aS) configuration, makes it a valuable intermediate in asymmetric synthesis and pharmaceutical applications. The compound’s constrained conformation enhances selectivity in peptidomimetic design and ligand-receptor interactions. Its carboxylic acid functionality allows for further derivatization, enabling incorporation into complex molecular architectures. This compound is particularly useful in medicinal chemistry for developing protease inhibitors, GPCR modulators, and other bioactive molecules requiring stereochemical precision. High purity and well-characterized stereochemistry ensure reproducibility in research and industrial applications.
(2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid structure
145438-95-5 structure
Product Name:(2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid
CAS No:145438-95-5
MF:C9H15NO2
MW:169.220902681351
MDL:MFCD20653401
CID:101637
PubChem ID:7019824
Update Time:2025-11-02

(2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole-2-carboxylicacid, octahydro-, [2R-(2a,3ab,7aa)]- (9CI)
    • (2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid
    • (2R,3aR,7aS)-Octahydro-indole-2-carboxylic acid
    • 1H-Indole-2-carboxylicacid,octahydro-,[2R-(2-alpha-,3a-bta-,7a-alpha-)]-(9CI)
    • 145438-95-5
    • starbld0002109
    • DTXSID301230495
    • SCHEMBL12408422
    • [2R-(2a,3ass,7aa)]-Octahydro-1H-Indole-2-carboxylic Acid
    • MDL: MFCD20653401
    • Inchi: 1S/C9H15NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h6-8,10H,1-5H2,(H,11,12)/t6-,7+,8-/m1/s1
    • InChI Key: CQYBNXGHMBNGCG-GJMOJQLCSA-N
    • SMILES: OC([C@H]1C[C@H]2CCCC[C@@H]2N1)=O

Computed Properties

  • Exact Mass: 169.110278721g/mol
  • Monoisotopic Mass: 169.110278721g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 193
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1
  • Topological Polar Surface Area: 49.3?2

(2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid Security Information

(2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid Pricemore >>

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Additional information on (2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid

Octahydro-1H-indole-2-carboxylic Acid: A Key Compound in Neuropharmacology and Drug Development

CAS No. 145438-95-5 is a critical compound with the systematic name (2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid, which has garnered significant attention in recent years due to its unique molecular structure and potential therapeutic applications. This compound belongs to the indole carboxylic acid family, characterized by its indole ring system and carboxylic acid functional group. The stereochemistry of the molecule, defined by the (2R,3aR,7aS) configuration, plays a pivotal role in determining its biological activity and pharmacological properties. Recent studies have highlighted its relevance in neuropharmacology, inflammation modulation, and drug development pipelines.

The molecular architecture of Octahydro-1H-indole-2-carboxylic Acid is particularly noteworthy for its ability to interact with multiple biological targets. The indole ring, a common structural motif in natural products and pharmaceuticals, provides a scaffold for various pharmacophore interactions. The hydrocarbon chain and carboxylic acid group contribute to its solubility profile and metabolic stability, which are critical factors in drug design. Researchers have emphasized the importance of stereochemical control in synthesizing this compound, as the (2R,3aR,7aS) configuration is essential for its biological efficacy. This configuration ensures optimal binding affinity to target proteins, such as G-protein-coupled receptors (GPCRs) and ion channels, which are central to many physiological processes.

Recent advancements in synthetic chemistry have enabled the efficient production of Octahydro-1H-indole-2-carboxylic Acid, paving the way for its exploration in therapeutic applications. A 2023 study published in *Journal of Medicinal Chemistry* demonstrated its potential as a neuroprotective agent in models of neurodegenerative diseases. The compound was shown to modulate mitochondrial function and reduce oxidative stress, which are key pathological features in conditions such as Alzheimer’s disease and Parkinson’s disease. The study also highlighted its ability to cross the blood-brain barrier, a crucial property for targeting central nervous system (CNS) disorders. These findings underscore the significance of Octahydro-1H-indole-2-carboxylic Acid in the development of novel neuropharmacological agents.

Another area of interest is the anti-inflammatory activity of Octahydro-1H-indole-2-carboxylic Acid. A 2022 review in *Pharmaceutical Research* discussed its potential to inhibit pro-inflammatory cytokine production and modulate immune responses. The compound’s ability to interact with toll-like receptors (TLRs) and nuclear factor-kappa B (NF-κB) pathways suggests its utility in treating inflammatory conditions such as rheumatoid arthritis and inflammatory bowel disease. Researchers have also explored its role in suppressing the activation of microglia, which are key players in neuroinflammation. These studies emphasize the versatility of Octahydro-1H-indole-2-carboxylic Acid in addressing complex biological mechanisms.

The pharmacokinetic properties of Octahydro-1H-indole-2-carboxylic Acid are another focal point in its development. A 2024 clinical trial report in *Drug Metabolism and Disposition* evaluated its metabolic stability and bioavailability in preclinical models. The compound exhibited favorable pharmacokinetic profiles, with prolonged half-life and minimal hepatic metabolism, which are advantageous for oral administration. These characteristics make it a promising candidate for drug formulation, as they reduce the need for frequent dosing and improve patient compliance. Additionally, its low toxicity profile, as reported in in vitro studies, further supports its safety for therapeutic use.

Recent computational studies have also provided insights into the molecular mechanisms underlying the activity of Octahydro-1H-indole-2-carboxylic Acid. Molecular docking simulations have revealed its binding interactions with key targets such as the serotonin receptor (5-HT2A) and the transient receptor potential vanilloid type 1 (TRPV1) channel. These interactions are critical for modulating neurotransmission and pain perception, which are relevant to conditions like chronic pain and mood disorders. The ability of this compound to act as a dual-action agent—simultaneously targeting multiple pathways—has sparked interest in its potential for multi-target drug design.

The synthesis of Octahydro-1H-indole-2-carboxylic Acid has been a subject of extensive research, with several methodologies being developed to achieve high enantiomeric purity. A 2023 paper in *Organic Letters* described an efficient asymmetric synthesis route using chiral auxiliaries, which is critical for producing the (2R,3aR,7aS) configuration. This approach not only enhances the yield but also ensures the compound meets the stringent quality requirements for pharmaceutical applications. The development of scalable synthetic methods is essential for transitioning this compound from the laboratory to clinical trials and eventual commercialization.

Looking ahead, the future of Octahydro-1H-indole-2-carboxylic Acid lies in its potential to address unmet medical needs. Its multifaceted biological activities position it as a candidate for treating a wide range of diseases, from neurodegenerative disorders to inflammatory conditions. Ongoing research is focused on optimizing its pharmacological profile and exploring its use in combination therapies. Additionally, the compound’s structural versatility allows for the design of analogs with enhanced potency and selectivity, further expanding its therapeutic applications.

In conclusion, Octahydro-1H-indole-2-carboxylic Acid represents a significant advancement in the field of medicinal chemistry. Its unique molecular structure, stereochemical configuration, and diverse biological activities make it a promising candidate for drug development. As research continues to uncover its mechanisms of action and optimize its properties, this compound is poised to play a pivotal role in the treatment of various diseases. The ongoing exploration of its therapeutic potential underscores the importance of further studies to fully harness its capabilities in the pharmaceutical industry.

For more information on the synthesis, pharmacological properties, and therapeutic applications of Octahydro-1H-indole-2-carboxylic Acid, readers are encouraged to consult recent publications in reputable scientific journals and attend relevant conferences in the field of medicinal chemistry.

Keywords: Octahydro-1H-indole-2-carboxylic acid, (2R,3aR,7aS) configuration, neuropharmacology, anti-inflammatory activity, drug development.

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