5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate
[CAS# 239463-85-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate
• Synonyms: 3-[5-[(2R)-2-aminopropyl]-7-cyano-2,3-dihydroindol-1-yl]propyl benzoate;(2R,3R)-2,3-dihydroxybutanedioic acid
• Molecular Formula: C₂₂H₂₅N₃O₂.C₄H₆O₆
• Molecular Weight: 513.55
• CAS Registry Number: 239463-85-5
• EC Number: 688-292-1
• SMILES: C[C@H](CC1=CC2=C(C(=C1)C#N)N(CC2)CCCOC(=O)C3=CC=CC=C3)N.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate is a chemical compound that has garnered interest in the field of medicinal chemistry due to its complex molecular structure and potential biological activity. The compound consists of an indole ring system, which is a key feature in many biologically active compounds, combined with various functional groups, including a benzoyloxypropyl group and an aminopropyl group. This combination of structural elements suggests that the compound may possess diverse pharmacological properties, particularly in the realm of receptor modulation and enzyme inhibition.

The discovery of 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate is part of ongoing research aimed at identifying new drug candidates for treating a variety of diseases. The indole scaffold has been widely studied for its ability to interact with various biological targets, including neurotransmitter receptors, kinases, and enzymes involved in cellular signaling pathways. The additional functional groups in this compound enhance its ability to engage with specific targets, making it a promising candidate for further investigation.

One of the potential applications of this compound lies in its ability to interact with neurotransmitter receptors, particularly those involved in central nervous system functions. The aminopropyl group, a nitrogen-containing side chain, could facilitate interactions with receptors such as adrenergic, serotonergic, or dopaminergic receptors, which are involved in mood regulation, cognition, and motor control. Given the structure of this compound, it could serve as a lead for the development of new treatments for neurological disorders such as depression, anxiety, or Parkinson’s disease.

Another area of interest for 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate is its potential to act as an enzyme inhibitor. The benzoyloxypropyl group and the nitrile moiety in the structure are known to interact with enzymes, potentially inhibiting their activity. Enzymes are crucial in many biological processes, including those involved in cancer, inflammation, and metabolic disorders. As such, this compound could be explored as a potential therapeutic agent for these conditions, particularly if it can be optimized for selectivity and potency in enzyme inhibition.

Furthermore, the presence of the (2R,3R)-2,3-dihydroxybutanedioate group in the structure indicates that this compound could have applications in chirality-based drug design. Chiral molecules often exhibit different pharmacological properties depending on their stereochemistry. The (2R,3R)-configuration suggests that this compound may have unique interactions with biological receptors and enzymes, making it a valuable candidate for further study in the context of stereochemical effects on drug efficacy.

The versatility of 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate makes it a promising lead compound for drug discovery. Its ability to target a range of biological pathways, including neurotransmitter receptors and enzymes, opens up multiple therapeutic avenues. Future research focused on understanding its biological activity, pharmacokinetics, and optimization for specific targets will be crucial in determining its clinical potential.

References

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