cis-(1R,3R)-1,2,3,4-Tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride
[CAS# 171752-68-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: cis-(1R,3R)-1,2,3,4-Tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride
• Synonyms: methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
• Molecular Formula: C₂₀H₁₈N₂O₄.HCl
• Molecular Weight: 386.83
• CAS Registry Number: 171752-68-4
• EC Number: 895-176-6
• SMILES: COC(=O)[C@H]1CC2=C([C@H](N1)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25.Cl

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

Discovery and Applications

cis-(1R,3R)-1,2,3,4-Tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride is a complex organic compound characterized by a fused heterocyclic system combined with a methylenedioxyphenyl substituent. The molecule consists of a tetrahydropyrido[3,4-b]indole core, which is a fused ring system combining a pyridine and an indole ring. The "cis-(1R,3R)" descriptor specifies the relative and absolute stereochemistry at two chiral centers in the molecule, indicating that the substituents at these positions are on the same side in three-dimensional space and have defined stereochemical configurations.

The 3,4-methylenedioxyphenyl group attached to the core structure is a benzene ring with adjacent oxygen atoms connected by a methylene bridge (-O-CH₂-O-), which forms a dioxole ring fused to the aromatic system. This moiety is commonly found in various natural products and synthetic bioactive molecules and is known to influence biological activity, often contributing antioxidant or enzyme-modulating properties.

The carboxylic acid methyl ester group at position 3 of the tetrahydropyridoindole ring adds further chemical functionality. The ester group can influence the compound’s solubility, stability, and interaction with biological targets, as esters are often used as prodrug motifs that may be hydrolyzed enzymatically to release the corresponding acid in vivo.

The hydrochloride form indicates the presence of a protonated nitrogen in the molecule, which forms an ionic salt with chloride ions (Cl⁻). This salt form enhances the compound’s solubility in water and stability, making it more suitable for pharmaceutical applications and biological studies.

Synthetically, this compound can be prepared through multi-step organic synthesis involving the construction of the tetrahydropyrido[3,4-b]indole scaffold, introduction of the 3,4-methylenedioxyphenyl substituent via coupling reactions, and methyl ester formation. Control of stereochemistry at the 1 and 3 positions is achieved through chiral catalysts, resolution techniques, or stereoselective synthetic pathways to yield the cis isomer with (1R,3R) configuration.

This compound belongs to a class of molecules studied for their potential biological and pharmacological activities, often related to their interaction with central nervous system receptors, enzymes, or nucleic acids. The tetrahydropyridoindole framework has been investigated for its neuroactive, anticancer, and enzyme inhibitory properties, while the methylenedioxyphenyl group can modulate these effects through electronic and steric influences.

Physicochemical characterization of this compound includes nuclear magnetic resonance (NMR) spectroscopy to determine its molecular structure and stereochemistry, mass spectrometry for molecular weight confirmation, infrared (IR) spectroscopy for functional group identification, and elemental analysis. Crystallographic studies may also be used to confirm the precise 3D arrangement of atoms and stereochemistry.

In pharmaceutical and biochemical research, the hydrochloride salt is often preferred due to its improved solubility and bioavailability compared to the free base. Its pharmacokinetic and toxicological profiles require thorough evaluation to understand its metabolism, safety, and potential therapeutic applications.

In summary, cis-(1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride is a stereochemically defined heterocyclic compound incorporating a tetrahydropyridoindole core, a biologically relevant methylenedioxyphenyl group, and a methyl ester functionality. The hydrochloride form enhances its solubility and stability, facilitating its use in research related to neuropharmacology and medicinal chemistry.

References

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