Methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
[CAS# 171596-41-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: Methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• Molecular Formula: C₂₀H₁₈N₂O₄
• Molecular Weight: 350.37
• CAS Registry Number: 171596-41-1
• SMILES: COC(=O)[C@H]1CC2=C([C@H](N1)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25

Properties

• Solubility: Insoluble (7.4E^-3 g/L) (25 °C), Calc.^*
• Density: 1.359±0.06 g/cm (20 °C, 760 torr)³ Calc.^*
• Melting point: 154-156 º°C (Expl.)^**
• Boiling point: 531.0±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 274.9±30.1 °C (Calc.)^*
• Index of refraction: 1.664 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

^** Xiao, Sen

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovery and Applications

Methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate is a synthetic organic compound characterized by a fused heterocyclic structure that combines features of a pyridoindole core and a benzodioxole moiety. Its molecular architecture includes a methyl ester functional group attached at the 3-position of the tetrahydro-pyridoindole ring system, with specific stereochemistry defined at the 1R and 3R chiral centers. This compound belongs to a class of molecules often studied for their potential pharmacological and biochemical activities, given the biological relevance of both the indole and benzodioxole frameworks.

The compound’s core structure, the pyrido[3,4-b]indole scaffold, is a fused heterocycle integrating a pyridine ring and an indole moiety. This bicyclic system is part of a larger group of alkaloids and synthetic analogs known for diverse biological effects, including neuroactivity, anticancer properties, and enzyme modulation. The presence of the tetrahydro modification indicates partial saturation of the ring system, which can influence the molecule’s conformational flexibility and interaction with biological targets.

Attached to this core is the 1,3-benzodioxole substituent, a bicyclic aromatic ring system containing a methylene dioxy bridge linking two adjacent oxygen atoms on a benzene ring. Benzodioxole units are found in various natural products and synthetic compounds, often imparting antioxidant, antitumor, or enzyme inhibitory activities. Their incorporation into heterocyclic frameworks enhances the structural complexity and potential functional diversity of the molecules.

The methyl ester group at the 3-position serves both as a chemical handle for synthetic modifications and as a functional group influencing the molecule’s physicochemical properties such as polarity, solubility, and metabolic stability. Esters are also known prodrug motifs, where enzymatic hydrolysis can release active acid forms in biological systems, thus modulating pharmacokinetic profiles.

The stereochemical configuration at the 1R and 3R centers is critical for the biological activity of such molecules, as it affects the three-dimensional shape, binding affinity, and specificity to biological macromolecules such as enzymes, receptors, or nucleic acids. Stereochemistry can also influence the compound’s metabolism and toxicity, necessitating precise control during synthesis and characterization.

Synthesis of methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate generally involves multi-step organic reactions starting from substituted indole or pyridine derivatives. Key synthetic strategies include ring closure reactions to form the fused pyridoindole system, introduction of the benzodioxole ring via aromatic substitution or coupling reactions, and esterification steps to install the methyl carboxylate group. Enantioselective synthesis or resolution methods are employed to obtain the specific stereochemical isomers.

This compound and related derivatives have been investigated in medicinal chemistry research for their potential as central nervous system agents, anticancer drugs, or enzyme inhibitors. The pyridoindole scaffold is known to interact with various biological targets, including monoamine oxidase enzymes, neurotransmitter receptors, and DNA intercalation sites, which may translate into pharmacological effects such as antidepressant, anxiolytic, or antiproliferative activities. The benzodioxole moiety may enhance these effects through additional interactions or modulation of redox states.

Physicochemical characterization of this compound includes techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, infrared spectroscopy, and X-ray crystallography, which confirm the molecular structure, stereochemistry, and purity. These data support further biological evaluation and formulation development.

Due to the presence of multiple functional groups and a complex fused ring system, methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate exhibits distinct solubility profiles, generally being moderately soluble in organic solvents such as methanol, ethanol, and dimethyl sulfoxide (DMSO), which facilitates its use in various in vitro assays.

Toxicological and pharmacokinetic studies are essential to determine the safety profile and metabolic fate of this compound. Given the biological activities associated with its core structures, the compound must be evaluated for potential off-target effects, metabolic stability, and bioavailability to assess its suitability as a drug candidate or biochemical tool.

In summary, methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate is a stereochemically defined heterocyclic ester containing biologically relevant pyridoindole and benzodioxole units. Its synthetic accessibility, structural complexity, and potential biological activities make it a valuable compound for research in medicinal chemistry and pharmacology. Continued studies aim to explore its interactions with biological targets and assess its potential applications in therapeutic development.

References

2004. Tadalafil. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0004