(1S,3S)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
[CAS# 171596-43-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (1S,3S)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• Synonyms: Tadalafil Related Impuirty 6; methyl (1S,3S)-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: 171596-43-3
• SMILES: COC(=O)[C@@H]1CC2=C([C@@H](N1)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• 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.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+351+338-P302+352

Discovery and Applications

(1S,3S)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate is a synthetic compound classified as a β-carboline derivative. Structurally, it features a fused tricyclic ring system consisting of an indole moiety incorporated within a pyrido[3,4-b]indole framework, with a methyl ester group at the 3-position and a benzo[d][1,3]dioxol-5-yl substituent at the 1-position. The stereochemistry is specifically defined as (1S,3S), indicating two stereogenic centers at the 1 and 3 positions of the tetrahydrocarboline core.

This compound belongs to a class of molecules known as β-carbolines, which have been studied for their diverse range of biological activities, including psychoactive, neuroprotective, and cytotoxic properties. The inclusion of a benzo[d][1,3]dioxole group, also known as a methylenedioxyphenyl ring, is a structural motif commonly found in bioactive natural products and pharmaceuticals. It can influence the electronic distribution and metabolic stability of the molecule, potentially affecting receptor binding and bioavailability.

While the specific compound (1S,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate does not appear as an approved drug or widely marketed product, analogs within its structural class have been the focus of pharmacological and medicinal chemistry studies. β-Carboline derivatives are known to interact with various central nervous system targets, including monoamine oxidase (MAO), benzodiazepine receptors, and serotonin receptors. Some compounds in this family have demonstrated antitumor, anticonvulsant, antidepressant, and anxiolytic effects in experimental models.

Research efforts involving synthetic β-carbolines, particularly those with chiral centers and functionalized aromatic groups, often aim to investigate structure-activity relationships (SAR) to optimize biological activity and receptor selectivity. The stereochemistry of such molecules plays a crucial role in their interaction with biological targets, and enantiomeric purity is often essential in preclinical and pharmacological evaluations.

In synthesis, compounds of this type are typically obtained through multistep reactions involving Pictet–Spengler condensation or related strategies to construct the tricyclic ring system, followed by functional group modifications to introduce ester and aryl substituents. Chiral catalysts or enantiomerically enriched starting materials may be used to control the stereochemistry at the 1 and 3 positions.

In summary, (1S,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate is a chiral, polycyclic synthetic β-carboline compound with structural features commonly associated with bioactivity in neuropharmacology and oncology research. While not widely marketed or clinically used, it represents a class of molecules with significant interest in medicinal chemistry due to its structural complexity and potential pharmacological applications.

References

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DOI: 10.1016/j.ejmech.2021.113536

2020. Stereoselective Covalent Inhibitors of T-Cell Activation. Synfacts, 16(12).
DOI: 10.1055/s-0040-1719565

2020. Design, synthesis and bio-evaluation of C-1 alkylated tetrahydro-β-carboline derivatives as novel antifungal lead compounds. Bioorganic & Medicinal Chemistry Letters, 30(3).
DOI: 10.1016/j.bmcl.2019.126869