(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester
[CAS 171489-59-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester
• Synonyms: methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• Molecular Formula: C₂₂H₁₉ClN₂O₅
• Molecular Weight: 426.85
• CAS Registry Number: 171489-59-1
• EC Number: 689-794-3
• SMILES: COC(=O)[C@H]1CC2=C([C@H](N1C(=O)CCl)C3=CC4=C(C=C3)OCO4)NC5=CC=CC=C25

Properties

• Density: 1.445
• Melting point: 230-232 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-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
Eye irritation	Eye Irrit.	2	H319

chemBlink Chemical Story

(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester is a complex chemical compound that has attracted attention due to its potential applications in medicinal chemistry. This substance is notable for its unique structural features and its possible implications in drug development.

The discovery of this compound is rooted in the exploration of novel pyridoindole derivatives, which are known for their diverse biological activities. The specific structure of (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester combines several key functional groups that contribute to its chemical properties and biological potential.

The pyrido[3,4-b]indole core is a crucial element of this compound, providing a rigid framework that can be tailored for various biological interactions. This core structure is linked to a benzodioxole moiety, which is known for its role in enhancing the compound’s interaction with biological targets. The benzodioxole group is often associated with increased activity and specificity in medicinal compounds.

The chloroacetyl group attached to the pyridoindole core is another important feature, contributing to the compound's reactivity and potential biological activity. The chloroacetyl group can facilitate the formation of covalent bonds with biological targets, making it a valuable component in drug design for targeting specific proteins or enzymes.

The methyl ester at the carboxylic acid position further modifies the compound’s solubility and bioavailability. Esterification is a common strategy to improve the pharmacokinetic properties of drugs, aiding in their absorption and distribution within the body.

The stereochemistry of the compound, denoted by (1R,3R), is significant as it affects the compound's interaction with biological systems. The chiral centers in the molecule influence its three-dimensional structure, which in turn impacts its binding affinity and activity.

This compound's potential applications are vast. It is being investigated for its possible roles as a therapeutic agent in treating various diseases. The pyridoindole scaffold has been shown to exhibit a range of biological activities, including anti-inflammatory, antitumor, and antimicrobial effects. The incorporation of the benzodioxole and chloroacetyl groups could enhance these properties, offering new avenues for drug development.

Additionally, the compound serves as a valuable research tool in understanding the mechanisms of action of pyridoindole derivatives and their interactions with biological targets. Its complex structure and functional groups make it an interesting subject for further investigation and optimization in the field of medicinal chemistry.

References

2012. Simultaneous determination of diastereoisomeric and enantiomeric impurities in (1R, 3R)‐1‐(1,3‐benzodioxol‐5‐yl)‐2‐(chloroacetyl)‐2,3,4,9‐tetrahydro‐1h‐pyrido[3,4‐b]indole‐3‐carboxylic acid methyl ester a key intermediate of tadalafil by chiral high‐performance liquid chromatography. Chirality.
DOI: https://pubmed.ncbi.nlm.nih.gov/22344859

2010. Introduction of Aminoalkyl Groups. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-110-00164

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