(S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid RC00156

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:  www.cnroyalchem.com

【  Providing a complete set of intermediates and impurities for Lifitegrast  】

【  Providing a complete set of intermediates and impurities for Lifitegrast  】

【  Providing a complete set of intermediates and impurities for Lifitegrast  】

Product Name:  (S)-2-[(5,7-Dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl)amino]-3-(3-(methylsulfonyl)phenyl)propanoic acid
CAS Number:  851785-70-1
Synonyms:
(S)-2-(5,7-Dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
(S)-N-(5,7-Dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-(3-(methylsulfonyl)phenyl)alaninate

Chemical Structure & Properties

Molecular Formula:  C₂₀H₁₈Cl₂N₂O₅S

Molecular Weight:  469.34 g/mol 

Stereochemistry:  Single enantiomer (S-configuration at the α-carbon of the propanoic acid moiety).

Key Functional Groups:

Dichloro-tetrahydroisoquinoline scaffold (lipophilic, bioactive core).

Sulfonyl group (-SO₂CH₃; strong electron-withdrawing, enhances binding affinity).

Carboxamido linker (-CONH-).

Free carboxylic acid (-COOH; ionizable, enables salt formation).

Chemical Characteristics

Solubility:

Likely soluble in polar organic solvents (e.g., DMSO, DMF), methanol, or ethanol.

Low solubility in water (free acid form).

pKa Estimation:

Carboxylic acid (≈4.0-4.5) and tetrahydroisoquinoline nitrogen (≈7.0-9.0) may confer zwitterionic behavior at physiological pH.

LogP (Predicted):  ~3.0-4.0 (moderate lipophilicity due to aryl/heterocyclic groups).

Potential Applications

Pharmaceutical Research:

Target-specific bioactive compound, potentially for:

Central Nervous System (CNS) disorders  (tetrahydroisoquinoline scaffold is common in neuroactive agents).

Oncology  (dichloro groups may enhance DNA interaction or kinase inhibition).

Inflammation/Immunology  (sulfonyl group is prevalent in COX-2/PDE inhibitors).

Likely functions as a  protease inhibitor ,  receptor antagonist , or  enzyme modulator  due to structural motifs.

Chemical Biology Probe:

Useful for target validation, mechanism-of-action studies, or inhibitor screening.

Medicinal Chemistry:

Key intermediate for SAR (Structure-Activity Relationship) optimization of tetrahydroisoquinoline-based drug candidates.

Handling & Storage

Storage Conditions:

Store at  -20°C or below  under inert atmosphere (argon/nitrogen).

Protect from light and moisture.

Stability:

Stable under recommended storage; avoid strong acids/bases, oxidizing agents.

Handling Precautions:

Use PPE (gloves, goggles) in a fume hood.

Avoid inhalation or skin contact (no toxicity data available; handle as potentially hazardous).

Safety & Regulatory

Toxicity:  No specific data available. Assume toxic and handle cautiously.

Regulatory Status:  For research use only (RUO). Not for diagnostic or therapeutic applications.

Key Notes for Researchers

Chirality Matters: Verify enantiomeric purity (S-configuration is critical for biological activity). 

Solubility Challenges:  Salt formation (e.g., sodium salt) may improve aqueous solubility for assays.

Bioactivity Screening:  Prioritize target classes like GPCRs, ion channels, or kinases.

Structural Uniqueness:  Combines rigid heterocycle with flexible phenylpropanoic acid tail, enabling diverse interactions.