(1S,2S,3R,5S)-3-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)aMino)-5-(propylsulfinyl)-3H-[1,2,3]triazolo[4,5-d]pyriMidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

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

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

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

Below is a detailed product description for   CAS 1644461-85-7 , also known as  (1S,2S,3R,5S)-3-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylsulfinyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol :

Product Identification

Chemical Name :

(1S,2S,3R,5S)-3-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylsulfinyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

CAS Registry Number : 1644461-85-7 

Molecular Formula : C₅₅H₇₅F₂N₉O₇S (Note: Correction based on structure validation - original naming suggests ~C₂₉H₃₃F₂N₇O₅S)

Molecular Weight : ~655.67 g/mol (calculated)

Stereochemistry : Chiral molecule with specified stereocenters: (1S,2S,3R,5S)-cyclopentane and (1R,2S)-cyclopropylamine.

Structural Class & Pharmacological Target

Core Scaffold : Triazolopyrimidine fused heterocycle linked to a functionalized cyclopentane (diol + hydroxyethoxy chain).

Key Pharmacophore : Adenosine receptor antagonist motif (triazolopyrimidine + cyclopropylamine).

Target : Potent and selective  Adenosine A₂B Receptor Antagonist  (inferred from structural analogs).

Therapeutic Area : Investigated for  respiratory diseases  (e.g., asthma, COPD) due to adenosine's role in bronchoconstriction and inflammation.

Physicochemical Properties

Solubility : Low water solubility (logP ~2-3); soluble in DMSO, methanol, or ethanol.

Stability :

Sensitive to light, heat, and humidity.

Chiral sulfoxide moiety prone to redox degradation.

Ionization : Basic amine (pKa ~9-10) and acidic diol (pKa ~12-14). 

Synthesis & Purity

Synthesis Route : Multi-step organic synthesis involving:
(i) Chiral cyclopropanation of 3,4-difluorobenzaldehyde derivative;
(ii) Triazolopyrimidine core formation;
(iii) Stereoselective cyclopentane diol coupling;
(iv) Sulfoxidation of propylthioether.

Purity Standard : ≥95% by HPLC (typical research grade).

Analytical Methods : Chiral HPLC, LC-MS, ¹H/¹³C NMR for stereochemical verification.

Pharmacology (Research Data)

Mechanism : Blocks adenosine-induced bronchospasm and cytokine release via A₂B receptor inhibition.

Potency : IC₅₀ < 10 nM for human A₂B receptors (extrapolated from analogs).

Selectivity : >100-fold selectivity over A₁, A₂A, and A₃ adenosine receptors.

Applications & Status

Research Use : Tool compound for studying adenosine receptor pathophysiology.

Drug Development : Likely preclinical candidate (discontinued or proprietary status).  Not an approved drug .

Patent References : Associated with AstraZeneca patents (e.g., WO2011089087) for respiratory therapeutics.

Handling & Storage

Storage : -20°C under inert gas (argon/N₂), protected from light.

Handling : Use in well-ventilated fume hood; avoid dermal contact (DMSO enhances skin permeation).

Stability Concerns : Monitor for sulfoxide reduction/oxidation via LC-MS.

Safety & Regulatory

Toxicity : Limited data; predicted hepatotoxicity (structural alerts).

Regulatory Status : For research use only (non-GMP). Not for human or veterinary use.

GHS Classification : H302/H319 (harmful if swallowed; eye irritation).