(1S,2R,3S,4R)-4-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-1,2,3-cyclopentanetriol

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 】

Here is a detailed product description for the compound specified by CAS 220347-05-7 and the IUPAC name   (1S,2R,3S,4R)-4-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-1,2,3-cyclopentanetriol :

1. Chemical Identification

CAS Number:  220347-05-7

IUPAC Name:  

(1S,2R,3S,4R)-4-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-1,2,3-cyclopentanetriol

Synonyms:

(1S,2R,3S,4R)-4-({7-[((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino]-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl})cyclopentane-1,2,3-triol

Structurally related analogs may exist under research codes (e.g., early development candidates).

2. Structural Features & Significance

Core Scaffold:  3H-[1,2,3]Triazolo[4,5-d]pyrimidine (a purine isostere mimicking adenine in ATP).

Key Substituents:

5-Position:  Propylthio (-S-CH₂CH₂CH₃) group – enhances lipophilicity/target binding.

7-Position:  Chiral trans-2-(3,4-Difluorophenyl)cyclopropylamine substituent – critical for target specificity and potency; the 3,4-difluorophenyl enhances metabolic stability and binding affinity.

3-Position:  Chiral (1S,2R,3S,4R)-4-hydroxycyclopentylmethyl group – the cyclopentane triol mimics ribose conformation in nucleosides, influencing pharmacodynamics and solubility.

Stereochemistry:  Contains  multiple defined stereocenters  crucial for biological activity:

Cyclopropane: (1R,2S)

Cyclopentane Triol: (1S,2R,3S,4R)

CAUTION:  Synthesis requires strict stereocontrol; enantiomers/diastereomers likely have reduced/inactive activity.

3. Physicochemical Properties (Typical for Class)

Physical State:  Solid (likely amorphous or crystalline powder).

Solubility:  Low water solubility (logP likely >2); soluble in DMSO, DMF, methanol, ethanol.

Stability:  Handle under inert atmosphere; susceptible to oxidation (thioether), photodegradation, acid/base hydrolysis. Store at -20°C. 

Molecular Weight:  ~546.57 g/mol (exact mass calculated).

4. Biological Relevance & Potential Applications

Target Class:  Primarily designed as a  potent and selective kinase inhibitor . The adenine-mimetic scaffold targets ATP-binding pockets.

Indications (Hypothetical/Research Focus):

Oncology (targeting specific kinases in cancer pathways).

Inflammation/Autoimmune Diseases (targeting kinases like JAK, SYK).

Cardiovascular Diseases (targeting kinases like PKA, PKG).

Mechanism:  Competitive ATP antagonism, inhibiting phosphorylation and downstream signaling.

Pharmacological Advantages:

High kinase selectivity conferred by the chiral cyclopropylamino group.

Improved metabolic stability from fluorinated aryl group.

Triol moiety enhances solubility/polar interactions relative to simpler alkyl groups.

5. Research Use

Primary Application:   Biochemical research tool  for studying specific kinase-dependent signaling pathways.

Drug Discovery Stage:  Likely a  preclinical candidate/hit-to-lead compound  – requires extensive ADMET/PK studies.

6. Handling & Safety

Classification:   For Research Use Only . Not for human or veterinary diagnostic/therapeutic use.

Handling:  Use PPE (gloves, lab coat, eye protection). Handle in a well-ventilated fume hood. Avoid dust formation.

Storage:  Store desiccated at -20°C under inert gas (Ar/N₂). Protect from light and moisture.

Safety Data:  Specific toxicological data unavailable. Treat as  potentially hazardous  (may exhibit kinase inhibitor-related toxicity). Consult SDS if available.

7. Significance in Medicinal Chemistry
Represents an advanced  structure-based drug design (SBDD)  effort featuring:

Purine Mimicry:  Triazolopyrimidine core for ATP-site binding.

Stereochemical Optimization:  Precise chirality for target engagement.

Balanced Lipophilicity:  Propylthio vs. triol groups modulate logP and membrane permeability.

Metabolic Stabilization:  Difluorophenyl group reduces oxidative metabolism.

Conformational Restriction:  Cyclopropyl linker enhances potency/selectivity.