741713-37-1

Basic information

• Product Name: Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)-
• Synonyms: Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)-;(4-Amino-2-(ethylthio)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone
• CAS NO: 741713-37-1
• Molecular Formula: C₁₄H₁₃F₂N₃O₂S
• Molecular Weight: 325.3337264
• Mol File: 741713-37-1.mol

Chemical Properties

• Boiling Point: 545.704°C at 760 mmHg
• Flash Point: 283.832°C
• Appearance: /
• Density: 1.412g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• PKA: 1?+-.0.10(Predicted)
• CAS DataBase Reference: Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)-(741713-37-1)
• EPA Substance Registry System: Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)-(741713-37-1)

Safety Data

• Hazardous Substances Data: 741713-37-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)is used as an anticancer drug for the treatment of non-small cell lung cancer, specifically in patients with ALK-positive metastatic cases. It is effective in blocking the ALK protein, which plays a crucial role in the growth and spread of cancer cells, thereby inhibiting tumor progression and improving patient outcomes.
Used in Clinical Trials:
Alectinib is utilized in clinical trials to evaluate its efficacy and safety in treating non-small cell lung cancer. These trials help determine the optimal dosage, administration methods, and potential side effects, contributing to the development of effective treatment strategies for patients with ALK-positive metastatic non-small cell lung cancer.
Used in Drug Formulation:
Methanone, [4-aMino-2-(ethylthio)-5-pyriMidinyl](2,3-difluoro-6-Methoxyphenyl)is used in the formulation of oral dosage forms such as capsules or tablets for the convenient and effective administration of the drug to patients. This allows for better patient compliance and improved treatment outcomes in the management of non-small cell lung cancer.

InChI:InChI=1/C14H13F2N3O2S/c1-3-22-14-18-6-7(13(17)19-14)12(20)10-9(21-2)5-4-8(15)11(10)16/h4-6H,3H2,1-2H3,(H2,17,18,19)

Upstream product

• 741712-36-7 4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide 
• 202865-58-5 1-bromo-4,5-difluoro-2-methoxybenzene 
• 89853-87-2 4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid 

Downstream Products

• 741713-38-2 (4-aminosulfonylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone 
• 741713-40-6 Ro 4584820 

Relevant articles and documents

Discovery of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5- yl](2,3-difluoro-6-methoxyphenyl)methanone (R547), a potent and selective cyclin-dependent kinase inhibitor with significant in vivo antitumor activity

The cyclin-dependent kinases (CDKs) and their cyclin partners are key regulators of the cell cycle. Since deregulation of CDKs is found with high frequency in many human cancer cells, pharmacological inhibition of CDKs with small molecules has the potential to provide an effective strategy for the treatment of cancer. The 2,4-diamino-5-ketopyrimidines 6 reported here represent a novel class of potent and ATP-competitive inhibitors that selectively target the cyclin-dependent kinase family. This diaminopyrimidine core with a substituted 4-piperidine moiety on the C2-amino position and 2-methoxybenzoyl at the C5 position has been identified as the critical structure responsible for the CDK inhibitory activity. Further optimization has led to a good number of analogues that show potent inhibitory activities against CDK1, CDK2, and CDK4 but are inactive against a large panel of serine/threonine and tyrosine kinases (Ki > 10 μM). As one of these representative analogues, compound 39 (R547) has the best CDK inhibitory activities (Ki = 0.001, 0.003, and 0.001 μM for CDK1, CDK2, and CDK4, respectively) and excellent in vitro cellular potency, inhibiting the growth of various human tumor cell lines including an HCT116 cell line (IC50 = 0.08 μM). An X-ray crystal structure of 39 bound to CDK2 has been determined in this study, revealing a binding mode that is consistent with our SAR. Compound 39 demonstrates significant in vivo efficacy in the HCT116 human colorectal tumor xenograft model in nude mice with up to 95% tumor growth inhibition. On the basis of its superior overall profile, 39 was chosen for further evaluation and has progressed into Phase I clinical trial for the treatment of cancer.