7400-05-7

Basic information

• Product Name: 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE
• Synonyms: NSC 59249;4(1H)-PyriMidinone, 6-aMino-5-(2,2-diethoxyethyl)-2,3-dihydro-2-thioxo-;6-amino-5-(2,2-diethoxyethyl)-2-sulfanylidene-1H-pyrimidin-4-one;6-AMINO-5-(2,2-DIETHOXYETHYL)-2-MERCAPTOPYRIMIDIN-4-OL;6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE;6-AMino-5-(2,2-diethoxyethyl)-2,3-dihydro-2-thioxo-4(1H)-pyriMidinone
• CAS NO: 7400-05-7
• Molecular Formula: C₁₀H₁₇N₃O₃S
• Molecular Weight: 259.33
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Intermediates;Nucleotides;Sulfur & Selenium Compounds;Amines;Aromatics;Heterocycles
• Mol File: 7400-05-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: >300°C
• Appearance: White crystalline solid
• Density: 1.27
• Refractive Index: 1.578
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Methanol
• PKA: 8.08±0.25(Predicted)
• Stability: Sensitive to Aqueous Acid
• CAS DataBase Reference: 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE(7400-05-7)
• EPA Substance Registry System: 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE(7400-05-7)

Safety Data

• Statements: 22-40
• Safety Statements: 36/37
• Hazardous Substances Data: 7400-05-7(Hazardous Substances Data)

Usage

Description

6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE is a white crystalline solid that serves as an intermediate in the production of thymidine phosphorylase inhibitors. These inhibitors play a crucial role in various biological and pharmaceutical applications, particularly in the development of therapeutic agents for cancer treatment.

Uses

Used in Pharmaceutical Industry:
6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE is used as an intermediate for the synthesis of thymidine phosphorylase inhibitors for the pharmaceutical industry. The application reason is that these inhibitors can potentially be developed into therapeutic agents for the treatment of cancer, as they target key enzymes involved in the regulation of thymidine metabolism, which is often dysregulated in cancer cells.
Used in Research and Development:
In the research and development sector, 6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE is used as a key compound for the development of novel thymidine phosphorylase inhibitors. The application reason is to explore the potential of these inhibitors in cancer therapy and to understand their mechanism of action, which can lead to the discovery of more effective and targeted treatments for various types of cancer.
Used in Chemical Synthesis:
6-AMINO-5(2,2-DIETHOXYETHYL)-4-HYDROXY-2-MERCAPTOPYRIMIDINE is also used as a building block in the chemical synthesis of various compounds with potential applications in different industries, such as pharmaceuticals, agrochemicals, and materials science. The application reason is its unique chemical structure, which allows for further functionalization and modification to create new molecules with desired properties and functionalities.

InChI:InChI=1/C10H17N3O3S/c1-3-15-7(16-4-2)5-6-8(11)12-10(17)13-9(6)14/h7H,3-5H2,1-2H3,(H4,11,12,13,14,17)

Upstream product

• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 17356-08-0 thiourea 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 

Downstream Products

• 3680-71-5 7-deazahypoxanthine 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 271-70-5 7H-pyrrolo[2,3-d]pyrimidine 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 156124-78-6 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1440537-02-9 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythropentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine 
• 1252858-45-9 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 1338072-82-4 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidine 
• 169516-55-6 4-chloro-7-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 1536110-54-9 4-methyl-N7-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 29914-75-8 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 480439-89-2 4-chloro-5-iodo-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

NEW COMPOUND HAVING FGFR INHIBITORY ACTIVITY AND PREPARATION AND APPLICATION THEREOF

The present invention relates to a new compound having an FGFR inhibitory activity and preparation and application thereof. In particular, the compound according to the present invention has a structure as shown in formula I, wherein each group and substituent are as defined in the description. Also disclosed in the present invention are a preparation method for the compound and a use thereof in preparation of a drug for treating and/or preventing a tumor-related disease and/or an FGFR-related disease.

Targeting conserved water molecules: Design of 4-aryl-5-cyanopyrrolo[2,3-d] pyrimidine Hsp90 inhibitors using fragment-based screening and structure-based optimization

Inhibitors of the Hsp90 molecular chaperone are showing promise as anti-cancer agents. Here we describe a series of 4-aryl-5-cyanopyrrolo[2,3-d] pyrimidine ATP competitive Hsp90 inhibitors that were identified following structure-driven optimization of purine hits revealed by NMR based screening of a proprietary fragment library. Ligand-Hsp90 X-ray structures combined with molecular modeling led to the rational displacement of a conserved water molecule leading to enhanced affinity for Hsp90 as measured by fluorescence polarization, isothermal titration calorimetry and surface plasmon resonance assays. This displacement was achieved with a nitrile group, presenting an example of efficient gain in binding affinity with minimal increase in molecular weight. Some compounds in this chemical series inhibit the proliferation of human cancer cell lines in vitro and cause depletion of oncogenic Hsp90 client proteins and concomitant elevation of the co-chaperone Hsp70. In addition, one compound was demonstrated to be orally bioavailable in the mouse. This work demonstrates the power of structure-based design for the rapid evolution of potent Hsp90 inhibitors and the importance of considering conserved water molecules in drug design.

THERAPEUTIC AGENTS

The invention provides a compound of formula (I): wherein R1, and W have any of the values defined in the application; or a salt thereof. The compounds and salts thereof have beneficial therapeutic properties (e.g. immunosuppressant properties).