24521-76-4

Basic information

• Product Name: 4-HYDROXY-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE
• Synonyms: 4-HYDROXY-6-MERCAPTOPYRAZOLE(3,4-D)PYRIMIDINE;4-HYDROXY-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE;6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDIN-4-OL;6-MERCAPTO-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-OL;1,5,6,7-tetrahydro-6-thioxo-4H-pyrazolo[3,4-d]pyrimidin-4-one;4-Hydroxy-6-mercaptopyrazolo3,4-düpyrimidine, 98%;4-Hydroxy-6-mercapto-1H-pyrazolo[3,4-d]pyrimidine, 98%;4-Hydroxy-6-mercaptopyrazolo[3,4-d]pyrimidine,98%
• CAS NO: 24521-76-4
• Molecular Formula: C₅H₄N₄OS
• Molecular Weight: 168.18
• EINECS: 246-296-7
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Nucleotides and Nucleosides;Aromatics;Bases & Related Reagents;Nucleotides
• Mol File: 24521-76-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: >310°C
• Boiling Point: 334.3°Cat760mmHg
• Flash Point: 156°C
• Appearance: Light yellow/Crystalline Powder
• Density: 2.08g/cm³
• Vapor Pressure: 6.66E-05mmHg at 25°C
• Refractive Index: 2.019
• Storage Temp.: -20°C Freezer
• Solubility: Aqueous Base (Slightly), DMSO (Slightly)
• PKA: 8.27±0.20(Predicted)
• BRN: 140413
• CAS DataBase Reference: 4-HYDROXY-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE(24521-76-4)
• EPA Substance Registry System: 4-HYDROXY-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE(24521-76-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 24521-76-4(Hazardous Substances Data)

Usage

Chemical Properties

Off White Powder

Uses

4-Hydroxy-6-mercaptopyrazolo[3,4-d]pyrimidine (cas# 24521-76-4) is a compound useful in organic synthesis.

InChI:InChI=1/C5H4N4OS/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)

Upstream product

• 17356-08-0 thiourea 
• 140-89-6 potassium ethyl xanthogenate 
• 5334-31-6 5-amino-1H-pyrazole-4-carboxylic acid amide 
• 27511-79-1 3-amino-4-pyrazolocarboxamide hemisulfate 
• 42754-97-2 6-chloro-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 

Downstream Products

• 5334-32-7 1H-pyrazolo[3,4-d]pyrimidin-4,6-dithione 
• 5444-29-1 6-methylsulfanyl-1⁽²⁾H-pyrazolo[3,4-d]pyrimidin-4-ylamine 
• 85426-79-5 4-chloro-6-methylmercapto-1H-pyrazolo[3,4-d]pyrimidine 
• 55084-74-7 6-methylsulfanyl-1⁽²⁾H-pyrazolo[3,4-d]pyrimidine 
• 877630-72-3 C₁₂H₉ClN₄OS 

Relevant articles and documents

Design and synthesis of novel heterofused pyrimidine analogues as effective antimicrobial agents

A total of 66 novel heterofused pyrimidine analogues (pyrazolo[3,4-d]pyrimidine (7-43) and pyrido[2,3-d]pyrimidine (51a-l & 52a-h)) were synthesized by employing suitable methods. The desired structures of all the synthesized compounds were confirmed based on FT-IR, 1H NMR, 13C NMR and HRMS experimental data. Further, 19F NMR and 1H-15N HMBC of the representative compound were presented. All the final compounds were screened for their in vitro antitubercular (Mycobacterium tuberculosis; H37 Rv), antibacterial (S. aureus, B. subtilis, E. coli and P. aeruginosa) and antifungal (C. neoformans, C. albicans and A. niger) activities. Compounds 51d, 51j, 51k, 51l, and 51g displayed good antibacterial and antifungal activity (MIC = 12.5 μg/ml) against bacterial and fungal strains, while moderate inhibition (MIC = 59 μM) was observed for 51l against H37 Rv strain.

Identification of novel, exosite-binding matrix metalloproteinase-13 inhibitor scaffolds

Matrix metalloproteinase-13 (MMP-13) has been implicated as the protease responsible for collagen degradation in cartilage during osteoarthritis (OA). Compounds that inhibit the metalloproteinase at the Zn binding site typically lack specificity among MMP family members. Analogs of the low-micromolar lead MMP-13 inhibitor 4, discovered through high-throughput screening, were synthesized to investigate structure-activity relationships in this inhibitor series. Systematic modifications of 4 led to the discovery of MMP-13 inhibitors 20 and 24 which are more selective than 4 against other MMPs. Compound 20 is also approximately fivefold more potent as an MMP-13 inhibitor than the original HTS-derived lead compound 4.

Synthesis and biological evaluations of pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 inhibitors

A series of 1,4,6-trisubstituted pyrazolo[3,4-d]pyrimidines 15-19, 30-38 capable of selectively inhibiting CDK2 activity were synthesized by derivatization at C-4, C-6 and N-1 with various amines and lower alkyl groups. For above synthetic compounds, biological evaluation was carried out and structure-activity relationship was examined. In our series, 4-anilino compounds exhibited better CDK2 inhibitory activity and antitumor activity compared to 4-benzyl compounds. The compounds 33a,b having a 3-fluoroaniline group at C-4 showed comparable or superior CDK2 inhibitory activity to those of olomoucine and roscovitine as reference compounds. In general, the unsubstituted compounds (30a,b, 33a,b, 36a,b) at N-1 possessed higher potency than the substituted compounds (32a,b, 34a,b) for the CDK2 inhibitory activity. As for EGFR inhibitory activity, most compounds didnot have a significant activity. The compounds 32a,b exhibited potent cell growth inhibitory activity against human cancer cell lines, but their CDK2 inhibitory activities were slightly poorer than olomoucine.