35877-38-4

Basic information

• Product Name: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-1-(phenylmethyl)-
• CAS NO: 35877-38-4
• Molecular Formula: C12H9ClN4
• Molecular Weight: 244.683
• Mol File: 35877-38-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-1-(phenylmethyl)-(35877-38-4)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-1-(phenylmethyl)-(35877-38-4)

Safety Data

• Hazardous Substances Data: 35877-38-4(Hazardous Substances Data)

Upstream product

• 35877-37-3 1-benzyl-5-(2,2-diethoxyethyl)-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 555-96-4 Benzylhydrazine 
• 1073-62-7 N-benzylhydrazine hydrochloride 
• 100-39-0 benzyl bromide 
• 5399-92-8 4-chloro-1H-pyrazolo[3,4-d]pyrimidine 
• 315-30-0 4-hydroxypyrazolo(3,4-d)pyrimidine 
• 20570-96-1 benzylhydrazine dihydrochloride 

Downstream Products

• 1018830-63-1 C₁₆H₁₉N₄O₃P 
• 1365626-42-1 C₂₁H₂₂N₆OS 
• 56156-23-1 1-benzyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-thione 

Relevant articles and documents

Discovery of novel allopurinol derivatives with anticancer activity and attenuated xanthine oxidase inhibition

A series of pyrazolo[3,4-d]pyrimidine derivatives related to allopurinol has been synthesized and evaluated for its cytotoxicity against a panel of three cancer cell lines as well as its xanthine oxidase (XOD) inhibitory activities. Among them, compound 4 showed potent cytotoxicity with IC50 values of 25.5 and 35.2 μM against human hepatoma carcinoma cell lines, BEL-7402 and SMMC-7221, respectively. The anticancer activity of 4 was comparable to that of Tanespimycin (17-N-allylamino-17-demethoxy geldanamycin, 17-AAG) that inhibited the growth of BEL-7402 and SMMC-7221 cells at IC50 values of 12.4 and 9.85 μM, respectively. However, unlike allopurinol, which is also a strong inhibitor of XOD, compound 4 is a much weaker XOD inhibitor, suggesting that the anticancer activities of the allopurinol derivatives may not be associated with XOD inhibition. Moreover, the cytotoxicity of 4 toward normal cells is significantly lower than that of 17-AAG, making 4 a promising lead compound for further optimization of structure-activity relationships that may lead to anticancer agents of clinical utility.

Synthesis of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines from 4,6-dichloropyrimidine-5-carboxaldehyde: Insights into selectivity and reactivity

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with both aromatic and aliphatic hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective, high-yielding, and operationally simple manner are presented. For aromatic hydrazines, the reaction is performed at a high temperature in the absence of an external base. For aliphatic hydrazines, the reaction proceeds at room temperature in the presence of an external base. The observed selectivity and reactivity trends are rationalized through consideration of the proposed reaction mechanism. The 1-substituted 4-chloropyrazolo[3,4-d]pyrimidine products serve as versatile synthetic intermediates, through further functionalization of the 4-chloride moiety, enabling the rapid generation of a structurally diverse array of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines. Georg Thieme Verlag Stuttgart. New York.

A one step synthesis of 1-alkylpyrazolo[5,4-d]pyrimidines

A new synthesis of 1-alkylpyrazolo[5,4-d]pyrimidines is described. The reaction of 4,6-dichloropyrimidine-5-carbaldehyde with various substituted hydrazines provides such compounds in a single step from commercially available starting materials. This method has advantages over methods currently described in the literature for the construction of such ring systems.