35877-38-4

Upstream product

• 35877-37-3 1-benzyl-5-(2,2-diethoxyethyl)-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one 
• 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 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 555-96-4 Benzylhydrazine 
• 1073-62-7 N-benzylhydrazine hydrochloride 

Downstream Products

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

Relevant academic research and scientific papers

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.

Selective synthesis of 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.

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.

Discovery and hit-to-lead optimization of pyrrolopyrimidines as potent, state-dependent Nav1.7 antagonists

Herein we describe the discovery, optimization, and structure-activity relationships of novel potent pyrrolopyrimidine Nav1.7 antagonists. Hit-to-lead SAR studies of the pyrrolopyrimidine core, head, and tail groups of the molecule led to the identification of pyrrolopyrimidine 48 as exceptionally potent Nav1.7 blocker with good selectivity over hERG and improved microsomal stability relative to our hit molecule and pyrazolopyrimidine 8 as a promising starting point for future optimization efforts.

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.

PYRAZOLOPYRIMIDINES AS ANTI - HEPATITS C AGENTS

Pyrazolopyrimidine derivatives of formula (I), or a pharmaceutically acceptable salt thereof, are found to be active against hepatitis C infection, wherein: R1 is C6-C10 aryl, 5- to 10- membered heteroary1, -(C1-C4 alkyl)-(C6-C10 aryl) or -(C1-C4 alkyl)-(5- to 10- membered heteroaryl); R2 is a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10- membered heterocyclyl moiety, said moiety being optionally fused to a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10-membered heterocyclic ring; and X is -NR'-, -NR'-CO-NR''-, -NR'-L, or -NR'-CO-L-, wherein R' and R'' are the same or different and each represent hydrogen or a C1-C6 alkyl group and L represents a C1-C6 alkylene group, the aryl, heteroaryl, heterocyclyl. and carbocyclyl moieties in the R1 and R2 substituents being unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4 alkyl C1-C4alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, nitro, C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heterocyclyl, 5- to 10- membered heteroaryl, -NR'-CO2-R'', -CO2R'', -COR'''-NR'-CO-R''',-CONR'R'',SO2NR'R'',SO2R'''and -O-(CH2)n-R''' substituents, wherein n is from 0 to 4, each R’is the same or different and is hydrogen or C1-C6 alkyl, each R'' is the same or different and is hydrogen, C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, each R''' is the same or different and is C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, and each R'''' is the same or different and is C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heterocryl, the aryl, heteroaryl, heterocyclyl and carbocyclyl moieties in said substituents being unsubstituted or substituted by a further substituent selected from C1-C4 alkyl, C1-C4 hydroxyalkyl and C1-C4 haloalkyl groups.

Synthesis and plant growth regulating activity of new triazolo- and pyrazolopyrimidine derivatives of aminomethyl-, aminoalkyloxymethyl dimethylphosphine oxides and (aminomethane)phosphonic acid esters

New triazolo[4,5-d]pyrimidine and pyrazolo[3,4-d]pyrimidine derivatives of aminomethyl- and aminomethyloxymethyl dimethylphosphine oxides 8-14 as well as of esters of (aminomethane) phosphonic acid 18-20 were synthesized. The structure of the compounds prepared was confirmed by means of elemental analysis, IR, 1H- and 31P{1H}-NMR spectroscopy. Tertiary phosphine oxides 8, 9 and 12 as well as phosphonate 20 showed herbicidal and plant growth regulating activity.