37141-71-2

Upstream product

• 3920-37-4 1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxylic acid 

Downstream Products

• 78208-58-9 1,3-dimethyl-4-nitropyrazole-5-carboxamide 
• 104393-45-5 4-(1,3-dimethyl-7-oxopyrazolo<4,3-d>pyrimidin-5-yl)-N-<2-(dimethylamino)ethyl>benzenesulfonamide 
• 104393-36-4 5-(2-Chloro-4-nitro-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-34-2 4-(1,3-dimethyl-7-oxopyrazolo<4,3-d>pyrimidin-5-yl)benzenesulfonic acid 
• 104393-52-4 4-(3,5-Dimethoxy-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-35-3 1,3-Dimethyl-5-(4-trifluoromethyl-phenyl)-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-33-1 5-(2,4-Dimethoxy-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-51-3 4-(3,4-Dichloro-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-50-2 4-(2-Methoxy-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-32-0 5-(3,4-Dimethoxy-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-27-3 5-(3,5-Dimethoxy-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-41-1 5-(2-Amino-4-chloro-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-48-8 4-(4-Chloro-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-25-1 5-(2-Methoxy-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 

Relevant academic research and scientific papers

N-7 SUBSTITUTED PURINE AND PYRAZOLOPYRIMINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE

The present invention relates to compounds of Formula I: wherein R1, R2, R3, A1, A2, A3, A4, Y1 and Y2 and D have the meaning described herein. The present invention also relates to pharmaceutical compositions comprising such compounds and therapeutic uses thereof.

Nonclassical Pschorr and Sandmeyer reactions in pyrazole series

The diazonium salt derived from 4-amino-N,1,3-trimethyl-N-(3-methyl-1- phenyl-1H-pyrazol-5-yl)-1H-pyrazole-5-carboxamide (14) was reacted with a mixture of CuSO4 and NaCl, with ascorbic acid as an initiator to afford the planar derivative 4,6-dihydro-1,4,6,8-tetramethyl-3- phenyldipyrazolo[3,4-b:4′,3′-d]pyridin-5(3H)-one (16) and its unexpected isomer 4,6-dihydro-3,4,6,8-tetramethyl-1-phenyldipyrazolo[4,3-b: 4′,3′-d]pyridin-5(1H)-one (17), as well as the epimers (3S,4S)- (or (3S,4R)-) and (3S,4S)- (or (3S,4S)-) 4-chloro-2,4-dihydro-1′,3′,5, 5′-tetramethyl-2-phenylspiro[pyrazole-3,4′(1′H)-pyrrolo[3,4-c] pyrazol]-6′(5′H)-one (18a and b, respectively). Epimers 18a and b were converted under basic conditions to 4′-chloro-N,1,3,3′- tetramethyl-1′-phenyl-[4,5′-bi-1H-pyrazole]-5-carboxamide (19). The structures of isomers 16 and 17 determined by single-crystal X-ray analysis are also reported. Linear dichroism (LD) measurements for the above isomers suggest that 17 intercalates into DNA, and 17 exhibited antiproliferation activity against human NCI-H460 pulmonary carcinoma cells.

Synthesis and Structure-Activity Relationships of Pyrazolopyrimidin-7-ones as Adenosine Receptor Antagonists

A series of 21 1,3-dialkylpyrazolopyrimidin-7-ones substituted in the 5-position with various phenyl substituents has been synthesized and found to have affinity for the adenosine A1 receptor.The potency pattern due to substituents of the phenyl ring was found to parallel that found in a previously reported 1,3-dialkyl-8-phenylxanthine series.A quantitative structure-activity relationship was developed between these two series that correctly predicted the potencies of six additional 5-substituted pyrazolopyrimidines that were synthesized during the course of the analysis.With use of the correlation as a guide, one additional 5-phenylpyrazolopyrimidine containing a 4amino>sulfonyl substituent to improve aqueous solubility was prepared.On the basis of the high correlation between adenosine binding affinities of analogously substituted xanthines and pyrazolopyrimidines and the close superposition of the heterocyclic rings and substituents that is apparent from molecular models of these two series (Figure 2), it is hypothesized they fit the receptor in an analogous fashion.