65973-70-8

Usage

Chemical structure

A pyrazole derivative with a carbonitrile group and an amino group attached to a phenyl ring with a nitro group at the 3-position

Applications in medicinal chemistry

Development of potential drug candidates, studied for its potential as an antiparasitic agent

Potential properties

Antibacterial or antifungal due to the presence of the nitrophenyl group

Pharmacological and medicinal applications

Unique chemical structure and properties

Upstream product

• 123-06-8 Ethoxymethylenemalononitrile 
• 619-27-2 3-nitrophenylhydrazine 
• 99-09-2 3-nitro-aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 
• 51516-96-2 3-nitrophenylhydrazine hydrochloride 

Downstream Products

• 65973-98-0 1-(3-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 16459-43-1 2-(3-nitro-phenyl)-2H-pyrazol-3-ylamine 
• 887472-38-0 C₁₀H₉N₅ 
• 65973-98-0 1-(3-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 65974-01-8 4-chloro-1-(3-nitro-phenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 135108-61-1 4-Amino-5-methyl-1-(3-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 135108-76-8 4-Amino-1-(3-amino-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 

Relevant academic research and scientific papers

Synthesis, in vitro and in vivo anticancer activity of novel 1-(4-imino-1-substituted-1H-pyrazolo[3,4-d]pyrimidin-5(4H)-yl)urea derivatives

A series of pyrazolo[3,4-d]pyrimidine and urea hybrids have been designed, synthesized and evaluated for their anticancer activity in vitro and in vivo cancer models. Among them, compounds 28, 30, 33, 36 and 37 showed promising cytotoxicity against tested cancer cell lines. Compound 37 (CBS-1) appeared as the most active derivative and it exhibited better cytotoxicity against all tested cell lines as compared to doxorubicin. CBS-1 successfully inhibited cell cycle progression and displayed good apoptosis in A549 cells. CBS-1 significantly induced caspase-3 activation and suppressed NF-κB and IL-6 activation in immunocytochemistry, qPCR and western blot analysis. Additionally, CBS-1 prominently displayed tumoricidal effects in lung adenocarcinoma in vivo xenograft nude mice model.

GLUCOSE TRANSPORT INHIBITORS

The present invention relates to chemical compounds of general formula (I): in which RA, RB, RC, RD, m, and n are as given in the description and in the claims, and which effectively and selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

HETEROCYCLIC DERIVATIVES AS IAP BINDING COMPOUNDS

The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, solvates thereof, that bind to Inhibitor of Apoptosis Proteins (IAPs). The compounds of the invention may be used as diagnostic and therapeutic agents in the

Inhibitors of IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: wherein X, Y, A, R1, R2, R3, R4, R4′, R5, R5′, R6 and R6′ are as described herein.

Novel azo dye compound

A compound represented by formula (I): Formula (I) wherein Z1 is atoms necessary for forming an aromatic ring; Z2 is atoms necessary for forming an aromatic hetero ring; V1 and V2 each are a substituent, and at least one of V1 and V2 is a hydroxyl, primary- or secondary- or tertiary-amino, acylamino, or sulfonamido group; r is 1 to 4; s is 1 to 4; the ring formed by Z1 or Z2 may have a substituent other than V1 or V2; M1 is a counter ion; m1 is the number necessary for neutralizing charge; and X1 and X2 each are a carbon or hetero atom, and at least one of X1 and X2 is a hetero atom.

PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS

The present invention relates generally to inhibitors of the kinases and more particularly to novel pyrazolopyrimidine compounds.

Novel pyrazolopyrimidine derivatives as GSK-3 inhibitors

A series of [1-aryl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]arylhydrazones were discovered as novel inhibitors glycogen synthase kinase-3 (GSK-3). Based on initial modeling a detailed SAR was constructed. Modification of the interior binding aryl ring (Ar1) determined this to be a tight binding region with little room for modification. As predicted from the model, a large variety of modifications could be incorporated into the hydrazone aryl ring. This work led to GSK-3 inhibitors in the low nano-molar range.

Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine

Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.