74772-07-9

Usage

Structure

Ethyl ester derivative of 1H-pyrazole-4-carboxylic acid with a methyl group and a nitrophenylamino group

Applications

+ Pharmaceutical research and development (synthesis of potential drug candidates)
+ Synthesis of novel compounds with potential biological activity
+ Development of dyes and pigments (due to the nitrophenylamino group)

Importance

Valuable building block in chemical and pharmaceutical industries.

Upstream product

• 31037-02-2 ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 94-05-3 2-cyano-3-ethoxyacrylic acid ethyl ester 

Downstream Products

• 479232-57-0 (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide 
• 479234-64-5 (4-(aminomethyl)-3-methylphenyl)(1-methyl-3a,4,10,10a-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methanone 
• 479234-62-3 2-methyl-4-(1-methyl-1,3a,4,5,10,10a-hexahydrobenzo[b]-pyrazolo[3,4-e][1,4]diazepine-5-carbonyl)benzonitrile 
• 479234-83-8 1-methyl-1,4,5,10-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepine 
• 749226-94-6 5-(2-amino-phenylamino)-1-methyl-1H pyrazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

Oxytocin (OT) and its receptor (OT-R) are implicated in the etiology of autism spectrum disorders (ASD), and OT-R is a potential target for therapeutic intervention. Very few nonpeptide oxytocin agonists have currently been reported. Their molecular and in vivo pharmacology remain to be clarified, and none of them has been shown to be efficient in improving social interaction in animal models relevant to ASD. In an attempt to rationalize the design of centrally active nonpeptide full agonists, we studied in a systematic way the structural determinants of the affinity and efficacy of representative ligands of the V1a and V2 vasopressin receptor subtypes (V1a-R and V2-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure-affinity and structure-efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration.

VASOPRESSIN V1A ANTAGONISTS

The present invention concerns compounds inter alia according to general formula 1a. Compounds according to the invention are vasopressin V 1a receptor antagonists. Pharmaceutical compositions of the compounds are useful as treatment of dysmenorrhoea.

Piperazines as oxytocin agonists

Disclosed are novel compounds according to general formula I, which have shown OT agonist activity.

Non-peptide oxytocin agonists

The first non-peptide, low molecular weight agonists of the hormone oxytocin (OT) are reported. The most potent compound, 39, showed an EC 50 = 33 nM and was selective for the OT receptor. A library of compounds targeted to the vasopressin/oxytocin family of receptors was screened for activity at a cloned human oxytocin receptor using a reporter gene assay. Potency and selectivity were optimised to afford compound 39, EC50 = 33 nM. This series of compounds represents the first disclosed, non-peptide, low molecular weight agonists of the hormone oxytocin (OT).

Synthesis and Pharmacological Evaluation of a Series of 4-Piperazinylpyrazolo- and -benzodiazepines as Potential Anxiolytics

The synthesis and pharmacological evaluation of a series of pyrazolobenzodiazepines are described.Some of the 4-piperazinyl-2,10-dihydropyrazolobenzodiazepine derivatives demonstrated potent anxiolytic activity in the three-part operan