74772-07-9

Basic information

• Product Name: 1H-Pyrazole-4-carboxylic acid, 1-methyl-5-[(2-nitrophenyl)amino]-, ethyl ester
• Synonyms: 1-Methyl-5-(2-nitro-phenylamino)-1H-pyrazole-4-carboxylic acid ethyl ester;1-methyl-5-(2-nitro-anilino)-1H-pyrazole-4-carboxylic acid ethyl ester
• CAS NO: 74772-07-9
• Molecular Formula: C13H14N4O4
• Molecular Weight: 290.279
• Mol File: 74772-07-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 66 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 445.5±40.0 °C(Predicted)
• Density: 1.36±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Pyrazole-4-carboxylic acid, 1-methyl-5-[(2-nitrophenyl)amino]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-4-carboxylic acid, 1-methyl-5-[(2-nitrophenyl)amino]-, ethyl ester(74772-07-9)
• EPA Substance Registry System: 1H-Pyrazole-4-carboxylic acid, 1-methyl-5-[(2-nitrophenyl)amino]-, ethyl ester(74772-07-9)

Safety Data

• Hazardous Substances Data: 74772-07-9(Hazardous Substances Data)

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

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

Downstream Products

• 479234-83-8 1-methyl-1,4,5,10-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepine 
• 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 
• 479234-64-5 (4-(aminomethyl)-3-methylphenyl)(1-methyl-3a,4,10,10a-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methanone 
• 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 
• 749226-94-6 5-(2-amino-phenylamino)-1-methyl-1H pyrazole-4-carboxylic acid ethyl ester 

Relevant articles and documents

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.

Piperazines as oxytocin agonists

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

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