154594-16-8

Basic information

• Product Name: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)
• Synonyms: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI);4-(4-HYDRAZINOPHENYL)-1,2,4-TRIAZOLEHYDROCHLORIDE;4H-1,2,4-Triazole,4-(4-hydrazinylphenyl)-;4-(4-hydrazinylphenyl)-4H-1,2,4-triazole;4-(4-Hydrazinophenyl)-4H-1,2,4-triazole
• CAS NO: 154594-16-8
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.19
• Product Categories: HYDRAZINE
• Mol File: 154594-16-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 410.1°C at 760 mmHg
• Flash Point: 201.8°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 6.16E-07mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: 2-8°C
• PKA: 4.88±0.30(Predicted)
• CAS DataBase Reference: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)(154594-16-8)
• EPA Substance Registry System: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)(154594-16-8)

Safety Data

• Hazardous Substances Data: 154594-16-8(Hazardous Substances Data)

Usage

General Description

4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI) is a chemical compound with the molecular formula C7H8N6. It is a triazole derivative with a hydrazinophenyl group attached to the 4-position of the triazole ring. 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI) has potential applications in pharmaceutical and agricultural industries, as it can act as a building block for the synthesis of various bioactive molecules, including pharmaceutical drugs and agrochemicals. It has also been studied for its potential use in the development of new materials and as a catalyst in organic reactions. Moreover, its structural properties make it a valuable candidate for further research in the fields of medicinal chemistry and drug discovery.

InChI:InChI=1/C8H9N5/c9-12-7-1-3-8(4-2-7)13-5-10-11-6-13/h1-6,12H,9H2

Upstream product

• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 52761-74-7 4-(4-aminophenyl)-4H-1,2,4-triazole 
• 154594-15-7 N-(4-(4H-1,2,4-triazole-4-yl)phenyl)acetamide 

Downstream Products

• 177945-83-4 1-{3-[5-(1,2,4-Triazol-4-yl)-1H-indol-3-yl]propyl}-4-[(benzylamino)methyl]piperidine 
• 174609-14-4 4-Benzyl-1-(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)piperidine Hydrogen Oxalate 

Relevant articles and documents

Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1- yl)ethyl]indoles: Potent agonists for the h5-HT(1D) receptor with high selectivity over the h5-HT(1B) receptor

The design, synthesis, and biological evaluation of a novel series of 3- [2-(pyrrolidin-1-yl)ethyl]-indoles with excellent selectivity for h5-HT(1D) (formerly 5-HT(1Dα)) receptors over h5-HT(1B) (formerly 5-HT(1Dβ)) receptors are described. Clinically effective antimigraine drugs such as Sumatriptan show little selectivity between h5-HT(1D) and h5-HT(1B) receptors. The differential expression of h5-HT(1D) and h5-HT(1B) receptors in neural and vascular tissue prompted an investigation of whether a compound selective for the h5-HT(1D) subtype would have the same clinical efficacy but with reduced side effects. The pyrrolidine 3b was initially identified as having 9-fold selectivity for h5-HT(1D) over h5-HT(1B) receptors. Substitution of the pyrrolidine ring of 3b with methylbenzylamine groups gave compounds with nanomolar affinity for the h5-HT(1D) receptor and 100-fold selectivity with respect to h5-HT(1B) receptors. Modification of the indole 5-substituent led to the oxazolidinones 24a,b with up to 163-fold selectivity for the h5-HT(1D) subtype and improved selectivity over other serotonin receptors. The compounds were shown to be full agonists by measurement of agonist-induced [35S]GTPγS binding in CHO cells expressed with h5-HT receptors. This study suggests that the h5-HT(1D) and h5-HT(1B) receptors can be differentiated by appropriate substitution of the ligand in the region which binds to the aspartate residue and reveals a large binding pocket in the h5-HT(1D) receptor domain which is absent for the h5-HT(1B) receptor. The compounds described herein will be important tools to delineate the role of h5-HT(1D) receptors in migraine.

Indoline and azaindoline derivatives as 5-HT1D alpha receptor agonists

Compounds of formula (I), or a salt or prodrug thereof, wherein Z represents an optionally substituted five-membered heteroaromatic ring selected from furan, thiophene, pyrrole, oxazole, thiazole, isoxazole, isothiazole, imidazole, pyrazole, oxadiazole, thiadiazole, triazole, and tetrazole; E represents a chemical bond or a straight or branched alkylene chain containing from 1-4 carbon atoms; Q represents a straight or branched alkylene chain containing from 1-6 carbon atoms; T represents nitrogen or CH; R1 represents aryl(C1-6)alkyl or heteroaryl(C1-6)alkyl, either of which groups may be optionally substituted; and R2 represents hydrogen or C1-6 alkyl are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1Dα receptor subtype relative to the 5-HT1Dβ subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists. STR1

Azetidine, pyrrolidine and piperidine derivatives

A class of substituted azetidine, pyrrolidine and piperidine derivatives are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1Dα receptor subtype relative to the 5-HT1Dβ subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.