154594-15-7

Basic information

• Product Name: 4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE
• Synonyms: 4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE;4-(4-Acetamidophenyl)-1,2,4-triazole;N-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetaMide
• CAS NO: 154594-15-7
• Molecular Formula: C₁₀H₁₀N₄O
• Molecular Weight: 202.21
• Mol File: 154594-15-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 284-286°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.28g/cm³
• Refractive Index: 1.646
• BRN: 7639486
• CAS DataBase Reference: 4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE(154594-15-7)
• EPA Substance Registry System: 4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE(154594-15-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 154594-15-7(Hazardous Substances Data)

Usage

Description

4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE is a chemical compound with the molecular formula C11H11N5O. It is an acetanilide derivative with a triazole ring attached to the amine group of the acetanilide. 4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE is often used in medicinal and pharmaceutical research as a building block for the synthesis of various pharmaceuticals and biologically active molecules.

Uses

Used in Pharmaceutical Research:
4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE is used as a building block for the synthesis of various pharmaceuticals and biologically active molecules. Its unique structure allows for the development of new drugs with potential applications in treating various diseases and conditions.
Used in Medicinal Chemistry:
4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE is used as a key intermediate in the synthesis of pharmacologically active compounds. Its presence in these compounds can contribute to their therapeutic effects and help in the development of new medications.
Used in Anticancer Research:
4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE has been studied for its potential use in the treatment of various cancers. Its unique chemical structure may allow it to target specific cancer cells and inhibit their growth, making it a promising candidate for further research and development in oncology.
Used in Antimicrobial and Antifungal Applications:
4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE has been investigated for its antimicrobial and antifungal properties. Its ability to inhibit the growth of certain microorganisms makes it a potential candidate for use in the development of new antibiotics and antifungal agents to combat drug-resistant infections.
Used in the Medical and Pharmaceutical Industries:
4-(1,2,4-TRIAZOL-4-YL)ACETANILIDE is an important intermediate in the synthesis of various pharmacologically active compounds and has potential applications in the medical and pharmaceutical industries. Its versatility and unique structure make it a valuable asset in the development of new drugs and therapies.

InChI:InChI=1/C10H10N4O/c1-8(15)13-9-2-4-10(5-3-9)14-6-11-12-7-14/h2-7H,1H3,(H,13,15)

Upstream product

• 624-84-0 formic acid hydrazide 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 16114-05-9 N,N'-bis(dimethylaminomethylene)hydrazine 
• 16227-06-8 N,N-dimethylformamide azine dihydrochloride 

Downstream Products

• 1266335-98-1 N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide 
• 177947-69-2 2-iodo-4-(1,2,4-triazol-4-yl)aniline 
• 177945-75-4 (3S)-3-(N-benzyl)aminomethyl-1-[2-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)ethyl]pyrrolidine 

Relevant articles and documents

Synthesis of ring-opened derivatives of triazole-containing quinolinones and their antidepressant and anticonvulsant activities

Based on the potent antidepressant and anticonvulsant activities of the triazole-containing quinolinones reported in our previous work, a series of ring-opened derivatives of them were designed, synthesized in this work. Their antidepressant and anticonvulsant activities were screened using the forced swimming test (FST) and the maximal electroshock seizure test (MES), respectively. The results showed that compounds 4a, 5a, 6c-6e, 6g-6i, and 7 led to significant reductions in the accumulated immobility time in the FST at a dose of 50 mg/kg. Especially compound 7 exhibited higher levels of efficacy than the reference standard fluoxetine in the FST and the tail suspension test. The results of an open field test excluded the possibility of central nervous stimulation of 7, which further confirmed its antidepressant effect. Meanwhile, compounds 6a-6i and 7 showed different degrees of anticonvulsant activity in mice at the doses range from 300 to 30 mg/kg in the MES. Among them, compounds 6e and 7 displayed the ED50 of 38.5 and 32.7 mg/kg in the MES, and TD50 of 254.6 and 245.5 mg/kg, respectively. No one showed neurotoxicity at the dose of 100 mg/kg. The preliminary investigation forward to their mechanism indicated that regulation of GABAergic system might contribute to their anticonvulsive and anti-depressive action.

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.