289710-96-9

Usage

Uses

Used in Pharmaceutical Industry:
5-(3-Methoxyphenyl)-4H-1,2,4-triazol-3-amine is utilized as a pharmaceutical agent for its antifungal, antibacterial, and antitumor properties. Its diverse biological activities make it a promising candidate for the development of new medications targeting a range of health conditions.
Used in Agricultural Applications:
In agriculture, 5-(3-Methoxyphenyl)-4H-1,2,4-triazol-3-amine is employed as a bioactive compound to combat fungal and bacterial infections in crops. Its application helps in enhancing crop yield and quality by protecting plants from diseases.
The unique chemical structure of 5-(3-Methoxyphenyl)-4H-1,2,4-triazol-3-amine, coupled with its wide-ranging potential applications, positions it as a significant subject of research for scientists in chemistry, medicine, and agriculture, who are continually exploring its capabilities and optimizing its use for the betterment of human health and agricultural practices.

InChI:InChI=1/C9H10N4O/c1-14-7-4-2-3-6(5-7)8-11-9(10)13-12-8/h2-5H,1H3,(H3,10,11,12,13)

Upstream product

• 5785-06-8 3-methoxybenzoic hydrazide 
• 17356-08-0 thiourea 
• 1711-05-3 m-anisoyl chloride 

Downstream Products

• 1456613-79-8 2-(3-methoxyphenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one 
• 1456614-07-5 C₁₃H₁₅N₅O₃S 
• 1465270-02-3 7-amino-2-(3-methoxyphenyl)-1,2,4-triazolo[1,5-a][1,3,5]triazine 
• 1410904-78-7 2-(3-methoxyphenyl)-5-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazine 
• 1410904-66-3 N-[3⁽⁵⁾-(3-methoxyphenyl)-1,2,4-triazol-5⁽³⁾-yl]trichloroacetamidine 

Relevant academic research and scientific papers

A green one-pot synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines as potential antimicrobial agents

Abstract: An efficient procedure was proposed for the synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines via a one-pot reaction of thiourea, dimethyl sulfate and various hydrazides. 1,2,4-Triazole derivatives were prepared in aqueous media under mild conditions while adhering to some principles of green chemistry. The products were easily isolated in 83–95% yields without any need for further purification. Inhibitory activities of all synthetic compounds were assessed against a variety of Gram-positive and Gram-negative pathogenic bacteria as well as some fungal pathogens. The best antibacterial effects were observed with 3(5)-phenyl-1H-1,2,4-triazol-5(3)-amine according to its MIC values (4–8?μg?mL?1). All compounds were successful in blocking the growth of fungi. Acceptable antioxidant properties were observed only with 3(5)-(4-nitrophenyl)-1H-1,2,4-triazol-5(3)-amine. Graphic abstract: 3(5)-Substituted 1,2,4-triazol-5(3)-amines were efficiently prepared via a one-pot reaction of thiourea, dimethyl sulfate and various hydrazides in water as the solvent. Inhibitory activity of all synthesized derivatives was proved according to their MIC, MBC and MFC values. It is found that they are potential antifungal agents.[Figure not available: see fulltext.].

3-Aryl/Heteroaryl-5-amino-1-(3′,4′,5′-trimethoxybenzoyl)-1,2,4-triazoles as antimicrotubule agents. Design, synthesis, antiproliferative activity and inhibition of tubulin polymerization

Many natural and synthetic substances are known to interfere with the dynamic assembly of tubulin, preventing the formation of microtubules. In our search for potent and selective antitumor agents, a novel series of 1-(3′,4′,5′-trimethoxybenzoyl)-5-amino-1,2,4-triazoles were synthesized. The compounds had different heterocycles, including thiophene, furan or the three isomeric pyridines, and they possessed a phenyl ring bearing electron-releasing or electron-withdrawing substituents at the 3-position of the 5-amino-1,2,4-triazole system. Most of the twenty-two tested compounds showed moderate to potent antiproliferative activities against a panel of solid tumor and leukemic cell lines, with four (5j, 5k, 5o and 5p) showing strong antiproliferative activity (IC50 50 values 2-100-fold lower for Jurkat and RS4;11 cells than those for the three lines derived from solid tumors (HeLa, HT-29 and MCF-7 cells). Compound 5k strongly inhibited tubulin assembly, with an IC50 value of 0.66 μM, half that obtained in simultaneous experiments with CA-4 (IC50 = 1.3 μM).

A structure-activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5] triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities

Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. Th