59301-21-2

Usage

Uses

Used in Organic Synthesis:
5-(4-Nitrophenyl)-4H-1,2,4-triazol-3-amine is used as a building block in organic synthesis for the creation of complex organic molecules. Its reactivity and structural features make it a valuable component in the synthesis of pharmaceuticals and other organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-(4-Nitrophenyl)-4H-1,2,4-triazol-3-amine is used as a research compound for exploring its potential biological activities. It has been studied for its possible anti-inflammatory and antimicrobial properties, which could lead to the development of new therapeutic agents.
Used in Drug Development:
5-(4-Nitrophenyl)-4H-1,2,4-triazol-3-amine is utilized in the development of new drugs due to its potential applications in medicinal chemistry. Its unique structure allows for the design of novel drug candidates that could address various health conditions.
Used in Agrochemicals:
In the agrochemical sector, 5-(4-Nitrophenyl)-4H-1,2,4-triazol-3-amine is used as a starting material or intermediate in the synthesis of new agrochemicals. Its potential biological activities may contribute to the development of effective pesticides or other agricultural products.
Used in Organic Chemistry Research:
5-(4-Nitrophenyl)-4H-1,2,4-triazol-3-amine serves as a valuable tool in the study of organic chemistry, particularly in understanding the reactivity and properties of triazole derivatives. Its unique structure aids researchers in exploring new reaction pathways and mechanisms.

InChI:InChI=1/C8H7N5O2/c9-8-10-7(11-12-8)5-1-3-6(4-2-5)13(14)15/h1-4H,(H3,9,10,11,12)

Upstream product

• 3679-93-4 4-Nitrobenzoic acid 2-amidinohydrazide 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 122-04-3 4-nitro-benzoyl chloride 
• 3679-93-4 C₈H₉N₅O₃ 
• 17356-08-0 thiourea 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 555-16-8 4-nitrobenzaldehdye 
• 420-04-2 CYANAMID 
• 1747-50-8 4-methyl-N'-[(4-nitrophenyl)methylidene]benzene-1-sulfonohydrazide 

Downstream Products

• 168893-40-1 5-(4-Amino-phenyl)-2H-[1,2,4]triazol-3-ylamine 
• 26621-63-6 3-nitro-5-(4-nitro-phenyl)-1H-[1,2,4]triazole 
• 106087-55-2 2-(4-Nitrophenyl)-6-nitro-7-oxo-4,7-dihydro<1,5-a>pyrimidine sodium salt 
• 1252014-25-7 C₁₂H₁₂N₆O₄S 
• 20085-46-5 2-(4-nitrophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one 

Relevant academic research and scientific papers

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

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

Synthesis of Nitrogen-containing Heterocycles under Conditions of Microwave Heating

The efficiency of microwave heating for performing fast organic reactions is demonstrated with synthesis of nitrogen-containing heterocycles and intermediates as an example.

Triazole derivative and pharmaceutical use thereof

An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) STR1 or the following formula (III) STR2 wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all, have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.

Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia

In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1- [(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the airway through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1- [(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally (ip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD50 value of >2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D4 (LTD4) or platelet-activating factor (PAF)- induced responses. Taken together, these results suggest 23c as a novel candidate for the treatment of chronic asthma. Further studies are now underway.