36209-49-1

Usage

Uses

Used in Pharmaceutical Industry:
AMPT is used as a potential anticancer agent for its ability to inhibit thymidylate synthase, an enzyme essential for DNA synthesis and repair. By suppressing the activity of this enzyme, AMPT can lead to the suppression of tumor cell growth, making it a candidate for the development of cancer therapeutics.
AMPT is also used as an inducer of apoptosis, or programmed cell death, in cancer cells. This property further supports its potential as a therapeutic agent in the treatment of various types of cancer.
While the provided materials do not specify different applications in various industries, the primary focus of AMPT's use is within the pharmaceutical industry for its potential as a cancer treatment. If future research uncovers additional applications in other industries, they can be listed separately following the same format.

InChI:InChI=1/C9H10N4OS/c1-14-7-4-2-6(3-5-7)8-11-12-9(15)13(8)10/h2-5H,10H2,1H3,(H,12,15)

Upstream product

• 121-98-2 methyl 4-methoxybenzoate 
• 2231-57-4 Thiocarbohydrazide 
• 75-15-0 carbon disulfide 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 94-30-4 ethyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 451-82-1 (2-fluorophenyl)acetic acid 
• 85103-41-9 potassium N-(4-methoxybenzoyl)hydrazinecarbodithioate 
• 10364-93-9 1-(4-methoxybenzoyl)-imidazole 
• 83511-12-0 acetic p-anisic anhydride 
• 23766-26-9 5?(4?methoxyphenyl)?1,3,4?oxadiazole?2?thiol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 116622-94-7 2-(2-fluorophenyl)acetohydrazide 
• 57486-67-6 methyl o-fluorophenylacetate 

Downstream Products

• 113486-93-4 6,6'-Bis<3-(4-methoxyphenyl)-s-triazolo<3,4-b><1,3,4>thiadiazole> 
• 85106-42-9 7H-3-(4-Methoxyphenyl)-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine 
• 1202208-33-0 C₁₈H₁₉N₅OS 
• 1293362-44-3 methyl 3-(3-(4-methoxyphenyl)-5-thioxo-1H-1,2,4-triazol-4-ylimino)cholanate 
• 1400796-58-8 methyl 3α-(2-(4-amino-3-(4-methoxyphenyl)-5-thioxo-4,5-dihydro-1,2,4-triazol-1-yl)acetoxy)-12α-hydroxycholanate 
• 1427501-07-2 6-(furan-3-yl)-3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 849913-13-9 3-(4-methoxyphenyl)-6-(pyridin-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 537017-29-1 3-(4-methoxyphenyl)-6-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 577700-42-6 3-(4-methoxyphenyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 578754-51-5 3-(4-ethoxyphenyl)-6-(thiophen-2-ylmethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 13228-89-2 3-p-methoxyphenyl-6-mercapto-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole 
• 120450-04-6 2-(4-Methoxy-phenyl)-9-thia-1,3,3a,8-tetraaza-cyclopenta[b]naphthalen-4-one 
• 117376-46-2 3-(4-Methoxy-phenyl)-4H-11-thia-1,2,3a,4,5,10-hexaaza-cyclopenta[b]anthracene 

Relevant academic research and scientific papers

An extensive research on aldose reductase inhibitory effects of new 4H-1,2,4-triazole derivatives

Aldose reductase (AR) is a key enzyme, which triggers the excessive accumulation of sorbitol in insulin independent tissues leading to severe diabetes-induced microvascular complications. Substantial evidence has proven that AR inhibition is a well-establ

Efficient Synthesis of Fluorinated [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazoles

Abstract: An efficient synthesis of fluorinated [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives has been achievedby cyclocondensation of 5-substituted 4-amino-1,2,4-triazole-3-thiols withfluoro-substituted aromatic acids using phosphoryl chloride as a cyclizingagent. The synthesized compounds were characterized by spectroscopic techniques,including IR, 1H NMR, and mass spectra.

Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification

In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. A series of novel triazolyl pyrazole derivatives (10a-y) in which thiol bearing triazole moiety as the zinc binding functional group was introduced to a pyrazole based pharmacophore was synthesized and evaluated as potent and selective inhibitors of h-TNAP over h-NPP1. The biological screening against h-TNAP, h-IAP, h-NPP1 and h-NPP3 showed that many of the synthesized compounds are selective inhibitors of TNAP. Particularly, the compounds 10a-h, 10j, 10m-q, 10u, 10w and 10x displayed high potency and complete selectivity towards h-TNAP over h-NPP1. Compound 10q emerged as a highly potent inhibitor (IC50 = 0.16 μM or 160 nM) against h-TNAP with 127-fold increased inhibition compared to levamisole. On the other hand, compound 10e was found to be most selective inhibitor against the tested APs and NPPs (IC50 = 1.59 ± 0.36 μM). Binding sites architecture analysis, molecular-docking and molecular dynamics simulations (MDS), revealed the basis for h-TNAP and h-IAP ligand selectivity as well as selectivity towards h-TNAP over h-NPP1. These newly discovered inhibitors are believed to represent valuable lead structures to further streamline the generation of candidate compounds to target VC.

Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.

Synthesis and antimicrobial activity of piperine analogues containing 1,2,4-triazole ring

A series 1,2,4-triazole piperine analogues (TP1-TP6) were designed and synthesized. The structures were confirmed using 1H NMR and 13C NMR. Antibacterial study was done using Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative microorganisms (E. coli and Pseudomonas aeruginosa) by disc diffusion method. Compound containing chloro substitution (TP6) showed the highest effect, while compound TP1, TP3, TP4, TP5 showed the moderate activity.

Synthesis and antitumor evaluation of novel fused heterocyclic 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives

In this study, twenty three 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives were synthesized and their antiproliferative activities in vitro were studied against SMMC-7721, HeLa, A549, and L929 by the CCK-8 assay. The bioassay results demonstrated that all tested compounds 8(a–w) exhibited antiproliferation with different degrees, and some compounds showed better effects than reference drug 5-fluorouracil. Among these screened compounds, compounds 8a, 8d, and 8l displayed significant antitumor activities in inhibiting SMMC-7721cell proliferation with IC50 values of 1.64, 1.74, and 1.61 μM, respectively. Compounds 8d and 8l were manifested highly effective biological activity versus HeLa cells with IC50 values of 2.23 and 2.84 μM, respectively. Compound 8l was found to have the highest antitumor potency against A549 cells with IC50 value of 2.67 μM. Furthermore, all compounds exhibited weaker cytotoxic effects than 5-fluorouracil on normal cell lines L929.

Symmetrical heterocyclic cage skeleton: Synthesis, urease inhibition activity, kinetic mechanistic insight, and molecular docking analyses

The present study focuses on the design and synthesis of a cage-like organic skeleton containing two triazole rings jointed via imine linkage. These molecules can act as urease inhibitors. The in-vitro urease inhibition screening results showed that the combination of the two triazole skeleton in the cage-like morphology exhibited comparable urease inhibition activity to that of the reference thiourea while the metallic complexation, especially with copper, nickel, and palladium, showed excellent activity results with IC50 values of 0.94 ± 0.13, 3.71 ± 0.61, and 7.64 ± 1.21 (3a–c), and 1.20 ± 0.52, 3.93 ± 0.45, and 12.87 ± 2.11 μM (4a–c). However, the rest of compounds among the targeted series exhibited a low to moderate enzyme inhibition potential. To better understand the compounds’ underlying mechanisms of the inhibitory effect (3a and 4a) and their most active metal complexes (3b and 4b), we performed an enzymatic kinetic analysis using the Lineweaver–Burk plot in the presence of different concentrations of inhibitors to represent the non-competitive inhibition nature of the compounds, 3a, 4a, and 4b, while mixed type inhibition was represented by the compound, 3b. Moreover, molecular docking confirmed the binding interactive behavior of 3a within the active site of the target protein.

Investigation on 4-amino-5-substituent-1,2,4-triazole-3-thione Schiff bases an antifungal drug by characterization (spectroscopic, XRD), biological activities, molecular docking studies and electrostatic potential (ESP)

Four novel Schiff bases 4-(2,4-dinitrobenzylideneamino)-5-m-tolyl-2H-1,2,4-triazole-3(4H)-thione) (F1), 4-(2,4-dinitrobenzylideneamino)-5-(2-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione) (F2), 4-(2,4-dinitrobenzylideneamino)-5-(3-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione) (F3) and 4-(2,4-dinitrobenzylideneamino)-5-(4-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione) (F4) were prepared as new antifungal compounds contributing 4-Amino-5-Substituent-1,2,4-Triazole-3-Thione and 2,4-dinitrobenzaldehyde via a condensation reaction under the mild conditions with excellent yields. The structures of compounds were characterized by elemental analysis (EA), FT-IR, 1H NMR, 13C NMR spectra and X-ray analysis. In addition, the compounds were screened for in vitro biological activity, and the bioassay results indicated that the newly synthesized compounds showed different in vitro antifungal activities against five plant fungi. Particularly, compound F3 (EC50 = 11.16 mg/L) was found to be the most active respectively against Wheat gibberellic, even more effective than Fluconazole (EC50 = 16.03 mg/L). The active compounds were further evaluated for enzyme inhibition efficacy against the receptor CYP51 by docking. Meanwhile, an explicit surface analysis on compounds were carried out theoretically using the wave function analyzer (Multiwfn 3.4.1 software) in order to study the reactivity of the compounds.

Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles Against MDR Strain of Mycobacterium tuberculosis

Emergence of various forms of resistant strains of Mycobacterium tuberculosis led to the exploration of drugs with novel mechanism of action. Recently econazole, an azole based antitubercular agent, attracted major attention for targeting mycobacterial cytochrome P450. In the present study, we designed novel 1,2,4-triazole derivatives based on econazole moiety and evaluated them for in vitro antitubercular activity against M. tuberculosis H37Rv and multi-drug resistant (MDR) strains of Mycobacterium.

Design, Synthesis, and Antifungal Activities of Novel 1,2,4-Triazole Schiff Base Derivatives

With the aim to find new compounds with high antifungal activity, 21 4-amino-5-substituted-1,2,4-triazole Schiff bases (2a?–?2g, 3a?–?3g, and 4a?–?4g) were designed and synthesized. Their antifungal activities against Pythium solani, Gibberlla nicotiancola, Fusarium oxysporium f. sp. niveum, Gibberlla saubinetii, Alternaria iycopersici, Phytophthora capsici, Physalospora piricola, Cercospora arachidicola hori, and Fusarium oxysporium f. sp. cucumber were tested, parts of the compounds exhibited excellent antifungal activity. This research provides useful information for further study of antifungal agents.