74258-81-4

Basic information

• Product Name: 3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine
• Synonyms: 3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine
• CAS NO: 74258-81-4
• Molecular Weight: 250.257
• Mol File: 74258-81-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine(74258-81-4)
• EPA Substance Registry System: 3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine(74258-81-4)

Safety Data

• Hazardous Substances Data: 74258-81-4(Hazardous Substances Data)

Upstream product

• 83796-54-7 2-(3,4,5-trimethoxyphenyl)hydrazine-1-carboxamide 
• 47001-16-1 C₁₁H₁₆N₄O₄ 
• 3291-03-0 3,4,5-trimethoxybenzohydrazide 
• 118-41-2 Eudesmic acid 
• 10308-82-4 aminoguanidine nitrate 

Downstream Products

• 74258-54-1 6-(2-hydroxyethyl)-5-methyl-2-(3,4,5-trimethoxyphenyl)-1,2,4-triazolo<1,5-a>pyrimidin-7(4H)-one 

Relevant articles and documents

Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold

Based on our previous research, thirty new 5-amino-1H-1,2,4-triazoles possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities. Among them, compounds IIa, IIIh, and IIIm demonstrated significant antiproliferative activities against a panel of tumor cell lines, and the promising compound IIIm dose-dependently caused G2/M phase arrest in HeLa cells. Furthermore, analogue IIa exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 9.4 μM, and molecular modeling studies revealed that IIa formed stable interactions in the colchicine-binding site of tubulin, suggesting that 5-amino-1H-1,2,4-triazole scaffold has potential for further investigation to develop novel tubulin polymerization inhibitors with anticancer activity.

Synthesis, anticancer activity and molecular modeling studies of 1,2,4-triazole derivatives as EGFR inhibitors

A series of novel compounds carrying 1,2,4-triazole scaffold were prepared and evaluated for their antiproliferative activities against NCI 60 cell line. Compounds 10 (a, c), 11 (a-d), and 14 (a-e) were selected for evaluation at single concentration of 10 μM towards panel of sixty cancer cell lines. Some of nitric oxide (NO) donating triazole/oxime hybrids 11a-d showed antiproliferative activity better than their corresponding ketones. On the other hand, the thiazolo [3,2-b][1,2,4]-triazoles 14a-e showed remarkable antiproliferative activities against the same cell lines. Compound 14d was selected for five dose testing against the full panel of 60 human tumor cell lines. Compound 14d showed high selectivity against renal subpanel with selectivity ratio of 6.99 at GI50 level. Compounds 11a-d, 10a-d and 14a-e were tested against four cell lines using MTT assay then compounds of the least IC50 were evaluated against three known anticancer targets including EGFR, BRAF and Tubulin. The results revealed that compound 14d showed promising EGFR inhibitory activity of cancer cell proliferation and were also observed to be moderate BRAF and tubulin inhibitors. Moreover, cell cycle analysis and apoptosis assay were finished for compounds 14d and 14f. Finally molecular modeling studies were performed to explore the binding mode of the most active compounds to the target enzymes.