3929-18-8Relevant articles and documents
Inhibition of Copper Corrosion with N-Arylaminotriazoles in Aqueous Chloride Solutions and in Air
Kipriyanova, G. O.,Komarova, E. S.,Kozaderov, O. A.,Kruzhilin, A. A.,Potapov, A. Yu.,Prabhakar, Ch.,Shevtsov, D. S.,Shikhaliev, Kh. S.,Tripathi, A.,Zartsyn, I. D.
, p. 1152 - 1159 (2020/10/02)
Abstract: A series of 3-(N-arylamino)-5-amino-1Н-1,2,4-triazoles were prepared by the reaction of S,S-dimethyl cyanodithioimidocarbamate with appropriate anilines. The inhibiting effect of the products on the corrosion of copper of M1 grade in acidic and neutral chloride-containing media was studied using electrochemical and accelerated electroless methods. The maximal degree of protection ensured by commercially available 3,5-diamino-1H-1,2,4-triazole and the synthesized 3-phenylamino, 3-(4-methylphenylamino), 3-(4-chlorophenylamino), and 3-(3-chlorophenylamino) derivatives of 5-amino-1Н-1,2,4-triazole reaches 70–87%. In acid solutions, the synthesized compounds show higher performance than the 3,5-diamino derivative, ensuring up to 92–96% protection. Similar results were obtained in experiments in a salt fog chamber.
A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines
Kalinina, Svetlana A.,Kalinin, Dmitrii V.,Dolzhenko, Anton V.
, p. 5537 - 5540 (2013/09/23)
A new, efficient, catalyst-free, one-pot, three-component method for the synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines using 3,5-diamino-1,2,4-triazoles, cyanamide, and triethyl orthoformate is developed. The reaction proceeds smoothly under microwave-assisted heating. Advantages of the method include using easily available reagents, short reaction times, and operational simplicity.
Highly potent inhibitors of methionine aminopeptidase-2 based on a 1,2,4-triazole pharmacophore
Marino Jr., Joseph P.,Fisher, Paul W.,Hofmann, Glenn A.,Kirkpatrick, Robert B.,Janson, Cheryl A.,Johnson, Randall K.,Ma, Chun,Mattern, Michael,Meek, Thomas D.,Ryan, M. Dominic,Schulz, Christina,Smith, Ward W.,Tew, David G.,Tomazek Jr., Thaddeus A.,Veber, Daniel F.,Xiong, Wenfang C.,Yamamoto, Yuuichi,Yamashita, Keizo,Yang, Guang,Thompson, Scott K.
, p. 3777 - 3785 (2008/02/11)
High-throughput screening for inhibitors of the human metalloprotease, methionine aminopeptidase-2 (MetAP2), identified a potent class of 3-anilino-5-benzylthio-1,2,4-triazole compounds. Efficient array and interative synthesis of triazoles led to rapid SAR development around the aniline, benzylthio, and triazole moeities. Evaluation of these analogs in a human MetAP2 enzyme assay led to the identification of several inhibitors with potencies in the 50-100 picomolar range. The deleterious effects on inhibitor potency by methylation of the anilino-triazole nitrogens, as well as the X-ray crystal structure of triazole 102 bound in the active site of MetAP2, confirm the key interactions between the triazole nitrogens, the active site cobalt atoms, and the His-231 side-chain. The structure has also provided a rationale for interpreting SAR within the triazole series. Key aniline (2-isopropylphenyl) and sulfur substituents (furanylmethyl) identified in the SAR studies led to the identification of potent inhibitors (103 and 104) of endothelial cell proliferation. Triazoles 103 and 104 also exhibited dose-dependent activity in an aortic ring tissue model of angiogenesis highlighting the potential utility of MetAP2 inhibitors as anticancer agents.
