23159-61-7Relevant academic research and scientific papers
Synthesis of α-substituted 2-(1H-1,2,4-triazol-3-yl)acetates and 5-amino-2,4-dihydro-3H-pyrazol-3-ones via the Pinner strategy
Khomenko, Dmytro M.,Doroshchuk, Roman O.,Ivanova, Hanna V.,Zakharchenko, Borys V.,Raspertova, Ilona V.,Vaschenko, Oleksandr V.,Shova, Sergiu,Dobrydnev, Alexey V.,Moroz, Yurii S.,Grygorenko, Oleksandr O.,Lampeka, Rostyslav D.
, (2021/03/17)
A series of 2-(1H-1,2,4-triazol-3-yl)acetates, as well as 4-mono- and 4,4-disubstituted 5-amino-2,4-dihydro-3H-pyrazol-3-ones (including spirocyclic derivatives) have been synthesized using the Pinner reaction strategy. α-Mono- and α,α-disubstituted ethyl cyanoacetates were converted into the corresponding carboxyimidate salts that served as the key intermediates. Their further reaction with formylhydrazide or hydrazine hydrate provided triazolylacetates or aminopyrazolones (including spirocyclic derivatives), depending on the structure of the starting Pinner salt and the nature of the nucleophile. The scope and limitations of the developed synthetic method have been established.
Discovery of novel, highly potent, and selective matrix metalloproteinase (MMP)-13 inhibitors with a 1,2,4-triazol-3-yl moiety as a zinc binding group using a structure-based design approach
Nara, Hiroshi,Kaieda, Akira,Sato, Kenjiro,Naito, Takako,Mototani, Hideyuki,Oki, Hideyuki,Yamamoto, Yoshio,Kuno, Haruhiko,Santou, Takashi,Kanzaki, Naoyuki,Terauchi, Jun,Uchikawa, Osamu,Kori, Masakuni
, p. 608 - 626 (2017/02/05)
On the basis of a superposition study of X-ray crystal structures of complexes of quinazoline derivative 1 and triazole derivative 2 with matrix metalloproteinase (MMP)-13 catalytic domain, a novel series of fused pyrimidine compounds which possess a 1,2,4-triazol-3-yl group as a zinc binding group (ZBG) was designed. Among the herein described and evaluated compounds, 31f exhibited excellent potency for MMP-13 (IC50 = 0.036 nM) and selectivities (greater than 1,500-fold) over other MMPs (MMP-1, -2, -3, -7, -8, -9, -10, and -14) and tumor necrosis factor-α converting enzyme (TACE). Furthermore, the inhibitor was shown to protect bovine nasal cartilage explants against degradation induced by interleukin-1 and oncostatin M. In this article, we report the discovery of extremely potent, highly selective, and orally bioavailable fused pyrimidine derivatives that possess a 1,2,4-triazol-3-yl group as a novel ZBG for selective MMP-13 inhibition.
Design and chemical synthesis of [1,2,4]triazol[1,5-c]pyrimidin-5-yl amines, a novel class of VEGFR-2 kinase inhibitors
Kiselyov, Alexander S.,Piatnitski Chekler, Eugene L.,Chernisheva, Natalia B.,Salamandra, Lev K.,Semenov, Victor V.
supporting information; experimental part, p. 3809 - 3812 (2009/10/11)
The Letter describes a facile approach to 7,8-dihydro[1,2,4]triazol[1,5-c]pyrimidin-5-yl amines, a novel class of potent inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). The synthetic sequence is centered around preparation of the k
HETEROCYCLIC AMIDE COMPOUND AND USE THEREOF
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Page/Page column 111, (2008/12/07)
The present invention provides a novel amide compound represented by the following formula, which has a matrix metalloproteinase inhibitory activity and is useful as a pharmaceutical agent. wherein each symbol is as defined in the specification.
