Killian Oukoloff1, Bobby Lucero2, Karol R Francisco2, Kurt R Brunden3, Carlo Ballatore4. 1. Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA. 2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA. 3. Center for Neurodegenerative Disease Research, Perelman School of Medicine, University of Pennsylvania, 3600 Spruce Street, Philadelphia, PA, 19104-6323, USA. 4. Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA. Electronic address: cballatore@ucsd.edu.
Abstract
The 1,2,4-triazolo[1,5-a]pyrimidine (TP) heterocycle, in spite of its relatively simple structure, has proved to be remarkably versatile as evidenced by its use in many different applications reported over the years in different areas of drug design. For example, as the ring system of TPs is isoelectronic with that of purines, this heterocycle has been proposed as a possible surrogate of the purine ring. However, depending on the choice of substituents, the TP ring has also been described as a potentially viable bio-isostere of the carboxylic acid functional group and of the N-acetyl fragment of ε-N-acetylated lysine. In addition, the metal-chelating properties of the TP ring have also been exploited to generate candidate treatments for cancer and parasitic diseases. In the present review article, we discuss recent applications of the TP scaffold in medicinal chemistry, and provide an overview of its properties and methods of synthesis.
The n class="Chemical">1,2,4-triazolo[1,5-a]pyrimidine (TP) heterocycle, in spite of its relatively simple structure, has proved to be remarkably versatile as evidenced by its use in many different applications reported over the years in different areas of drug design. For example, as the ring system of TPs is isoelectronic with that of n>n class="Chemical">purines, this heterocycle has been proposed as a possible surrogate of the purine ring. However, depending on the choice of substituents, the TP ring has also been described as a potentially viable bio-isostere of the carboxylic acid functional group and of the N-acetyl fragment of ε-N-acetylated lysine. In addition, the metal-chelating properties of the TP ring have also been exploited to generate candidate treatments for cancer and parasitic diseases. In the present review article, we discuss recent applications of the TP scaffold in medicinal chemistry, and provide an overview of its properties and methods of synthesis.
Authors: Warren G Lewis; Luke G Green; Flavio Grynszpan; Zoran Radić; Paul R Carlier; Palmer Taylor; M G Finn; K Barry Sharpless Journal: Angew Chem Int Ed Engl Date: 2002-03-15 Impact factor: 15.336
Authors: Sylvie G Bernier; Nazbeh Taghizadeh; Charles D Thompson; William F Westlin; Gerhard Hannig Journal: J Cell Biochem Date: 2005-08-15 Impact factor: 4.429
Authors: Victor V Fedotov; Vladimir L Rusinov; Evgeny N Ulomsky; Evgeny M Mukhin; Evgeny B Gorbunov; Oleg N Chupakhin Journal: Chem Heterocycl Compd (N Y) Date: 2021-05-15 Impact factor: 1.490
Authors: Daniil N Lyapustin; Svetlana K Kotovskaya; Ilya I Butorin; Evgeny N Ulomsky; Vladimir L Rusinov; Denis A Babkov; Alexander A Pokhlebin; Alexander A Spasov; Vsevolod V Melekhin; Maria D Tokhtueva; Anna V Shcheglova; Oleg G Makeev Journal: Molecules Date: 2022-08-17 Impact factor: 4.927