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Molecules 2017, 22(2), 254; doi:10.3390/molecules22020254

Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products

1
Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, 50-370 Wrocław, Poland
2
Faculty of Chemistry, University of Opole, 45-040 Opole, Poland
3
Department of Inorganic Chemistry, Faculty of Pharmacy, Wrocław Medical University, 50-556 Wrocław, Poland
4
Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 53-114 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Academic Editors: Diego Muñoz-Torrero, Rodolfo Lavilla and Christopher Hulme
Received: 3 January 2017 / Revised: 30 January 2017 / Accepted: 3 February 2017 / Published: 8 February 2017
(This article belongs to the Special Issue Multicomponent Reaction-Based Synthesis of Bioactive Molecules)
View Full-Text   |   Download PDF [2134 KB, uploaded 9 February 2017]   |  

Abstract

The reaction of diethyl phosphite with triethyl orthoformate and a primary amine followed by hydrolysis is presented, and the reaction was suitable for the preparation of (aminomethylene)bisphosphonates. 3-Amino-1,2,4-triazole was chosen as an interesting substrate for this reaction because it possesses multiple groups that can serve as the amino component in the reaction—namely, the side-chain and triazole amines. This substrate readily forms 1,2,4-triazolyl-3-yl-aminomethylenebisphosphonic acid (compound 1) as a major product, along with N-ethylated bisphosphonates as side products. The in vitro antiproliferative effects of the synthesized aminomethylenebisphosphonic acids against J774E macrophages were determined. These compounds exhibit similar activity to zoledronic acid and higher activity than incadronic acid. View Full-Text
Keywords: organophosphorus chemistry; bisphosphonic acids; aminomethylenebisphosponates; three-component reaction; triazole; P-containing drugs; anti-proliferative activity; osteoclasts; UV-Vis spectroscopy; pH-titration; potentiometry; crystallography organophosphorus chemistry; bisphosphonic acids; aminomethylenebisphosponates; three-component reaction; triazole; P-containing drugs; anti-proliferative activity; osteoclasts; UV-Vis spectroscopy; pH-titration; potentiometry; crystallography
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Miszczyk, P.; Wieczorek, D.; Gałęzowska, J.; Dziuk, B.; Wietrzyk, J.; Chmielewska, E. Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products. Molecules 2017, 22, 254.

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