Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products
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 posse...
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| Format: | Article |
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MDPI AG
2017-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/22/2/254 |
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| author | Patrycja Miszczyk Dorota Wieczorek Joanna Gałęzowska Błażej Dziuk Joanna Wietrzyk Ewa Chmielewska |
| author_facet | Patrycja Miszczyk Dorota Wieczorek Joanna Gałęzowska Błażej Dziuk Joanna Wietrzyk Ewa Chmielewska |
| author_sort | Patrycja Miszczyk |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-21T16:35:24Z |
| format | Article |
| id | doaj.art-3b1f047d6e8644148da2afb21dffcde8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T16:35:24Z |
| publishDate | 2017-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3b1f047d6e8644148da2afb21dffcde82022-12-21T18:57:15ZengMDPI AGMolecules1420-30492017-02-0122225410.3390/molecules22020254molecules22020254Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the ProductsPatrycja Miszczyk0Dorota Wieczorek1Joanna Gałęzowska2Błażej Dziuk3Joanna Wietrzyk4Ewa Chmielewska5Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, 50-370 Wrocław, PolandFaculty of Chemistry, University of Opole, 45-040 Opole, PolandDepartment of Inorganic Chemistry, Faculty of Pharmacy, Wrocław Medical University, 50-556 Wrocław, PolandFaculty of Chemistry, University of Opole, 45-040 Opole, PolandLudwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 53-114 Wrocław, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, 50-370 Wrocław, PolandThe 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.http://www.mdpi.com/1420-3049/22/2/254organophosphorus chemistrybisphosphonic acidsaminomethylenebisphosponatesthree-component reactiontriazoleP-containing drugsanti-proliferative activityosteoclastsUV-Vis spectroscopypH-titrationpotentiometrycrystallography |
| spellingShingle | Patrycja Miszczyk Dorota Wieczorek Joanna Gałęzowska Błażej Dziuk Joanna Wietrzyk Ewa Chmielewska Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products Molecules organophosphorus chemistry bisphosphonic acids aminomethylenebisphosponates three-component reaction triazole P-containing drugs anti-proliferative activity osteoclasts UV-Vis spectroscopy pH-titration potentiometry crystallography |
| title | Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products |
| title_full | Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products |
| title_fullStr | Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products |
| title_full_unstemmed | Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products |
| title_short | Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities of the Products |
| title_sort | reaction of 3 amino 1 2 4 triazole with diethyl phosphite and triethyl orthoformate acid base properties and antiosteoporotic activities of the products |
| topic | organophosphorus chemistry bisphosphonic acids aminomethylenebisphosponates three-component reaction triazole P-containing drugs anti-proliferative activity osteoclasts UV-Vis spectroscopy pH-titration potentiometry crystallography |
| url | http://www.mdpi.com/1420-3049/22/2/254 |
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