Year-end Sale % OFF 
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.
Highlights
Bisphosphonic acids constitute a class of compounds that exhibit a wide variety of biological activities
3-Amino-1,2,4-triazole is an interesting substrate for the reaction with triethyl orthoformate and diethyl phosphite phosphite because becauseititpossesses possessesmultiple multiplegroups groups that can serve amino component in that can serve as as thethe amino component in the the reaction—namely, amino moiety side-chainand andthe thetriazole triazoleamine
Analysis of the crude mixture, mixture, obtained after hydrolysis, indicated the formation of the expected mono-substituted obtained after hydrolysis, indicated the formation of the expected mono-substituted 1,2,4-triazolyl1,2,4-triazolyl-3-yl-aminomethylenebisphosphonic acid as the major a
Summary
Bisphosphonic acids constitute a class of compounds that exhibit a wide variety of biological activities. Because the three-component reaction usually yields a complex mixture chloroiminium salts [11,12,13,14]. Because the three-component reaction usually yields a complex mixture of products productsthat thatare are difficult to separate, the resulting not isolated. Instead,Instead, the crude reaction reaction mixture is hydrolysed, yielding the bisphosphonic acid, which is subsequently isolated. Mixture is hydrolysed, yielding the bisphosphonic acid, which is subsequently isolated. Because characterize the pharmacological properties of bisphosphonates in vitro are performed in osteoclast characterize the pharmacological properties of bisphosphonates in vitro are performed in osteoclast surrogates, e.g., e.g., macrophages macrophages with with J774E These macrophages macrophages and and osteoclasts osteoclasts are are both both derived derived from from surrogates, the haematopoietic bone particles [15]. The haematopoietic lineage lineageand andare arehighly highlyendocytic endocyticand andcapable capableofofdemineralizing demineralizing bone particles
Sign-in/Register to view highlights & summary 
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
