1-Amino-1,1-bisphosphonates. Fundamental syntheses and new developments

Abstract

1-Amino-1,1-bisphosphonates have become increasingly important in different fields of chemistry, medicine and agriculture. The combination of the unique physical, chemical and biological properties of methylenebisphosphonate and aminophosphonate fragments opens wide possibilities for the design of biologically active compounds including therapeutic agents to treat bone disorders related to calcium metabolism, immunomodulators, anti-infectives and plant growth regulators. The scope of this review is to summarize the existing strategies for the preparation of diversely functionalized 1-amino-1,1-bisphosphonates and to illustrate their utility as synthetic building blocks.

Fully scalable one-pot method for the production of phosphonic graphene derivatives

“…As can be seen, only a few examples of graphene derivatives functionalized with phosphonic acid can be found in the literature. The synthesis of phosphonic and bisphosphonic acids, which are widely used as detergents, pharmaceuticals (mainly for osteoporosis treatment), corrosion inhibitors, selective adsorbents and catalysts, is well known [ 7 – 9 ]. One of the most commonly used reactions is the conversion of carboxylic acids into the respective bisphosphonic acids using a mixture of PCl 3 and H 3 PO 3 [ 9 ].…”

“…The synthesis of phosphonic and bisphosphonic acids, which are widely used as detergents, pharmaceuticals (mainly for osteoporosis treatment), corrosion inhibitors, selective adsorbents and catalysts, is well known [ 7 – 9 ]. One of the most commonly used reactions is the conversion of carboxylic acids into the respective bisphosphonic acids using a mixture of PCl 3 and H 3 PO 3 [ 9 ]. In this paper, we present a reaction adapted from classical organic chemistry as a convenient route for the functionalization of graphene with phosphonate groups.…”

A new method for the synthesis of α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues

“…α-Aminophosphonic and α-aminophosphinic acids, as phosphorus analogues and bioisosters of α-amino acids, exhibit a variety of important biological properties [1–3]. α-Aminobisphosphonates of general formula 1 (Fig.…”

“…α-Aminobisphosphonates of general formula 1 (Fig. 1, X = NHR), that can be considered as one of the most interesting subclass of α-aminophosphonic acids [1,3], are an important class of drugs that are currently successfully being used to treat osteoporosis and similar diseases, including Paget’s disease ( osteitis deformans ), bone metastasis (with or without hypercalcaemia), Kahler’s disease ( multiple myeloma ), primary hyperparathyroidism, brittle bone disease ( osteogenesis imperfecta ), fibrous dysplasia and others [1,4]. α‑Aminobisphosphonates (Fig.…”

“…1, X = NHR) and α‑hydroxybisphosphonates (Fig. 1, X = OH) that can easily be obtained from α‑amino derivatives [5–6] belong to two of the most important subclasses of bisphosphonates with many successful medical applications (Table 1) [1,3–4 7–9]. …”