A Facile Approach for the Synthesis of Α -Halogenated Alkylidenediphosphonates by Reaction of Alkyllithium With Chlorophosphate and Halogen Reagent

Lai, Chunbo; Xi, Chanjuan; Ye, Feng

doi:10.1080/10426500490262621

Cited by 3 publications

(3 citation statements)

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“…This method consists of a reaction between a carboxylic acid and a mixture of phosphorus trichloride or phosphorous acid, followed by hydrolysis under acidic conditions to produce hydroxy-bisphosphonates or their sodium salts (Figure 2). Other methods of synthesis have been described, such as phosphonalkylation [55,56], from bisphosphonate fractions [57,58], by a cross-coupling reaction [59], from aminomethylene-phosphonic acids [60,61], by radical reaction [62,63], from halo substrates [64], and from functional nitrogen substrates [65]. Classical route for the synthesis of hydroxy-bisphosphonates.…”

Section: Chemical and Biological Characteristics Of Bisphosphonate-based Compoundsmentioning

confidence: 99%

Bisphosphonate-Based Molecules as Potential New Antiparasitic Drugs

et al. 2020

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Neglected tropical diseases such as Chagas disease and leishmaniasis affect millions of people around the world. Both diseases affect various parts of the globe and drugs traditionally used in therapy against these diseases have limitations, especially with regard to low efficacy and high toxicity. In this context, the class of bisphosphonate-based compounds has made significant advances regarding the chemical synthesis process as well as the pharmacological properties attributed to these compounds. Among this spectrum of pharmacological activity, bisphosphonate compounds with antiparasitic activity stand out, especially in the treatment of Chagas disease and leishmaniasis caused by Trypanosoma cruzi and Leishmania spp., respectively. Some bisphosphonate compounds can inhibit the mevalonate pathway, an essential metabolic pathway, by interfering with the synthesis of ergosterol, a sterol responsible for the growth and viability of these parasites. Therefore, this review aims to present the information about the importance of these compounds as antiparasitic agents and as potential new drugs to treat Chagas disease and leishmaniasis.

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Section: Chemical and Biological Characteristics Of Bisphosphonate-based Compoundsmentioning

confidence: 99%

Bisphosphonate-Based Molecules as Potential New Antiparasitic Drugs

et al. 2020

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“…Treatment of 48 with NaOBr provided triethyl dibromophosphonoacetate (49) in good yield, and the product could be reduced to the monobrominated analog 50 in the presence of 0.96 equiv. Suitable bases include n-BuLi, 90 LDA, 91 LiHMDS, 92 and NaH. 77 Several researchers have utilized this methodology to obtain a-bromo and a,a-dibromophosphonoacetates on similar scaffolds with moderate to excellent yields.…”

Section: A-bromophosphonocarboxylates and Abromobisphosphonatesmentioning

confidence: 99%

“…Quenching the anion with an electrophilic bromine source subsequently provides the expected a-brominated phosphonocarboxylate and bisphosphonate analog. Suitable bases include n-BuLi, 90 LDA, 91 LiHMDS, 92 and NaH. 68,81,[93][94][95] The McKenna group was able to develop a-halo derivatives of a-hydroxy compounds 53a and 53b (Scheme 15), which are known anti-osteoporotic agents that act through blockage of prenylation.…”

Section: A-bromophosphonates On a Carbohydrate Scaffoldmentioning

confidence: 99%

Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres

Downey

Cairo

2014

Med. Chem. Commun.

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Substrate phosphorylation is a key modulator of signal transduction. Abnormal phosphorylation in vivo is implicated in many diseases including cancer, diabetes, and Alzheimer's disease. Inhibitors of phosphaterecognizing proteins have potential as medicinal agents as well as tools to study phosphorylation pathways. A well-known and common inhibition strategy is to synthetically replace the labile phosphate moiety with a non-hydrolyzable phosphonate. Fully saturated, a-fluoro and a,a-difluorophosphonates are often effective phosphate bioisosteres and have been well studied. More recently a-brominated phosphonates have begun to emerge as inhibitors of phosphate recognizing enzymes, some of which operate by irreversible mechanisms. Herein we discuss the synthetic approaches to aliphatic and benzylic a-bromophosphonates and their biological activities.Scheme 5 The synthesis of an aliphatic a-bromophosphonate derivative. 52 Scheme 6 An improved synthetic strategy to alkyl abromophosphonates. 53This journal is

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