1112-29-4

Usage

Uses

Used in Pharmaceutical Industry:
Tetraethyl(ethoxycarbonylethylidene)bisphosphonate is used as a potential treatment for bone diseases for its capacity to inhibit bone resorption and promote bone mineralization. This makes it a valuable asset in the development of new therapies aimed at strengthening and protecting bones, particularly for conditions like osteoporosis and Paget's disease.
Used in Bone Health Management:
In the realm of bone health, Tetraethyl(ethoxycarbonylethylidene)bisphosphonate is utilized to prevent bone loss, a critical factor in maintaining the structural integrity and functionality of the skeletal system. Its role in bone mineralization further underscores its importance in the management and treatment of bone disorders.
Used in Research and Development:
Tetraethyl(ethoxycarbonylethylidene)bisphosphonate is also used as a subject of research for understanding its mechanisms of action and potential side effects. This research is vital for refining its application and optimizing its use in clinical settings, ensuring the safety and efficacy of treatments that incorporate Tetraethyl(ethoxycarbonylethylidene)bisphosphonate.

Upstream product

• 23332-36-7 P,P'-methanediyl-bis-phosphonic acid tetraethyl ester; sodium salt 
• 105-39-5 chloroacetic acid ethyl ester 
• 78626-48-9 ethyl α-acetoxy-β-chlorolactate 
• 122-52-1 triethyl phosphite 
• 1660-94-2 Tetraethyl methylenediphosphonate 
• 105-36-2 ethyl bromoacetate 
• 762-04-9 phosphonic acid diethyl ester 
• 623-47-2 propynoic acid ethyl ester 
• 40149-32-4 ethyl 3-chloro-2-hydroxypropanoate 
• 762-04-9 Diethyl phosphonate 

Downstream Products

• 151869-73-7 3,3-bis(diethylphosphono)propanoic acid 

Relevant academic research and scientific papers

Role of base catalysts upon the Pudovik reaction: Unexpected synthesis of 1,2-dihydropyridine phosphonate derivatives

The role of base catalysts (CsNaX zeolite, hydrotalcite, triethylamine and pyridine derivatives) upon the regioselectivity of the Pudovik reaction is studied. The unexpected synthesis of stable 1,2-dihydropyridine phosphonate derivatives via a one-pot addition reaction under mild conditions is described.

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

Bisphosphonic acids (or bisphosphonates) have been successfully used in the clinic treatment of bone diseases for over decades. Additionally, the antiinflammatory activity of these compounds has been gaining attention. In our previous work, we synthesized and in vivo evaluated the bisphosphonic esters 1 and 2, finding a moderate edema inhibition upon oral and topical administration on BALB/c mice. Thus, in this work, the bioisosteric replacement of an amide functional group for an ester afforded the new bisphosphonates 3–6, which had a moderate oral edema inhibition (25 mg/kg dose) and a significant topical antiinflammatory activity (2 mg/ear) on BALB/c mice, with 6 being the most active hit (55.9% edema inhibition), comparable to the positive control (55.5% edema inhibition) on a TPA topical model. Next, to assess the acute toxicity of the synthesized derivatives, test animals were administered with 50–100 mg/kg of 3–6, respectively, by an oral route, and after 14 days, neither lethality nor a significative weight loss were observed. Finally, a structure–activity relationship (SAR) and a molecular docking analysis of 3–6 helped us to explain the trend observed in biological tests. Considering all these aspects, we propose the inhibition of MMP-8 and MMP-9 as a possible action mechanism of the synthesized derivatives.

Dual Radical/Polar Pudovik Reaction: Application Field of New Activation Methods

The Pudovik reaction (addition of organophosphorus compounds containing a labile P-H bond with alkenes and alkynes) can progess via a radical or (and) ionic mechanism. A comparative and systematic study including various reagents and different activation methods (heating, photochemical or ultrasonic irradiation, and dry medium supported reactions) is presented. Photolysis is the most efficient method for the radical processes, but in a few examples, ultrasonic irradiation can be more appropriate since the reaction time is shorter and ultrasound did not induce side-reactions (in particular Z/E isomerization). Dry medium process on basic solid support is the best anionic activation (yield, time, selectivity, purification facilities). Ultrasound, by its mechanical effects, can contribute to increase yield compared to the classical thermal method under these basic conditions. All the activation methods are efficient whatever the unsaturated substrates for the phosphine reactivity, whereas the appropriate activation method is exclusively determined by the nature of the unsaturated system for the thiophosphine (or phosphine oxide) reactivity.

SYNTHESE DE CONJUGUES GEM-BISPHOSPHONIQUES DE DERIVES DE LA CORTISONE

Some gem-bisphosphonic cortico-steroid conjugates are prepared by esterification between gem-bisphosphonate carboxylic acids and steroid primary alcohols.These original products take place in a biological study about a delivery-targeting concept of active constituents in bone therapy, with the assistance of gem-bisphosphonic building-blocks. Key words: gem-bisphosphonate; gem-bisphosphonic; tetraethyl ethylidene gem-bisphosphonate; corticosteroids; esterification; anti-inflammatory; delivery-targeting concept.

REACTION OF TRIETHYL PHOSPHITE WITH β-CHLOROLACTIC ACID DERIVATIVES

The reaction of equimolar amounts of triethyl phosphite with ethyl β-chlorolactate and its α-acetoxy derivative at 160-170 deg C affords ethyl β,β-bis(diethoxyphosphoryl)propionate.The additional recovery of diethyl α-(ethoxycarbonyl)ethyl phosphate in the case of the β-chlorolactate ester can be explained by partial thermal decomposition of the Arbuzov-rearrangement product that forms in the first step.