34670-53-6

Upstream product

• 1605-65-8 N,N,N',N'-Tetramethylphosphorodiamidic chloride 
• 109-76-2 Trimethylenediamine 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 2524-04-1 diethyl phosphorochloridothioate 
• 4712-55-4 diphenyl hydrogen phosphite 

Downstream Products

• 16456-52-3 2-phenoxy-[1,3,2]diazaphosphinane 2-oxide 
• 108-95-2 phenol 

Relevant academic research and scientific papers

A new tricomponent reaction for the synthesis of symmetric and asymmetric alkyl bisphosphoramidates

A novel three-component one-pot reaction procedure was designed for the synthesis of symmetric and asymmetric bisphosphoramidate derivatives. Our key reactants were a set of four aliphatic diamines, which individually react with two different phosphoryl chloride derivatives (N,N,N′,N′-tetramethylphosphorodiamide chloride and diphenyl phosphoryl chloride). A total of 10 products, six of them none reported before, were synthetized. The proposed experimental procedure does not involve any catalyst and proceeds under routine experimental conditions (room temperature and 1 atm). Each synthesized compound was characterized by NMR (1H, 13C, and 31P) spectroscopy and mass spectrometry.

Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction

We present a new single-step multicomponent reaction strategy for the synthesis of symmetric and (novel) asymmetric bisphosphoramidate and bisphosphoramidothioate derivatives. Reactions proceed under routine experimental conditions, do not require the aid of any catalyst, and provide moderate yields after a short time. We synthesized 18 different compounds, 10 of them for the first time. The cytotoxic activity of our adducts was assessed by measuring their inhibitory capacity (IC50) against two different cell lines, the A549 (lung cancer cells) and the SW1353 (chondrosarcoma cells).

Characterizing the thermal degradation mechanism of two bisphosphoramidates by TGA, DSC, mass spectrometry and first-principle theoretical protocols

The present investigation describes a combined experimental-theoretical strategy to assess the thermal resistance features of two symmetric bisphosphoramidates, tetraphenyl ethane-1,2-diylbis (phosphoramidate) 1 and tetraphenyl propane-1,3-diylbis (phosphoramidate) 5. Therefore, their structural reluctance to thermal decomposition through differential scan calorimetric (DSC) and thermogravimetric (TGA) experiments was evaluated. Then, their molecular degradation path was followed by analysing recorded data from mass spectrometry measurements performed at different temperature conditions. Their corresponding thermal degradation mechanism was then established by searching plausible transition states interconnecting the intermediaries found in our mass spectrometry records using a quantum theoretical protocol based on Coupled-Cluster calculations. Through this strategy, key intermediaries of the two bisphosphoramidates studied during their molecular degradation mechanism were identified, although compound 5 displayed the highest resistance to heat decomposition.

Synthesis, crystal structure and biological evaluation of new phosphoramide derivatives as urease inhibitors using docking, QSAR and kinetic studies

In an attempt to achieve a new class of phosphoramide inhibitors with high potency and resistance to the hydrolysis process against urease enzyme, we synthesized a series of bisphosphoramide derivatives (01–43) and characterized them by various spectroscopic techniques. The crystal structures of compounds 22 and 26 were investigated using X-ray crystallography. The inhibitory activities of the compounds were evaluated against the jack bean urease and were compared to monophosphoramide derivatives and other known standard inhibitors. The compounds containing aromatic amines and their substituted derivatives exhibited very high inhibitory activity in the range of IC50 = 3.4–1.91 × 10?10 nM compared with monophosphoramides, thiourea, and acetohydroxamic acid. It was also found that derivatives with P[dbnd]O functional groups have higher anti-urease activity than those with P[dbnd]S functional groups. Kinetics and docking studies were carried out to explore the binding mechanism that showed these compounds follow a mixed-type mechanism and, due to their extended structures, can cover the entire binding pocket of the enzyme, reducing the formation of the enzyme-substrate complex. The quantitative structure-activity relationship (QSAR) analysis also revealed that the interaction between the enzyme and inhibitor is significantly influenced by aromatic rings and P[dbnd]O functional groups. Collectively, the data obtained from experimental and theoretical studies indicated that these compounds can be developed as appropriate candidates for urease inhibitors in this field.