171503-10-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 762-04-9 phosphonic acid diethyl ester 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 7465-87-4 N-benzyl-4-methoxybenzamide 
• 622-72-0 N-(4-methoxylbenzylidene)benzylamine 

Downstream Products

• 171502-96-8 (C₆H₅)3GeCH₂CH₂C(O)N(CH₂C₆H₅)(CHC₆H₄OCH₃)(P(O)(OCH₂CH₃)2) 
• 110470-34-3 diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate 

Relevant academic research and scientific papers

Phosphorus-nitrogen system biology based flame retardant as well as synthesis method and application thereof

The invention discloses a phosphorus-nitrogen system biology based flame retardant as well as a synthesis method and application thereof. The method comprises the following steps: completely dissolving a raw material 1 into an organic solvent at room temp

Pharmacophore Mapping of Thienopyrimidine-Based Monophosphonate (ThP-MP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase

The human farnesyl pyrophosphate synthase (hFPPS), a key regulatory enzyme in the mevalonate pathway, catalyzes the biosynthesis of the C-15 isoprenoid farnesyl pyrophosphate (FPP). FPP plays a crucial role in the post-translational prenylation of small GTPases that perform a plethora of cellular functions. Although hFPPS is a well-established therapeutic target for lytic bone diseases, the currently available bisphosphonate drugs exhibit poor cellular uptake and distribution into nonskeletal tissues. Recent drug discovery efforts have focused primarily on allosteric inhibition of hFPPS and the discovery of non-bisphosphonate drugs for potentially treating nonskeletal diseases. Hit-to-lead optimization of a new series of thienopyrimidine-based monosphosphonates (ThP-MPs) led to the identification of analogs with nanomolar potency in inhibiting hFPPS. Their interactions with the allosteric pocket of the enzyme were characterized by crystallography, and the results provide further insight into the pharmacophore requirements for allosteric inhibition.

Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions

Magnetic-nanoparticle-supported phosphotungstic acid has been used to efficiently catalyze the hydrophosphonylation reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α-hydroxy and α-amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle was proposed.

Cleavage of phosphorus-carbon (P-C) bonds of α-amino phosphonates with intramolecular hydrogen migration in the gas phase using electrospray ionization tandem mass spectrometry

RATIONALE α-Amino phosphonates with intrinsic biological activities have been used in a wide variety of applications. Because of the widespread existence of natural organophosphorus compounds containing P-C bonds such as the α-amino phosphonates, it is important to investigate the gas-phase chemistry of P-C bonds in order to determine their basic properties, which might provide some insights into their biosynthesis and catalytic cleavage. METHODS Twenty α-amino phosphonates were successfully synthesized and their fragmentation behavior was systematically investigated using in-solution deuterium labeling in combination with high-resolution Fourier transform ion cyclotron resonance (FTICR) electrospray ionization tandem mass spectrometry. RESULTS The fragmentation pathways of twenty α-amino phosphonates with different chemical structures were systematically studied. In general, P-C bonds could be easily cleaved via a novel intramolecular hydrogen atom migration from the amino group to the phosphoryl group through a five-membered-ring intermediate in the gas phase. A possible mechanism of the rearrangement of α-amino phosphonates is proposed. CONCLUSIONS An interesting intramolecular hydrogen atom migration between the amino and phosphoryl groups was observed with cleavage of the P-C bond in the molecule through a five-membered-ring intermediate. This characteristic fragmentation pathway not only provides some insights into the basic chemistry of compounds with P-C bonds, but could also have some applications in the structural determination of the α-amino phosphonate analogues. Copyright

Direct transformation of amides into α-amino phosphonates via a reductive phosphination process

The first general method for the reductive phosphination of amides in one pot has been developed. The reactions described provide a novel access to α-amino phosphonates in good to excellent yields, cover a broad scope of substrates such as secondary and tertiary amides, and do not require a low temperature.

SYNTHESIS AND ANTITUMOR ACTIVITY OF NOVEL &α-SUBSTITUTED AMINOMETHYLPHOSPHONATES

Two series of novel α-substituted aminomethyl phosphonates (1) and (2) have been synthesized and the reaction conditions are discussed.All the products have been confirmed by 1H NMR, IR spectra and elemental analysis, and x-ray diffraction.The bioassay showed that some of the compounds inhibit the growth of the leukemia L1210 cell in vitro.Key words: Aminomethylphosphonate; synthesis; antitumor activity; X-ray diffraction.