78906-56-6

Upstream product

• 19172-47-5 Lawessons reagent 
• 100-46-9 benzylamine 

Downstream Products

• 78906-66-8 N,N'-dibenzyl-4-methoxyphenylphosphonothioic diamide 
• 78906-72-6 S-benzyl N-benzyl-4-methoxyphenylphosphonamidodithioate 

Relevant academic research and scientific papers

Synthesis and structural characterization of Pd(II) and Cu(I) complexes containing dithiophosphorus ligand and their catalytic activities for Heck reaction

2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) was made to react with benzylamine to produce [(PhCH2NH)(p-C6H4OMe)PS2]?[PhCH2NH3]+in a very facile manner. From the abovementioned product, two new complexes {Pd[(PhCH2NH)(p-C6H4OMe)PS2]2} (C1) and {Cu2(PPh3)2[(PhCH2NH)(p-C6H4OMe)PS2]2} (C2) were obtained in high yields whose molecular structures were ascertained by X-ray diffraction analysis, IR and NMR spectroscopy, and elemental analysis. The catalytic properties of both complexes were evaluated in the Heck reaction. High turnover numbers (TONs) and yields were observed for palladium catalyst and it was revealed that dicopper(I) complex by a distance of 2.84?? between metal ions, bearing triphenylphosphine and dithiophosphorus ligands, can catalyze the Heck reaction. This is the first report of Cu(I) complex as catalyst in the Heck reaction. Natural bonding orbital (NBO) analysis for C1 indicated that natural charge on Pd atom is ?0.07e and Pd atom has formed four sigma bonds with S atoms. Similarly, NBO analysis revealed no significant Cu?Cu interaction in dicopper complex C2.

Antibacterial activity of amidodithiophosphonato nickel(II) complexes: An experimental and theoretical approach

The reactions of 2,4-bis(4-methoxyphenyl)-1,3-dithio-2,4-diphosphetane-2,4-disulfide (Lawesson’s Reagent, LR) with benzylamine (BzNH2) and 4-phenylbutylamine (PhBuNH2) yield benzylammonium P-(4-methoxyphenyl)-N-benzyl-amidodithiophosphonate (BzNH3)(BzNH-adtp) and 4-phenylbutylammonium P-(4-methoxyphenyl)-N-(4-phenylbutyl)-amidodithiophosphonate (PhBuNH3)(PhBuNH-adtp). The relevant nickel complexes [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] and the corresponding hydrolysed derivatives (BzNH3)2[Ni(dtp)2] and (PhBuNH3)2[Ni(dtp)2] were prepared and fully characterized. The antimicrobial activity of the aforementioned amidodithiophosphonates against a set of Gram-positive and Gram-negative pathogen bacteria was evaluated, and [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] showed antiproliferative activity towards Staphylococcus aureus and Staphylococcus haemolyticus strains. density functional theory (DFT) calculations were performed to shed some light on the activity of reported compounds related to their tendency towards P–N bond cleavage.

Discovery of New H2S Releasing Phosphordithioates and 2,3-Dihydro-2-phenyl-2-sulfanylenebenzo[d][1,3,2]oxazaphospholes with Improved Antiproliferative Activity

Hydrogen sulfide (H2S) is now recognized as a physiologically important gasotransmitter. Compounds which release H2S slowly are sought after for their potential in therapy. Herein the synthesis of a series of phosphordithioates based on 1 (GYY4137) are described. Their H2S release profiles are characterized using 2,6-dansyl azide (2), an H2S specific fluorescent probe. Most compounds have anticancer activity in several solid tumor cell lines and are less toxic in a normal human lung fibroblast, WI38. A preferred compound, 14, with 10-fold greater anticancer activity than 1, was shown to release H2S in MCF7 cells using a cell active probe, 21. Both permeability and intracellular pH (pHi) were found to be significantly improved for 14 compared to 1. Furthermore, 14 was also negative in the AMES test for genotoxicity. Cyclization of these initial structures gave a series of 2,3-dihydro-2-phenyl-2-sulfanylenebenzo[d][1,3,2]oxazaphospholes, of which the simplest member, compound 22 (FW1256), was significantly more potent in cells. The improved therapeutic window of 22 in WI38 cells was compared with three other cell types. Potency of 22 was superior to 1 in MCF7 tumor spheroids and the mechanism of cell death was shown to be via apoptosis with an increase in cleaved PARP and activated caspase-7. Evidence of H2S release in cells is also presented. This work provides a "toolbox" of slow-release H2S donors useful for studies of H2S in biology and as potential therapeutics in cancer, inflammation, and cardiovascular disease. (Chemical Equation Presented).

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS - XXXV. A NEW ROUTE TO 4-METHOXYPHENYLPHOSPHONOTHIOIC DIAMIDES FROM 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE AND AMINES

By reacting primary and secondary amines with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 1A, at 25 deg C ammonium 4-methoxyphenylphosphonamidodithioates, 2, are formed.Upon heating to 140 deg C 2 eliminates hydrogen sulfide in a new type of reaction yielding 4-methoxyphenylphosphonothioic diamides, 3, which also are formed directly from primary amines and 1A at 140 deg C.For dibenzylamine some anomalous results are observed due to N->S rearrangement reactions.NMR spectroscopic data are presented for compounds 2 and 3.