111072-49-2

Usage

Uses

Used in Chemical and Industrial Applications:
(thiomorpholin-4-ylmethanediyl)bis(phosphonic acid) is used as a chelating agent for its ability to form strong complexes with metal ions. This characteristic is valuable in various chemical processes and industrial applications where metal ion management is crucial.
Used in Corrosion Inhibition:
(thiomorpholin-4-ylmethanediyl)bis(phosphonic acid) is used as a corrosion inhibitor to protect metals from degradation. Its chelating properties enable it to bind to metal surfaces, creating a barrier that prevents further corrosion and extends the lifespan of metal structures.
Used in Water Treatment:
(thiomorpholin-4-ylmethanediyl)bis(phosphonic acid) is used as a water treatment agent to manage metal ion concentrations. By chelating with metal ions, it helps to control the levels of these ions in water, which can be beneficial for both industrial processes and environmental protection.
Used in Metal Complexation:
(thiomorpholin-4-ylmethanediyl)bis(phosphonic acid) is used as a metal complexation agent in the synthesis of various metal complexes. Its ability to bind with metal ions makes it a useful tool in the preparation of new materials with specific properties for applications in areas such as catalysis, electronics, and pharmaceuticals.

Upstream product

• 61907-20-8 N-formyl-thiomorpholine 
• 79-37-8 oxalyl dichloride 
• 123-90-0 Thiomorpholin 

Relevant academic research and scientific papers

Interactions of N-heteroalkylaminomethylenebisphosphonic acids with Cd(II) ions: Electrochemical and spectroscopic investigations

Abstract The aminomethylenebisphosphonates are known to be excellent chelators for many metal ions. In this work, the coordination properties of three different aminomethylenebisphosphonates with N-substituted heteroalkyl moieties (L1, L2 and L3) and their N-pyridyl derivative (L4) toward cadmium(II) ions are described. Due to their coordination abilities over a broad range of pH, the compounds of this group are good candidates for heavy metal detoxification. To determine the stability constants and the coordination mode of formed aminomethylenebisphosphonate-cadmium(II) complexes, four analytical methods were employed: potentiometry, pulse polarography (DPP), nuclear magnetic resonance spectroscopy (NMR) and electrospray ionization mass spectrometry (ESI-MS). The studies performed revealed that ligands L1, L2 and L3 possessed similar coordination properties, with Cd(II) ions binding below pH 2 to form equimolar complexes and above pH 6 to form bis-complexes. The ligand L4 behaved in a different way, forming six complexes of varied stoichiometry: CdH4L3, CdH3L3, CdHL2, CdL2, CdH2L and Cd3H4L3. The hypothetical competition plot between common complexone d-penicillamine and the studied ligands showed better complexation properties for the aminomethylenebisphosphonates in the pH range 2-6 than for neutral pH, where above neutral pH d-penicillamine bound Cd(II) ions significantly better.

Effects of Bisphosphonates on the Growth of Entamoeba histolytica and Plasmodium Species in Vitro and in Vivo

The effects of a series of 102 bisphosphonates on the inhibition of growth of Entamoeba histolytica and Plasmodium falciparum in vitro have been determined, and selected compounds were further investigated for their in vivo activity. Forty-seven compounds tested were active (IC50 50 ～ 4-9 μM) were nitrogen-containing bisphosphonates with relatively large aromatic side chains. Simple n-alkyl-1-hydroxy-1,1-bisphosphonates, known inhibitors of the enzyme farnesylpyrophosphate (FPP) synthase, were also active, with optimal activity being found with C9-C10 side chains. However, numerous other nitrogen-containing bisphosphonates known to be potent FPP synthase inhibitors, such as risedronate or pamidronate, had little or no activity. Several pyridine-derived bisphosphonates were quite active (IC50 ～ 10-20 μM), and this activity was shown to correlate with the basicity of the aromatic group, with activity decreasing with increasing pKa values. The activities of all compounds were tested versus a human nasopharyngeal carcinoma (KB) cell line to enable an estimate of the therapeutic index (TI). Five bisphosphonates were selected and then screened for their ability to delay the development of amebic liver abscess formation in an E. histolytica infected hamster model. Two compounds were found to decrease liver abscess formation at 10 mg/kg ip with little or no effect on normal liver mass. With P. falciparum, 35 compounds had IC50 values 50 values around 1 μM. Five compounds were again selected for in vivo investigation in a Plasmodium berghei ANKA BALB/c mouse suppressive test. The most active compound, a C9 n-alkyl side chain containing bisphosphonate, caused an 80% reduction in parasitemia with no overt toxicity. Taken together, these results show that bisphosphonates appear to be useful lead compounds for the development of novel antiamebic and antimalarial drugs.

3-D QSAR Investigations of the Inhibition of Leishmania major Farnesyl Pyrophosphate Synthase by Bisphosphonates

We report the activities of 62 bisphosphonatesas inhibitors of the Leishmania major mevalonate/isoprene biosynthesis pathway enzyme, farnesyl pyrophosphate synthase. The compounds investigated exhibit activities (IC 50 values) ranging from ～100 nM to ～80 μM (corresponding to Ki values as low as 10 nM). The most active compounds were found to be zoledronate (whose single-crystal X-ray structure is reported), pyridinyl-ethane-1-hydroxy-1,1-bisphosphonates or picolyl aminomethylene bisphosphonates. However, N-alicyclic amino-methylene bisphosphonates, such as incadronate (N-cycloheptyl aminomethylene bisphosphonate), as well as aliphatic aminomethylene bisphosphonates containing short (n = 4, 5) alkyl chains, were also active, with 1C50 values in the 200-1700 nM range (corresponding to Ki values of ～20-170 nM). Bisphosphonates containing longer or multiple (N,N-) alkyl substitutions were inactive, as were aromatic species lacking an o- or m-nitrogen atom in the ring, or possessing multiple halogen substitutions or a p-amino group. To put these observations on a more quantitative structural basis, we used three-dimensional quantitative structure-activity relationship techniques: comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA), to investigate which structural features correlated with high activity. Training set results (N = 62 compounds) yielded good correlations with each technique (R2 = 0.87 and 0.88, respectively), and were further validated by using a training/test set approach. Test set results (N = 24 compounds) indicated that IC50 values could be predicted within factors of 2.9 and 2.7 for the CoMFA and CoMSIA methods, respectively. The CoMSIA fields indicated that a positive charge in the bisphosphonate side chain and a hydrophobic feature contributed significantly to activity. Overall, these results are of general interest since they represent the first detailed quantitative structure-activity relationship study of the inhibition of an expressed farnesyl pyrophosphate synthase enzyme by bisphosphonate inhibitors and that the activity of these inhibitors can be predicted within about a factor of 3 by using 3D-QSAR techniques.

Bisphosphonic acid derivatives, their production and use

Novel compounds of the formula I STR1 in which R 1 -R 11 can be the same or different and stand for hydrogen, a straight or branced aliphatic or alicyclic C 1 -C 10 hydrocarbon radical, an aryl or an aryl-C 1 -C 4 -alkyl radical; n is zero or one, and m i