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Aminophosphonate
Aminophosphonates are organophosphorus compounds with the formula (RO)2P(O)CR'2NR"2. These compounds are structural analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups. Acting as antagonists of amino acids, they inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell. These effects may be exerted as antibacterial, plant growth regulatory or neuromodulatory. They can act as ligands, and heavy metal complexes with aminophosphonates have had medical applications investigated. Phosphonates are more difficult to hydrolyse than phosphates. Preparation Aminophosphonates are often prepared by hydrophosphonylation, usually the condensation of imines and phosphorous acid. In the Pudovik reaction or Kabachnik–Fields reaction the esters of phosphorous acid are employed, e.g. diphenylphosphite. Because these compounds are of pharmaceutical interest, methods have been developed to induce the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Kabachnik–Fields Reaction
In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming aminophosphonate, α-aminomethylphosphonates from an amine, a carbonyl compound, and a phosphite ester, dialkyl phosphonate, (RO)2P(O)H (that are also called dialkylphosphites). Aminophosphonates are synthetic targets of some importance as phosphorus analog (chemistry), analogues of α-amino acids (a bioisosterism, bioisostere). This multicomponent reaction was independently discovered by and Ellis K. Fields in 1952. The reaction is very similar to the two-component Pudovik reaction, which involves condensation of the phosphite and a preformed imine. : The first step in this reaction is the formation of an imine, followed by a hydrophosphonylation step where the phosphonate P-H bond across the C=N double bond. The starting carbonyl component is usually an aldehyde and sometimes a ketone. The reaction can be accelerated with a combination of dehydrating reagent and Lewis acid ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diphenylphosphite
Diphenylphosphite is a diorganophosphite with the formula (C6H5O)2P(O)H. The molecule is tetrahedral. It is a colorless viscous liquid. The compounds can be prepared by treating phosphorus trichloride with phenol. Many analogues can be prepared similarly. One illustrative reaction, diphenylphosphite, aldehydes, and amines react to afford aminophosphonates (Kabachnik–Fields reaction).{{cite journal, title=An Extremely Efficient Three-Component Reaction of Aldehydes/Ketones, Amines, and Phosphites Kabachnik-Fields reaction for the Synthesis of α-Aminophosphonates Catalyzed by Magnesium Perchlorate, authors=Bhagat, Srikant; Chakraborti, Asit K., journal=Journal of Organic Chemistry, year=2007, volume=72, issue=4 , pages=1263–1270, doi=10.1021/jo062140i, pmid=17253748 See also *Dimethylphosphite *Diethylphosphite Diethylphosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organophosphorus Compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds. Phosphorus can adopt ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pudovik Reaction
In organophosphorus chemistry, the Pudovik reaction is a method for preparing α-aminomethylphosphonates. Under basic conditions, the phosphorus–hydrogen bond of a dialkylphosphite, (RO)2P(O)H, adds across the carbon–nitrogen double bond of an imine (a hydrophosphonylation reaction). The reaction is closely related to the three-component Kabachnik–Fields reaction, where an amine, phosphite, and an organic carbonyl compound are condensed, which was reported independently by Martin Kabachnik and Ellis Fields in 1952. In the Pudovik reaction, a generic imine, RCH=NR', would react with a phosphorous reagent like diethylphosphite as follows: :RCH=NR' + (EtO)2P(O)H → (EtO)2P(O)CHR-NHR' In addition to the Lewis-acid catalyzed Pudovik reaction, the reaction may be carried out in the presence of chiral amine bases. Catalytic amounts of quinine Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to ''Plasmod ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Quadramet
Samarium (153Sm) lexidronam (chemical name Samarium-153-ethylene diamine tetramethylene phosphonate, abbreviated Samarium-153 EDTMP, trade name Quadramet) is a chelated complex of a radioisotope of the element samarium with EDTMP. It is used to treat pain when cancer has spread to the bone. It is injected into a vein and distributed throughout the body, where it is preferentially absorbed in areas where cancer has invaded the bone. The radioisotope 153Sm, with a half-life of 46.3 hours, decays by emitting beta particles (electrons), which kill the nearby cells. Pain begins to improve in the first week for most people and the effects can last several months. It is commonly used in lung cancer, prostate cancer, breast cancer, and osteosarcoma. Side effects Side effects include the following: *Black, tarry stools *Blood in urine/stool *Cough, hoarseness *Fever/chills *Lower back/side pain *Painful or difficult urination *Pinpoint red spots on skin *Irregular heartbeat *Nause ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chelating
Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a Denticity, polydentate (multiple bonded) ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds, but this is not a necessity, as in the case of zinc and its use as a maintenance therapy to prevent the absorption of copper in people with Wilson's disease. Chelation is useful in applications such as providing nutritional supplements, in chelation therapy to remove toxic metals from the body, as contrast medium, contrast agents in MRI, MRI scanning, in manufacturing using homogeneous catalysts, in chemical water treatment to assist in the removal of metals, and in fertilizers. Chelate effect The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
EDTMP
EDTMP or ethylenediamine tetra(methylene phosphonic acid) is a phosphonic acid. It has chelate, chelating and anti corrosion properties. EDTMP is the phosphonate analog of EDTA.Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic," In 'Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008. {{doi, 10.1002/14356007.a19_545.pub2. It is classified as a nitrogenous organic polyphosphonic acid. Properties and applications EDTMP is normally delivered as its sodium salt, which exhibits good solubility in water. Used in Water treatment as an antiFouling, scaling and anti corrosion agent, the corrosion inhibition of EDTMP is 3–5 times better than that of inorganic polyphosphate. It has good chemical stability and thermal tolerance. It shows excellent scale inhibition ability under temperature 200 °C. It functions by chelating with many metal ions. The anti-cancer drug Samarium (153Sm) lexidronam, Samarium (153Sm) lexidronam is also derived fr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Glyphosate
Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum Herbicide, systemic herbicide and Crop desiccation, crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase. It is used to kill weeds, especially annual Forbs, broadleaf weeds and grasses that compete with crops. Its herbicidal effectiveness was discovered by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup (herbicide), Roundup. Monsanto's last commercially relevant United States patent expired in 2000. Farmers quickly adopted glyphosate for agricultural weed control, especially after Monsanto introduced glyphosate-resistant Roundup Ready crops, enabling farmers to kill weeds without killing their crops. In 2007, glyphosate was the most used herbicide in the United States' agricultural sector and the second-most use ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aminomethylphosphonic Acid
Aminomethylphosphonic acid (AMPA) is a weak organic acid with a phosphonic acid group. Application AMPA apparently can be used as biocide and pesticide. AMPA is also used in research to assess the exposure of glyphosate. Environmental fate AMPA is one of the primary degradation products of the herbicide glyphosate and the related chemical glyphosat-trimesium. AMPA has the potential to be broken down further by manganese oxide in laboratory conditions, however in soil manganese oxide is usually only present in trace amounts. Microbial degradation of AMPA is the more likely degradation pathway, where it degrades into phosphoric acid and ultimately to carbon dioxide and inorganic phosphate. Toxicity AMPA has toxicity which is comparable to that of glyphosate and it is therefore considered to be of similar toxicological concern (harmful in greater than 0.5 parts per million) as glyphosate itself. [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphorous Acid
Phosphorous acid (or phosphonic acid (singular)) is the compound described by the formula H3PO3. This acid is diprotic (readily ionizes two protons), not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids. Nomenclature and tautomerism H3PO3 is more clearly described with the structural formula HPO(OH)2. In the solid state, has tetrahedral geometry about the central phosphorus atom, with a P–H bond of 132 pm, one P=O double bond of 148 pm and two longer P–O(H) single bonds of 154 pm. This species exists in equilibrium with an extremely minor tautomer . IUPAC recommends that the latter be called phosphorous acid, whereas the dihydroxy form is called phosphonic acid.. Only the reduced phosphorus compounds are spelled with an "ous" ending. Other important oxyacids of pho ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amino Acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha amino acids appear in the genetic code. Amino acids can be classified according to the locations of the core structural functional groups, as Alpha and beta carbon, alpha- , beta- , gamma- or delta- amino acids; other categories relate to Chemical polarity, polarity, ionization, and side chain group type (aliphatic, Open-chain compound, acyclic, aromatic, containing hydroxyl or sulfur, etc.). In the form of proteins, amino acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions. Structure For ketimines and aldimines, respectively, the five core atoms (C2C=NX and C(H)C=NX, X = H or C) are coplanar. Planarity results from the sp2-hybridization of the mutually double-bonded carbon and the nitrogen atoms. The C=N distance is 1.29-1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C-N distances in amines and nitriles are 1.47 and 1.16 Å, respectively. Rotation about the C=N bond is slow. Using NMR spectroscopy, both E- and Z-isomers of aldimines have been detected. Owing to steric effects, the E isomer is favored. Nomenclature and classification The term "imine" was coine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
