Imidazolinone
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Imidazolinone
Imidazolidinones or imidazolinones are a class of 5-membered ring heterocycles structurally related to imidazole. Imidazolidinones feature a saturated C3N2 nucleus, except for the presence of a urea or amide functional group in the 2 or 4 positions. 2-Imidazolidinones The 2-imidazolidinones are cyclic derivatives of urea. 1,3-Dimethyl-2-imidazolidinone is a polar solvent and Lewis base. Drugs featuring this ring system include emicerfont, imidapril, and azlocillin. Dimethylol ethylene urea is the reagent used in permanent press clothing. 4-Imidazolidinones 4-Imidazolidinones can be prepared from phenylalanine in two chemical steps (amidation with methylamine followed by condensation reaction with acetone): Imidazolidinone catalyst work by forming an iminium ion with carbonyl groups of α,β-unsaturated aldehydes ( enals) and enones in a rapid chemical equilibrium. This iminium activation lower the substrate's LUMO. Several 4-imidazolidinones have been investigated. Dru ...
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Imidazolinone Herbicide
Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. This organic compound is used to control a broad spectrum of weed species. It is a colorless or white solid, although commercial samples can appear brown or tan. Imidazolinone herbicides Imazaquin along with imazamethabenz-methyl, imazapyr, imazapic, imazethapyr, and imazamox comprise the class of synthetic compounds termed the imidazolinone herbicides. These chemicals all feature an imidazolinone ring with a carboxylic acid group attached to the backbone. They vary in the attached ring structure. Imidazolinone herbicides kill plants by inhibiting acetohydroxy acid synthase (AHAS). AHAS is the first enzyme in the branched-chain amino acid pathway that leads to the synthesis of amino acids leucine, isoleucine, and valine. Crop varieties have been developed through conventional breeding that are resistant to these herbicides and are marketed by BASF under the Clearfield brand. History ...
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Imazaquin
Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. This organic compound is used to control a broad spectrum of weed species. It is a colorless or white solid, although commercial samples can appear brown or tan. Imidazolinone herbicides Imazaquin along with imazamethabenz-methyl, imazapyr, imazapic, imazethapyr, and imazamox comprise the class of synthetic compounds termed the imidazolinone herbicides. These chemicals all feature an imidazolinone ring with a carboxylic acid group attached to the backbone. They vary in the attached ring structure. Imidazolinone herbicides kill plants by inhibiting acetohydroxy acid synthase (AHAS). AHAS is the first enzyme in the branched-chain amino acid pathway that leads to the synthesis of amino acids leucine, isoleucine, and valine. Crop varieties have been developed through conventional breeding that are resistant to these herbicides and are marketed by BASF under the Clearfield brand. History T ...
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Carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl). The remainder of this article concerns itself with the organic chemistry definition of carbonyl, where carbon and oxygen share a double bond. Carbonyl compounds In organic chemistry, a carbonyl group characterizes the following types of compounds: Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide. ...
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Histidine
Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also. It is encoded by the codons CAU and CAC. Histidine was first isolated by Albrecht Kossel and Sven Gustaf Hedin in 1896. It is also a precursor to histamine, a vital inflammatory agent in immune responses. The acyl radical is histidyl. Properties of the imidazole side chain The conjugate acid (protonated form) of the imidazole side chain in histidine has a p''K''a of approximately 6.0. Thus, below a pH of 6, the imidazole ring ...
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Imidazol-4-one-5-propionic Acid
Imidazol-4-one-5-propionic acid is an intermediate in the metabolism of histidine. It is a colorless compound that is sensitive to light in air. The compound features an imidazolone ring. Occurrence It arises via the action of urocanase on urocanic acid. Hydrolysis of the heterocycle to the glutamic acid derivative is catalyzed by imidazolonepropionate hydrolase. Microbial production of imidazol-4-one-5-propionic acid in the human gut has been shown to affect insulin signaling, which is relevant to type II diabetes. See also * Formiminoglutamic acid Formiminoglutamic acid (FIGLU; conjugate base, formiminoglutamate) is an intermediate in the catabolism of L-histidine to L-glutamic acid. It thus is also a biomarker for intracellular levels of folate. The FIGLU test is used to identify vitam ... * Urocanate * Urocanate hydratase References Carboxylic acids Imidazolines Lactams {{heterocyclic-stub ...
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Imidazoline
Imidazoline is a class of heterocycles formally derived from imidazoles by the reduction of one of the two double bonds. Three isomers are known, 2-imidazolines, 3-imidazolines, and 4-imidazolines. The 2- and 3-imidazolines contain an 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 bo ... center, whereas the 4-imidazolines contain an alkene group. The 2-Imidazoline group occurs in several drugs.Liu, H. and Du, D.-M. (2009), Recent Advances in the Synthesis of 2-Imidazolines and Their Applications in Homogeneous Catalysis. Adv. Synth. Catal., 351: 489–519. doi: 10.1002/adsc.200800797 References {{Organic-chemistry-stub ...
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Spiroxatrine
Spiroxatrine is a drug which acts as a selective antagonist at both the 5-HT1A receptor and the α2C adrenergic receptor. It is an analog of spiperone and also has some dopamine antagonist A dopamine antagonist, also known as an anti-dopaminergic and a dopamine receptor antagonist (DRA), is a type of drug which blocks dopamine receptors by receptor antagonism. Most antipsychotics are dopamine antagonists, and as such they have ... effects. References 5-HT1A antagonists Abandoned drugs Alpha-2 blockers Benzodioxans Dopamine antagonists Imidazolidinones Spiro compounds {{Nervous-system-drug-stub ...
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Spiperone
Spiperone (Spiroperidol; brand name: Spiropitan ( JP)) is a typical antipsychotic and research chemical belonging to the butyrophenone chemical class. It is licensed for clinical use in Japan as a treatment for schizophrenia. Additionally, spiperone was identified by compound screening to be an activator of Ca2+ activated Cl− channels (CaCCs), thus a potential target for therapy of cystic fibrosis. ''N''-Methylspiperone (NMSP) is a derivate of spiperone that is used to study the dopamine and serotonin neurotransmitter system. Labeled with the radioisotope carbon-11, it can be used for positron emission tomography. References {{Navboxes , title = Pharmacodynamics Pharmacodynamics (PD) is the study of the biochemical and physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or combinations of organisms (fo ... , titlestyle = background:#ccccff , list1 = {{Adrenergi ...
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NNC 63-0532
NNC 63-0532 is a nociceptoid drug used in scientific research. It acts as a potent and selective agonist for the nociceptin receptor, also known as the ORL-1 ( opiate receptor-like 1) receptor. The function of this receptor is still poorly understood, but it is thought to have roles in many disorders such as pain, drug addiction, development of tolerance to opioid drugs, and psychological disorders such as anxiety and depression. Research into the function of this receptor is an important focus of current pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and re ... development, and selective agents such as NNC 63-0532 are essential for this work. References Opioids 1-Naphthyl compounds Piperidines Methyl esters Spiro compounds Imidazolidinones Nociceptin recept ...
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Hetacillin
Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and has no antibacterial activity itself, but quickly splits off acetone in the human body to form ampicillin, which is active against a variety of bacteria. __TOC__ Administration Hetacillin can be administered orally. The potassium salt, hetacillin potassium, is administered by injection, either intravenously or intramuscularly. It is sold under the trade name Hetacin for intramammary injection in veterinary use. Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin. Chemistry Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at and pH 7, quickly releasing acetone again. As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least ''in vitro ''In vitro'' (meaning in gla ...
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LUMO
In chemistry, HOMO and LUMO are types of molecular orbitals. The acronyms stand for ''highest occupied molecular orbital'' and ''lowest unoccupied molecular orbital'', respectively. HOMO and LUMO are sometimes collectively called the ''frontier orbitals'', such as in the frontier molecular orbital theory. Gap The energy difference between the HOMO and LUMO is ''the HOMO–LUMO gap''. Its size can be used to predict the strength and stability of transition metal complexes, as well as the colors they produce in solution.Griffith, J. S. and L. E. Orgel"Ligand Field Theory" ''Q. Rev. Chem. Soc.'' 1957, 11, 381–383. As a rule of thumb, the larger a compound's HOMO-LUMO gap, the more stable the compound. Semiconductors The HOMO level is to organic semiconductors roughly what the maximum valence band is to inorganic semiconductors and quantum dots. The same analogy can be made between the LUMO level and the conduction band minimum.Bredas, J,-L"Mind the gap!" ''Mater. Horiz.'' 2 ...
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Chemical Equilibrium
In a chemical reaction, chemical equilibrium is the state in which both the reactants and products are present in concentrations which have no further tendency to change with time, so that there is no observable change in the properties of the system. This state results when the forward reaction proceeds at the same rate as the reverse reaction. The reaction rates of the forward and backward reactions are generally not zero, but they are equal. Thus, there are no net changes in the concentrations of the reactants and products. Such a state is known as dynamic equilibrium. Historical introduction The concept of chemical equilibrium was developed in 1803, after Berthollet found that some chemical reactions are reversible. For any reaction mixture to exist at equilibrium, the rates of the forward and backward (reverse) reactions must be equal. In the following chemical equation, arrows point both ways to indicate equilibrium. A and B are reactant chemical species, S and T are p ...
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