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Indol
Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin. General properties and occurrence Indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many perfumes. It also occurs in coal tar. The corresponding substituent is called indolyl. Indole undergoes electrophilic substitution, mainly at position 3 (see diagram ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indoline
Indoline is an aromatic heterocyclic organic compound with the chemical formula C8H9N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound is based on the indole structure, but the 2-3 bond is saturated Saturation, saturated, unsaturation or unsaturated may refer to: Chemistry * Saturation, a property of organic compounds referring to carbon-carbon bonds **Saturated and unsaturated compounds **Degree of unsaturation **Saturated fat or fatty acid .... By oxidation/dehydrogenation it can be converted to indoles. Indoline was used to make Indocaine. References {{heterocyclic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isatin
Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids. Isatin is a well-known natural product which can be found in plants of the genus '' Isatis'', in '' Couroupita guianensis'', and also in humans, as a metabolic derivative of adrenaline. It looks like a red-orange powder, and it is usually employed as building block for the synthesis of a wide variety of biologically active compounds including antitumorals, antivirals, anti-HIVs, and antituberculars. The isatin core is also responsible for the color of “ Maya blue” and “Maya yellow” dyes. Synthesis Sandmeyer methodology The Sandmeyer methodology is the oldest and straightforward way for the synthesis of isatin. The method involves the condensation between chloral hydrate and a primary arylamine (e.g. ani ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indolium
Indolium is a cation with molecular formula C8H8N+, and forms chemical compounds in combination with anions. It is an onium ion derived from its parent compound, indole Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environme ..., by the addition of a proton. References Indoles {{heterocyclic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Oxindole
Oxindole (2-indolone) is an aromatic heterocyclic organic compound with the formula C6H4CHC(O)NH. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Oxindole is a modified indoline with a substituted carbonyl at the second position of the 5-member indoline ring. Classified as a cyclic amide, it is a pale yellow solid. Formation and reactions Oxindole is derived in nature from tryptophan, formed by gut bacteria ("normal flora"). It is normally metabolized and detoxified from the body by the liver. In excess, it can cause sedation, muscle weakness, hypotension, and coma. Patients with hepatic encephalopathy have been recorded to have elevated serum oxindole levels. Treatment with phosphorus pentasulfide Phosphorus pentasulfide is the inorganic compound with the formula ( monomer) or ( dimer). This yellow solid is the one of two phosphorus sulfides of commercial value. Samples often appear greenish-gray du ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Skatole
Skatole or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary contributor to fecal odor. In low concentrations, it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and '' Ziziphus mauritiana''. It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name derives from the Greek root ''skato-'', meaning feces. Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849–1919). Original: "''Ich habe mich zuerst mit der Untersuchung der flüchtigen Bestandtheile der Excremente aus sauerer Lösung beschäftigt. Es wurden dabei die flüchtigen Fettsäuren: Essigsäure, normale und Isobuttersäure, sowie die aromatischen Substanzen: Phenol, Indol und eine neue dem Indol verwandte Substanz, die ich Skatol nennen werde, erhalten."'' ----''Translation'': "I was occupied ini ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indene
Indene is a flammable polycyclic hydrocarbon with chemical formula . It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins. Substituted indenes and their closely related indane derivatives are important structural motifs found in many natural products and biologically active molecules, such as sulindac. Isolation Indene occurs naturally in coal-tar fractions boiling around 175–185 °C. It can be obtained by heating this fraction with sodium to precipitate solid "sodio-indene". This step exploits indene's weak acidity evidenced by its deprotonation by sodium to give the indenyl derivative. The sodio-indene is converted back to indene by steam distillation. Reactivity Indene readily polymerises. Oxidation of indene with acid dichromate yields homophthalic acid (''o''-carboxylp ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzophosphole
Benzophosphole is the organic compound with the chemical formula C8H7P; it is the phosphorus analog of indole. The term benzophosphole also refers to substituted derivatives of the parent heterocycle. See also * Organophosphorus chemistry * Phosphole * Indole Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environme ... References {{Simple aromatic rings Phosphorus heterocycles Heterocyclic compounds with 2 rings Simple aromatic rings ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzofuran
Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Production Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol. Laboratory methods Benzofurans can be prepared by various methods in the laboratory. Notable examples include: *''O''-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation. *Perkin rearrangement, where a coumarin is reacted with a hydroxide: : *Diels–Alder reaction of nitro vinyl furans with various dienophiles: : Diels–Alder reaction yielding a substituted benzofuran, 450px *Cycloisomerization of alkyne ortho-substituted phenols: : Benzofurans via Cycloisomerization, 400px Related compo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbazole
Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole structure, but in which a second benzene ring is fused onto the five-membered ring at the 2–3 position of indole (equivalent to the 9a–4a double bond in carbazole, respectively). Carbazole is a constituent of tobacco smoke. Synthesis A classic laboratory organic synthesis for carbazole is the Borsche–Drechsel cyclization. In the first step, phenylhydrazine is condensed with cyclohexanone to the corresponding imine. The second step is a hydrochloric acid-catalyzed rearrangement reaction and ring-closing reaction to tetrahydrocarbazole. In one modification, both steps are rolled into one by carrying out the reaction in acetic acid. In the third step, this compound is oxidized by red lead to carbazole itself. Another classi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aromatic Compound
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties are understood. The current definition of aromatic compounds does not have any relation with their smell. Heteroarenes are closely related, since at least one carbon atom of CH group is replaced by one of the heteroatoms oxygen, nitrogen, or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Benzene ring model Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one named as su ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carboline
β-Carboline (9''H''- pyrido ,4-''b'' ndole) represents the basic chemical structure for more than one hundred alkaloids and synthetic compounds. The effects of these substances depend on their respective substituent. Natural β-carbolines primarily influence brain functions but can also exhibit antioxidant effects. Synthetically designed β-carboline derivatives have recently been shown to have neuroprotective, cognitive enhancing and anti-cancer properties. Pharmacology The pharmacological effects of specific β-carbolines are dependent on their substituents. For example, the natural β-carboline harmine has substituents on position 7 and 1. Thereby, it acts as a selective inhibitor of the DYRK1A protein kinase, a molecule necessary for neurodevelopment. It also exhibits various antidepressant-like effects in rats by interacting with serotonin receptor 2A. Furthermore, it increases levels of the brain-derived neurotrophic factor (BDNF) in rat hippocampus. A decreased BDNF ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzothiophene
Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite tar. Benzothiophene has no household use. In addition to benzo hiophene, a second isomer is known: benzo hiophene. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP. It is also used in the manufacturing of dyes such as thioindigo. Synthesis Most syntheses of benzothiophene create substituted benzothiophenes as a precursor to further reactions. An example is the reaction of an alkyne-substituted 2-bromobenzene with either sodium sulphide or potassium sulphide to form benzothiophene with an alkyl substitution at position 2. Thiourea Thiourea () is an organosulfur c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
