|
Nenitzescu Indole Synthesis
The Nenitzescu indole synthesis is a chemical reaction that forms 5-hydroxyindole derivatives from benzoquinone and β-aminocrotonic esters. This reaction was named for its discoverer, Costin Nenițescu, who first reported it in 1929. It can be performed with a number of different combinations of R-groups, which include methyl, methoxy, ethyl, propyl, and H substituents. There is also a solid-state variation in which the reaction takes place on a highly cross-linked polymer scaffold. The synthesis is particularly interesting because indoles are the foundation for a number of biochemically important molecules, including neurotransmitters and a new class of antitumor compounds. Mechanism The mechanism of a Nenitzescu reaction consists of a Michael addition, followed by a nucleophilic attack by the enamine pi bond, and then an elimination. The reaction was first published by Nenitzescu in 1929, and has since been refined by Allen ''et al.'' In his 1996 publication, Allen a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Costin Nenițescu
Costin D. Neniţescu in some scientific publication written as ''Nenitzescu'' (; 15 July 1902 – 28 July 1970) was a prominent Romanian chemist, and a professor at the Polytechnic University of Bucharest. He was a member of the Romanian Academy, a corresponding member of the German Academy of Sciences in Berlin, and a member of the Leopoldina Academy of Natural Scientists in Halle-Saale. Education and career After completing in 1920 his secondary studies at Gheorghe Lazăr High School, Neniţescu continued his studies at the Polytechnic Institute in Zürich and Ludwig Maximilian University in Munich, where he was one of the favorite students of Hans Fischer. He studied Friedel–Crafts-like reactions in the series of aliphatic hydrocarbons, the mechanism of the isomerization of cyclobasics, the halogen migration in cycles and chains, reactions induced by carbonium ions, and others. He identified a group of naphthenic acids in Romanian crude oil. He searched for ways of ob ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Solid-phase Synthesis
In chemistry, solid-phase synthesis is a method in which molecules are covalently bound on a solid support material and synthesised step-by-step in a single reaction vessel utilising selective protecting group chemistry. Benefits compared with normal synthesis in a liquid state include: * High efficiency and throughput * Increased simplicity and speed The reaction can be driven to completion and high yields through the use of excess reagent. In this method, building blocks are protected at all reactive functional groups. The order of functional group reactions can be controlled by the order of deprotection. This method is used for the synthesis of peptides, deoxyribonucleic acid ( DNA), ribonucleic acid ( RNA), and other molecules that need to be synthesised in a certain alignment. More recently, this method has also been used in combinatorial chemistry and other synthetic applications. The process was originally developed in the 1950s and 1960s by Robert Bruce Merrifield ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indole Forming Reactions
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 in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
COX-2 Inhibitor
COX-2 inhibitors are a type of nonsteroidal anti-inflammatory drug (NSAID) that directly targets cyclooxygenase-2, COX-2, an enzyme responsible for inflammation and pain. Targeting selectivity for COX-2 reduces the risk of peptic ulceration and is the main feature of celecoxib, rofecoxib, and other members of this drug class. After several COX-2-inhibiting drugs were approved for marketing, data from clinical trials revealed that COX-2 inhibitors caused a significant increase in heart attacks and strokes, with some drugs in the class having worse risks than others. Rofecoxib (sold under the brand name Vioxx) was taken off the market in 2004 because of these concerns, while celecoxib (sold under the brand name Celebrex) and traditional NSAIDs received boxed warnings on their labels. Many COX-2-specific inhibitors have been removed from the US market. As of December 2011, only Celebrex (generic name of celecoxib) is still available for purchase in the United States. In the European ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indometacin
Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins. It was patented in 1961 and approved for medical use in 1963. It is on the World Health Organization's List of Essential Medicines. In 2020, it was the 320th most commonly prescribed medication in the United States, with more than 800thousand prescriptions. Medical uses As an NSAID, indometacin is an analgesic, anti-inflammatory, and antipyretic. Clinical indications for indometacin include: Joint diseases *rheumatoid arthritis *ankylosing spondylitis *osteoarthritis * gouty arthritis *acute painful shoulder bursitis or tendinitis Headaches * Trigeminal autonomi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Serotonin
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vasoconstriction. Approximately 90% of the serotonin that the body produces is in the intestinal tract. Biochemically, the indoleamine molecule derives from the amino acid tryptophan, via the (rate-limiting) hydroxylation of the 5 position on the ring (forming the intermediate 5-hydroxytryptophan), and then decarboxylation to produce serotonin. Serotonin is primarily found in the enteric nervous system located in the gastrointestinal tract (GI tract). However, it is also produced in the central nervous system (CNS), specifically in the raphe nuclei located in the brainstem, Merkel cells located in the skin, pulmonary neuroendocrine cells and taste receptor cells in the tongue. Additionally, serotonin is stored in blood platelets a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrahedron (journal)
''Tetrahedron'' is a weekly peer-reviewed scientific journal covering the field of organic chemistry. According to the ''Journal Citation Reports'', ''Tetrahedron'' has a 2020 impact factor of 2.457. ''Tetrahedron'' and Elsevier, its publisher, support an annual symposium. In 2010, complaints were raised over its high subscription cost. Notable papers , the Web of Science lists ten papers from ''Tetrahedron'' that have more than 1000 citations. The four articles that have been cited more than 2000 times are: * – cited 2228 times * – cited 2162 times * – cited 2124 times * – cited 2107 times See also * '' Tetrahedron Letters'' * ''Tetrahedron Computer Methodology'' * ''Polyhedron In geometry, a polyhedron (plural polyhedra or polyhedrons; ) is a three-dimensional shape with flat polygonal faces, straight edges and sharp corners or vertices. A convex polyhedron is the convex hull of finitely many points, not all o ...'' (journal) Refer ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Madelung Synthesis
The Madelung synthesis is a chemical reaction that produces (substituted or unsubstituted) indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature. The Madelung synthesis was reported in 1912 by Walter Madelung, when he observed that 2-phenylindole was synthesized using N-benzoyl-o-toluidine and two equivalents of sodium ethoxide in a heated, airless, reaction. Common reaction conditions include use of sodium or potassium alkoxide as base in hexane or tetrahydrofuran solvents, at temperatures ranging between 200–400 °C. A hydrolysis step is also required in the synthesis. The Madelung synthesis is important because it is one of few known reactions that produce indoles from a base-catalyzed thermal cyclization of N-acyl-o-toluidines. The overall reaction for the Madelung synthesis follows. Overall reaction This method is essentially confined to the preparation of 2-alkinylindoles (not easily accessible through electrophilic aro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hemetsberger Indole Synthesis
The Hemetsberger indole synthesis (also called the Hemetsberger–Knittel synthesis) is a chemical reaction that thermally decomposes a 3-aryl-2-azido-propenoic ester into an indole-2-carboxylic ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides .... Yields are typically above 70%. However, this is not a popular reaction, due to the lack of stability and difficulty in synthesizing the starting material. Reaction mechanism The mechanism is unknown. However, azirine intermediates have been isolated. The mechanism is postulated to proceed via a nitrene intermediate. References {{reflist Indole forming reactions Name reactions ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fischer Indole Synthesis
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. The reaction was discovered in 1883 by Emil Fischer. Today antimigraine drugs of the triptan class are often synthesized by this method. This reaction can be catalyzed by Brønsted acids such as HCl, H2SO4, polyphosphoric acid and p-toluenesulfonic acid or Lewis acids such as boron trifluoride, zinc chloride, iron chloride, and aluminium chloride. Several reviews have been published. Reaction mechanism The reaction of a (substituted) phenyl hydrazine with a carbonyl (aldehyde or ketone) initially forms a phenylhydrazone which isomerizes to the respective enamine (or 'ene-hydrazine'). After protonation, a cyclic ,3sigmatropic rearrangement occurs producing an imine. The resulting imine forms a cyclic aminoacetal (or ''aminal''), which under acid catalysis eliminates NH3, resulting in t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polymer Architecture
Polymer architecture in polymer science relates to the way branching leads to a deviation from a strictly linear polymer chain. Branching may occur randomly or reactions may be designed so that specific architectures are targeted. It is an important microstructural feature. A polymer's architecture affects many of its physical properties including solution viscosity, melt viscosity, solubility in various solvents, glass transition temperature and the size of individual polymer coils in solution. Different polymer architectures Random branching Branches can form when the growing end of a polymer molecule reaches either (a) back around onto itself or (b) onto another polymer chain, both of which, via abstraction of a hydrogen, can create a mid-chain growth site. Branching can be quantified by the branching index. Cross linked polymer An effect related to branching is chemical crosslinking - the formation of covalent bonds between chains. Crosslinking tends to increase Tg and i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
