Thiazoles
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Thiazoles
Thiazole (), or 1,3-thiazole, is a 5-membered heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS. The thiazole ring is notable as a component of the vitamin thiamine (B1). Molecular and electronic structure Thiazoles are members of the azoles, heterocycles that include imidazoles and oxazoles. Thiazole can also be considered a functional group when part of a larger molecule. Being planar thiazoles are characterized by significant pi-electron delocalization and have some degree of aromaticity, more so than the corresponding oxazoles. This aromaticity is evidenced by the 1H NMR chemical shift of the ring protons, which absorb between 7.27 and 8.77 ppm, indicating a strong diamagnetic ring current. The calculated pi-electron density marks C5 as the primary site for electrophilic substitution, and C2-H a ...
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Thiamine
Thiamine, also known as thiamin and vitamin B1, is a vitamin – an Nutrient#Micronutrients, essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some Metabolism, metabolic reactions, including the breakdown of Carbohydrate metabolism, glucose and amino acids. Food sources of thiamine include whole grains, legumes, and some meats and fish. Refined grain, Grain processing removes much of the vitamin content, so in many countries cereals and flours are food fortification, enriched with thiamine. Supplements and medications are available to treat and prevent thiamine deficiency and the disorders that result from it such as Thiamine deficiency#Dry beriberi, beriberi and Wernicke encephalopathy. They are also used to treat maple syrup urine disease and Leigh syndrome. Supplements and medications are typically taken Route of administration#Oral ...
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Meloxicam
Meloxicam, sold under the brand name Mobic among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation in rheumatic diseases and osteoarthritis. It is taken by mouth or given by injection into a vein. It is recommended that it be used for as short a period as possible and at a low dose. Common side effects include abdominal pain, dizziness, swelling, headache, and a rash. Serious side effects may include heart disease, stroke, kidney problems, and stomach ulcers. Use is not recommended in the third trimester of pregnancy. It blocks cyclooxygenase-2 (COX-2) more than it blocks cyclooxygenase-1 (COX-1). It is in the oxicam family of chemicals and is closely related to piroxicam. Meloxicam was patented in 1977 and approved for medical use in the United States in 2000. It was developed by Boehringer Ingelheim and is available as a generic medication. In 2022, it was the 29th most commonly prescribed medication in the United States, w ...
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Epothilone
Epothilones are a class of potential cancer drugs. Like taxanes, they prevent cancer cells from dividing by interfering with tubulin, but in early trials, epothilones have better efficacy and milder adverse effects than taxanes. Epothilones were originally identified as metabolites produced by the soil-dwelling myxobacterium ''Sorangium cellulosum''. , epothilones A to F have been identified and characterized. Early studies in cancer cell lines and human cancer patients indicate superior efficacy to the taxanes. Their mechanism of action is similar, but their chemical structure is simpler. Due to their better water solubility, cremophors (solubilizing agents used for paclitaxel which can affect cardiac function and cause severe hypersensitivity) are not needed. Endotoxin-like properties known from paclitaxel, like activation of macrophages synthesizing inflammatory cytokines and nitric oxide, are not observed for epothilone B. History The structure of epothilone A was determin ...
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Thiabendazole
Tiabendazole (International Nonproprietary Name, INN, British Approved Name, BAN), also known as thiabendazole (Australian Approved Name, AAN, United States Adopted Name, USAN) or TBZ and the trade names Mintezol, Tresaderm, and Arbotect, is a preservative, an antifungal agent, and an antiparasitic agent. Uses Preservative Tiabendazole is used primarily to control Mold (fungus), mold, blight, and other fungal diseases in fruits (e.g. Orange (fruit), oranges) and vegetables; it is also used as a prophylaxis, prophylactic treatment for Dutch elm disease. Tiabendazole is also used as a food additive, a preservative with E number E233 (INS number 233). For example, it is applied to bananas to ensure freshness, and is a common ingredient in the waxes applied to the skins of citrus fruits. It is not approved as a food additive in the EU, Australia and New Zealand. Use in treatment of aspergillosis has been reported. It is also used in anti-fungal wallboards as a mixture with a ...
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Heterocyclic Compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of py ...
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Fungicide
Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, including humans. Fungicides are also used to control oomycetes, which are not taxonomically/genetically fungi, although sharing similar methods of infecting plants. Fungicides can either be contact, translaminar or systemic. Contact fungicides are not taken up into the plant tissue and protect only the plant where the spray is deposited. Translaminar fungicides redistribute the fungicide from the upper, sprayed leaf surface to the lower, unsprayed surface. Systemic fungicides are taken up and redistributed through the xylem vessels. Few fungicides move to all parts of a plant. Some are locally systemic, and some move upward. Most fungicides that can be bought retail are sold in liquid form, the active ingredient being present at 0.08% i ...
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Herz Reaction
The Herz reaction, named after the chemist Richard Herz, is the chemical conversion of an aniline to the benzo dithiazolium salt by its reaction with disulfur dichloride. The salt is called a Herz salt. Hydrolysis of this Herz salt give the corresponding sodium thiolate, which can be further converted to the 2-aminothiophenol. The 2-aminothiophenols are suitable for diazotization, giving benzothiadiazoles.{{cite journal , doi=10.1039/J39700002250 , title=1,2,3-Benzothiadiazoles. Part I. A simplified synthesis of 1,2,3-benzothiadiazoles , year=1970 , last1=Kirby , first1=P. , last2=Soloway , first2=S. B. , last3=Davies , first3=J. H. , last4=Webb , first4=Shirley B. , journal=Journal of the Chemical Society C: Organic , issue=16 , page=2250 Instead the sodium 2-aminothiophenolate can be converted to a 1,3-benzothiazole. : Dyes Aniline 5 is converted to compound 6, in three steps; # conversion to an ortho- aminothiol through the Herz-reaction (aniline 5 and disulfur dichlori ...
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Carbon Disulfide
Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as a building block in organic synthesis. Pure carbon disulfide has a pleasant, ether- or chloroform-like odor, but commercial samples are usually yellowish and are typically contaminated with foul-smelling impurities.. History In 1796, the German chemist Wilhelm August Lampadius (1772–1842) first prepared carbon disulfide by heating pyrite with moist charcoal. He called it "liquid sulfur" (''flüssig Schwefel''). The composition of carbon disulfide was finally determined in 1813 by the team of the Swedish chemist Jöns Jacob Berzelius (1779–1848) and the Swiss-British chemist Alexander Marcet (1770–1822). Their analysis was consistent with an empirical formula of CS2. Occurrence, manufacture, properties Small amounts of carbon ...
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Chloroacetone
Chloroacetone is a chemical compound with the chemical formula, formula . At Standard temperature and pressure, STP it is a colorless liquid with a pungent odor. On exposure to light, it turns to a dark yellow-amber color. It was used as a lachrymatory agent, tear gas in World War I. Synthesis Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone. Applications Chloroacetone is used to make dye couplers for colour photography, and is an intermediate in chemical manufacturing. It is also used in the Feist-Benary synthesis of furans. : *Reaction of phenoxide with chloroacetone gives phenoxyacetone, which is used to make a wide variety of different pharmaceuticals. A catalytic amount of potassium iodide is also necessary to facilitate a Finkelstein reaction. Purification Chloroacetone purchased from commercial suppliers contains 5% impurities including mesityl oxide, which is not removed by distillation. Mesityl oxide ...
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Thioacetamide
Thioacetamide is an organosulfur compound with the formula C2 H5 N S. This white crystalline solid is soluble in water and serves as a source of sulfide ions in the synthesis of organic and inorganic compounds. It is a prototypical thioamide. Research Thioacetamide is known to induce acute or chronic liver disease (fibrosis and cirrhosis) in the experimental animal model. Its administration in rat induces hepatic encephalopathy, metabolic acidosis, increased levels of transaminases, abnormal coagulation, and centrilobular necrosis, which are the main features of the clinical chronic liver disease so thioacetamide can precisely replicate the initiation and progression of human liver disease in an experimental animal model. Coordination chemistry Thioacetamide is widely used in classical qualitative inorganic analysis as an in situ source for sulfide ions. Thus, treatment of aqueous solutions of many metal cations to a solution of thioacetamide affords the corresponding metal s ...
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Thioamide
A thioamide (rarely, thionamide, but also known as thiourylenes) is a functional group with the general structure , where are any groups (typically organyl groups or hydrogen). Analogous to amides, thioamides exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier. Synthesis Thioamides are typically prepared by treating amides with phosphorus sulfides such as phosphorus pentasulfide, a reaction first described in the 1870s. An alternative to P2S5 is its more soluble analogue Lawesson's reagent. The Willgerodt-Kindler reaction can give benzylthioamides via an analogous process. These transformations can be seen in the synthesis of tolrestat. : The reaction of nitriles with hydrogen sulfide also affords thioamides: : Imidoyl chlorides react with hydrogen sulfide to produce thioamides. : Reactions A well-known thioamide is thioacetamide, which is used as a source of the sulfide ion. Thioamides are precursors to heterocycles. Such ap ...
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