Benzothiazoles
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Benzothiazoles
Benzothiazole, or more specifically 1,3-benzothiazole, is an aromatic heterocyclic compound with the chemical formula . It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Firefly luciferin can be considered a derivative of benzothiazole. It has a sulfurous odor and meaty flavor. The three structural isomer, structural isomers of benzothizaole are 1,3-benzothiazole, 1,2-benzothiazole and 2,1-benzothiazole. Structure and reactivity Benzothiazoles consist of a 5-membered 1,3-thiazole ring Annulation, fused to a benzene ring. The nine atoms of the bicycle and the attached substituents are coplanar. The heterocyclic core of the molecule is readily substituted at the Methine group, methyne (CH) centre in the thiazole ring. Thiazole is electron-withdrawing. Synthesis and biosynthesis Benzothiazoles are typically prepared by treatment of 2-Aminothiophenol, 2-merc ...
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2-Aminobenzothiazole
2-Aminobenzothiazole is the organic compound with the formula . It is related to the parent benzothiazole, but with an amino group at the unique methyne position on the thiazole ring. As confirmed by X-ray crystallography, it is a planar molecule, which exists as the amine tautomer. 2-Aminobenzothiazoles are often prepared by cyclization of 2-bromo-substituted arylthioureas. : Isothiocyanic acid, which can be generated in situ from sodium thiocyanate, adds to anilines to also afford 2-aminobenzothiazoles. Many other methods are available. Diazotization of 2-aminobenzothiazoles gives diazonium salts. These salts undergo azo coupling with aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...s. In this way some are prepared some useful dyes such as Basic Blue 54. Referen ...
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2-mercaptobenzothiazole
2-Mercaptobenzothiazole is an organosulfur compound with the formula . A white solid, it is a reagent in organic synthesis and in the sulfur vulcanization of rubber. Structure The molecule is planar with a C=S double bond, so the name ''mercapto''benzothiazole is a misnomer, a more appropriate name could be benzothiazoline-2-thione. Solution measurements by NMR spectroscopy could not measure the presence of the thiol tautomer that the name implies, instead it exists as a thione/dithiocarbamate and the hydrogen appears on the nitrogen in the solid state, gas-phase, and in solution. Theory indicates that the thione tautomer is about 39 kJ/mol lower in energy than the thiol, and a hydrogen-bonded dimer of the thione has even lower energy. At alkaline pH greater than 7 the deprotonated thiolate form is most abundant. A protonated form could not be observed in the pH range 2-11. Synthesis The compound has been produced by many methods. The industrial route entails the high temperatur ...
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Firefly Luciferin
Firefly luciferin (also known as beetle luciferin) is the luciferin, precursor of the light-emitting compound, used for the firefly ( Lampyridae), railroad worm ( Phengodidae), starworm ( Rhagophthalmidae), and click-beetle ( Pyrophorini) bioluminescent systems. It is the substrate of firefly luciferase ( EC 1.13.12.7), which is responsible for the characteristic light emission of many firefly and other insect species in the visible spectra ranging from 530 until 630 nm. As with other luciferins, oxygen is essential for the luminescence mechanism, which involves the decomposition of a cyclic peroxide to produce excited-state molecules capable of emitting light as they relax to the ground state. Additionally, it has been found that adenosine triphosphate (ATP) and magnesium are required for light emission. History Much of the early work on the chemistry of the firefly luminescence was done in the lab of William D. McElroy at Johns Hopkins University. The luciferin was first is ...
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Riluzole
Riluzole is a medication used to treat amyotrophic lateral sclerosis (ALS) and other motor neuron diseases. Riluzole delays the onset of ventilator-dependence or tracheostomy in some people and may increase survival by two to three months. Riluzole is available in tablet and liquid form. Medical uses Amyotrophic lateral sclerosis Riluzole was approved in the United States for the treatment of ALS by the US Food and Drug Administration (FDA) in 1995. A Cochrane Library review states a 9% gain in the probability of surviving one year. Contraindications Contraindications for riluzole include: known prior hypersensitivity to riluzole or any of the excipients inside the preparations, liver disease, pregnancy or lactation. Adverse effects * Very common (>10% frequency): nausea; weakness; decreased lung function * Common (1–10% frequency): headache; dizziness; drowsiness; vomiting; abdominal pain; increased aminotransferases * Uncommon (0.1–1% frequency): pancreatitis; inter ...
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Thioflavin
Thioflavins are fluorescent dyes that are available as at least two compounds, namely Thioflavin T and Thioflavin S. Both are used for histology staining and biophysical studies of protein aggregation. In particular, these dyes have been used since 1989 to investigate amyloid formation. They are also used in biophysical studies of the electrophysiology of bacteria. Thioflavins are corrosive, irritant, and acutely toxic, causing serious eye damage. Thioflavin T has been used in research into Alzheimer's disease and other neurodegenerative diseases. Thioflavin T Thioflavin T (Basic Yellow 1, Methylene yellow, CI 49005, or ThT) is a benzothiazole salt obtained by the methylation of dehydrothiotoluidine with methanol in the presence of hydrochloric acid. The dye is widely used to visualize and quantify the presence of misfolded protein aggregates called amyloid, both ''in vitro'' and ''in vivo'' (e.g., plaques composed of amyloid beta found in the brains of Alzheimer's disease pat ...
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Dopamine Antagonists
A dopamine antagonist, also known as an anti-dopaminergic and a dopamine receptor antagonist (DRA), is a type of Pharmaceutical drug, drug which blocks dopamine receptors by receptor antagonism. Most antipsychotics are dopamine antagonists, and have been used in treating schizophrenia, bipolar disorder, and stimulant psychosis. Several other dopamine antagonists are antiemetics used in the treatment of nausea and vomiting. Receptor pharmacology Dopamine receptors are all G protein–coupled receptors, and are divided into two classes based on which G-protein they are coupled to. The D1-like class of dopamine receptors is coupled to Gαs/olf and stimulates Adenylyl cyclase, adenylate cyclase production, whereas the D2-like class is coupled to Gαi/o and thus inhibits adenylate cyclase production. D1-like receptors: D1 and D5 D1-like receptor, D1-like receptors – D1 and D5 are always found post-synaptically. The genes coding these receptors lack introns, so there are no splice ...
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Pramipexole
Pramipexole, sold under the brand Mirapex among others, is a medication used to treat Parkinson's disease and restless legs syndrome. In Parkinson's disease it may be used alone or together with levodopa. It is taken by mouth. Pramipexole is a dopamine agonist of the non-ergoline class. Pramipexole was approved for medical use in the United States in 1997 and was first manufactured by Pharmacia and Upjohn. It is available as a generic medication. In 2022, it was the 193rd most commonly prescribed medication in the United States, with more than 2million prescriptions. Medical uses Pramipexole is used in the treatment of Parkinson's disease and restless legs syndrome. Safety in pregnancy and breastfeeding is unknown. A 2008 meta-analysis found that pramipexole was more effective than ropinirole in the treatment of restless legs syndrome. It is occasionally prescribed off-label for depression. Its effectiveness as an antidepressant may be a product of its strong partial ag ...
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Monoamine Oxidase Inhibitors
Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especially for treatment-resistant depression and atypical depression. They are also used to treat panic disorder, social anxiety disorder, Parkinson's disease, and several other disorders. Reversible inhibitors of monoamine oxidase A (RIMAs) are a subclass of MAOIs that selectively and reversibly inhibit the MAO-A enzyme. RIMAs are used clinically in the treatment of depression and dysthymia. Due to their reversibility, they are safer in single-drug overdose than the older, irreversible MAOIs, and weaker in increasing the monoamines important in depressive disorder. RIMAs have not gained widespread market share in the United States. Medical uses MAOIs have been found to be effective in the treatment of panic disorder with agoraphob ...
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MAO-A
Monoamine oxidase A, also known as MAO-A, is an enzyme ( E.C. 1.4.3.4) that in humans is encoded by the ''MAOA'' gene. This gene is one of two neighboring gene family members that encode mitochondrial enzymes which catalyze the oxidative deamination of amines, such as norepinephrine, serotonin and tyramine. A mutation of this gene results in Brunner syndrome. This gene has also been associated with a variety of other psychiatric disorders, including antisocial behavior. Alternatively spliced transcript variants encoding multiple isoforms have been observed. Structures Gene Monoamine oxidase A, also known as MAO-A, is an enzyme that in humans is encoded by the ''MAOA'' gene. The promoter of ''MAOA'' contains conserved binding sites for Sp1, GATA2, and TBP. This gene is adjacent to a related gene ('' MAOB'') on the opposite strand of the X chromosome. In humans, there is a 30-base repeat sequence repeated several different numbers of times in the promoter region of ...
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Thiadiazole
In chemistry, thiadiazoles are a sub-family of azole compounds, with the name ''thiadiazole'' originating from the Hantzsch–Widman nomenclature. Structurally, they are five-membered heterocyclic compounds containing one sulfur and two nitrogen atoms. The ring is aromatic by virtue of the two double bonds and one of the lone pairs of electrons of sulfur. Four constitutional isomers are possible, differing by the relative positions of the sulfur and nitrogen atoms. The nomenclature thus includes the locations of each of those three atoms, with the first of the three numbers referring to the sulfur. The parent compounds are rarely synthesized and possess no particular application, however, compounds bearing them as a structural motif are fairly common in pharmacology. Of them, 1,3,4-thiadiazole is the most common, appearing in such medications as cephazolin and acetazolamide. 3,4-Dichloro-1,2,5-thiadiazole arises readily from cyanogen. In the Hurd–Mori reaction, an acyl hy ...
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