Sulfur heterocycles

Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.

Sulfolane (also tetramethylene sulfone, systematic name: 1-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula . It is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene. Sulfolane is a polar aprotic solvent, and it is miscible with water.

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom. Some derivatives are of interest as drugs.

pharmaceutical drug

Thiane is a heterocyclic compound and an organosulfur compound with the formula (CH2)5S. It is a saturated six-membered ring with five carbon atoms and one sulfur atom. The compound is a colorless liquid. It can be prepared by the reaction of 1,5-dibromopentane with sodium sulfide:

Thiepane (also hexathiophane) is the organosulfur compound with the formula (CH2)6S. Thiepanes are seven-membered ring heterocycles that contains sulfide. The parent thiepane has seldom been studied.

Tazarotene, sold under the brand name Tazorac, among others, is a third-generation prescription topical retinoid. It is primarily used for the treatment of plaque psoriasis and acne. Tazarotene is also used as a therapeutic for photoaged and photodamaged skin. It is a member of the acetylenic class of retinoids.

chemical compound

Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom. It is more commonly encountered not on its own, but in anellated derivatives, several of which have been synthesized. Thietes are generally not very stable.

1,3,5-Trithiane is the chemical compound with the formula (CHS). This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.

6-APA ((+)-6-aminopenicillanic acid) is an organic compound that is used in the synthesis of β–lactam antibiotics including amoxicillin, ampicillin, oxacillin, and carbenicillin. The major commercial source of 6-APA is natural penicillin G, which contains an N-phenylacetyl substituent.

Lenthionine is an organosulfur compound with the formula . The compound consists of a 1,4- ring (pentathiepane). Lenthionine is a major component of the organosulfur compounds found in shiitake mushrooms (Lentinula edodes). onions, and garlic, and it is partly responsible for their flavor. The mechanism of its formation is unclear, but it likely involves the enzyme C–S lyase.

Thiirene is an organosulfur compound with the formula C2H2S. It can be viewed as a derivative of cyclopropene, but with the methylene group replaced by sulfur. It is antiaromatic and very labile.

Thiopyran is a heterocyclic compound with the chemical formula C5H6S. It has two isomers, 2H-thiopyran and 4H-thiopyran, which differ by the location of double bonds. Thiopyrans are analogous to pyrans in which the oxygen atoms have been replaced by sulfur atoms.

2,3-Dihydrothiophene is a heterocyclic compound and an organosulfur compound with the formula SC4H6. It is isomeric with the more symmetrical 2,5-dihydrothiophene. Both isomers of dihydrothiophene are colorless liquids with a thioether-like odor. In terms of their reactivity, both isomers exhibit characteristics of alkenes and thioethers, undergoing addition reactions at carbon and oxidation at sulfur. In contrast, thiophene engages in neither reaction.

Tetramethylenedisulfotetramine (TETS) is an organic compound used as a rodenticide (rat poison). It is an odorless, tasteless white powder that is slightly soluble in water, DMSO and acetone, and insoluble in methanol and ethanol. It is a sulfamide derivative. It can be synthesized by reacting sulfamide with formaldehyde solution in acidified water. When crystallized from acetone, it forms cubic crystals with a melting point of 255–260 °C.

Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus. It contains an unusual 1,2,3,4,5-benzopentathiepine ring system.

7-ACA (7-aminocephalosporanic acid) is the core chemical structure (a synthon) for the synthesis of cephalosporin antibiotics and intermediates. It can be obtained by chemoenzymatic hydrolysis of cephalosporin C.

Prulifloxacin is an older synthetic antibiotic of the fluoroquinolone class undergoing clinical trials prior to a possible NDA (New Drug Application) submission to the U.S. Food and Drug Administration (FDA). It is a prodrug which is metabolized in the body to the active compound ulifloxacin. It was developed over two decades ago by Nippon Shinyaku Co. and was patented in Japan in 1987 and in the United States in 1989.

Arsthinol (INN) is an organoarsenic compound with the formula . A antiprotozoal agent, it was first reported in 1949. It arises by the reaction of acetarsol with 2,3-dimercaptopropanol (British anti-Lewisite) and has been demonstrated to be effective against amoebiasis and yaws. It was marketed a few years later by Endo Products (Balarsen, Tablets, 0.1 g).

1,4,7-Trithiacyclononane, also called 9-ane-S3, is the thia-crown ether with the formula (CH2CH2S)3. This cyclic thioether is most often encountered as a tridentate ligand in coordination chemistry, where it forms transition metal thioether complexes.

1,4,2-Dithiazole is a heterocyclic compound consisting of an unsaturated five-membered ring containing two carbon atoms, one nitrogen atom, and two sulfur atoms. 1,4,2-Dithiazole compounds may be formed by the reaction of nitrile sulfide (formed by the thermolysis of oxathiazolone) with various reactive species; for instance thiocarbonyls via a 1,3-dipolar cycloaddition reaction. These compounds may be protonated by strong acids to give synthetically useful aromatic cations.

Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated; one (low-yielding) route is oxidation of a dithiolene complex. 3,4-Bis(trifluoromethyl)-1,2-dithiete is a particularly stable example.

Thiopyrylium is a cation with the chemical formula C5H5S+. It is analogous to the pyrylium cation with the oxygen atom replaced by a sulfur atom.

Lurbinectedin, sold under the brand name Zepzelca, is a medication used for the treatment of small cell lung cancer.

1,5-Dithiacyclooctane (DTCO) is an organosulfur compound with the formula (CHCH)CHS). This cyclic dithioether is a colorless oil that is soluble in polar solvents. It forms a variety of transition metal thioether complexes.

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula . Its covalent structure is , that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

Sulbentine (or dibenzthione) is an antifungal.

chemical compound

Suriclone (Suril) is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs. Other cyclopyrrolone drugs include zopiclone and pagoclone.

Quizartinib, sold under the brand name Vanflyta, is an anti-cancer medication used for the treatment of acute myeloid leukemia.

thumb|Benzylpenicillin, an example of a penam

Omapatrilat (INN, proposed trade name Vanlev) is an experimental antihypertensive agent that was never marketed. It inhibits both neprilysin (neutral endopeptidase, NEP) and angiotensin-converting enzyme (ACE). NEP inhibition results in elevated natriuretic peptide levels, promoting natriuresis, diuresis, vasodilation, and reductions in preload and ventricular remodeling.

Zosurabalpin (RG6006, Abx-MCP, Ro7223280) is an experimental antibiotic developed in a collaboration between the pharmaceutical company Roche and scientists from Harvard University, for the treatment of carbapenem-resistant Acinetobacter baumannii (CRAB). It targets a lipopolysaccharide transporter. It works by recognizing a composite binding site made up of both the Lpt transporter and its LPS substrate. The chemical family to which it belongs was first disclosed in 2019, but the particular structure of RG6006 remained confidential until publication of the testing results in 2023.

Suproclone is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs, developed by the French pharmaceutical company Rhône-Poulenc. Other cyclopyrrolone drugs include zopiclone, pagoclone and suriclone.

Trithiapentalene is an organic bicyclic molecule containing two sulfur heterocycles. Its 10-π aromatic structure is similar to naphthalene. There has been a literature dispute about whether the connectivity among the three sulfur atoms is a case of rapid tautomerization between two valence tautomers or a 3-center 4-electron bond. left|thumb|650x650px|Resonance (chemistry)|Resonance structures of trithiapentalene