Thiadiazine

Last updated
Thiadiazine
Thiadiazines.svg
Identifiers
3D model (JSmol)
PubChem CID
  • 1,2,4:InChI=1S/C3H4N2S/c1-2-6-5-3-4-1/h1-3H,(H,4,5)
    Key: YROIEQHEBPTQKR-UHFFFAOYSA-N
  • 4H-1,2,6:InChI=1S/C3H4N2S/c1-2-4-6-5-3-1/h2-3H,1H2
    Key: OMGHOYHDIXBBSI-UHFFFAOYSA-N
  • 1,3,4:InChI=1S/C3H4N2S/c1-2-6-3-5-4-1/h1-2H,3H2
    Key: KLVQAIJZDCCJRZ-UHFFFAOYSA-N
  • 1,2,4:C1=CSNC=N1
  • 4H-1,2,6:C1C=NSN=C1
  • 1,3,4:C1N=NC=CS1
Properties
C3H4N2S
Molar mass 100.14 g·mol−1
Related compounds
Related compounds
Thiadiazole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thiadiazine is a heterocyclic compound containing a six-membered ring composed of three carbon atoms, one sulfur atom, and two nitrogen atoms. [1] It exists in several isomeric forms, each characterized by the different arrangement of the sulfur and nitrogen atoms in the ring structure. [2] Common isomers include 1,2,4-thiadiazine, 1,2,6-thiadiazine, and 1,3,4-thiadiazine. [1] Thiadiazines have gained significant interest in organic and medicinal chemistry research due to their diverse potential biological activities, including antimicrobial, anti-inflammatory, and muscle relaxant properties. They have been explored their potential applications in treating conditions such as Huntington's disease, rheumatoid arthritis, and type 2 diabetes. [2] [1]

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<span class="mw-page-title-main">Xanthine oxidase</span> Class of enzymes

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<span class="mw-page-title-main">Metalloprotein</span> Protein that contains a metal ion cofactor

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<span class="mw-page-title-main">Imidazole</span> Chemical compound

Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.

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<span class="mw-page-title-main">Imidazothiazoles</span> Class of chemical compounds comprising a bicyclic heterocycle

Imidazothiazoles are a class of chemical compounds containing a bicyclic heterocycle consisting of an imidazole ring fused to a thiazole ring. The structure contains three non-carbon or heteroatoms: two nitrogen atoms and one sulfur atom. Imidazothiazole derivatives show a broad spectrum of in vitro, i.e. "in the petri dish", activity such as anticancer, antipsychotic, antimicrobial, antifungal, and anthelmintic.

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 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.

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References

  1. 1 2 3 Rodríguez H, Suárez M, Albericio F (June 2012). "Thiadiazines, N,N-heterocycles of biological relevance". Molecules (Basel, Switzerland). 17 (7): 7612–28. doi: 10.3390/molecules17077612 . PMC   6268759 . PMID   22732878.
  2. 1 2 Terrab L, Rosenker CJ, Johnstone L, Ngo LK, Zhang L, Ware NF, Miller B, Topacio AZ, Sannino S, Brodsky JL, Wipf P (May 2020). "Synthesis and Selective Functionalization of Thiadiazine 1,1-Dioxides with Efficacy in a Model of Huntington's Disease". ACS Medicinal Chemistry Letters. 11 (5): 984–990. doi:10.1021/acsmedchemlett.0c00018. PMC   7236266 . PMID   32435415.