Varacin

Varacin
IUPAC name

2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethanamine
Identifiers
CAS number 134029-48-4 Y
PubChem 179269
ChEMBL CHEMBL151233 N
Jmol-3D images Image 1
Properties
Molecular formula C10H13NO2S5
Molar mass 339.540 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Varacin is a bicyclic organosulfur compound originally found in marine ascidiacea from the Polycitor family.[1] It contains an unusual pentathiepin ring which reacts with DNA, and varacin and synthetic analogues have been investigated for their antimicrobial and anti-tumour properties.[2][3]

References

  1. ^ Makarieva, TN; Stonik, VA; Dmitrenok, AS; Grebnev, BB; Isakov, VV; Rebachyk, NM; Rashkes, YW (1995). "Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp". Journal of natural products 58 (2): 254–8. doi:10.1021/np50116a015. PMID 7769392. 
  2. ^ Greer, A (2001). "On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate". Journal of the American Chemical Society 123 (42): 10379–86. doi:10.1021/ja016495p. PMID 11603989. 
  3. ^ Brzostowska, EM; Greer, A (2003). "The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents". Journal of the American Chemical Society 125 (2): 396–404. doi:10.1021/ja027416s. PMID 12517151.