Varacin

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Varacin
Skeletal formula of varacin
Ball-and-stick model of the varacin molecule
Names
IUPAC name
2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethanamine
Identifiers
3D model (Jmol)
ChemSpider
Properties
C10H13NO2S5
Molar mass 339.540 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

References[edit]

  1. ^ Makarieva, T. N.; Stonik, V. A.; Dmitrenok, A. S.; Grebnev, B. B.; Isakov, V. V.; Rebachyk, N. M.; Rashkes, Y. W. (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, E. M.; 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.