Varacin

Varacin
Skeletal formula of varacin
Varacin skeletal structure
Ball-and-stick model of the varacin molecule
Names
Preferred IUPAC name
2-(8,9-Dimethoxy-1,2,3,4,5-benzopentathiepin-6-yl)ethan-1-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3 X markN
    Key: HIKCOAGMCNIBMP-UHFFFAOYSA-N X markN
  • InChI=1/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3
    Key: HIKCOAGMCNIBMP-UHFFFAOYAP
  • NCCc2cc(OC)c(OC)c1SSSSSc12
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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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.

Bioactivity

The compound reacts with DNA. Synthetic analogues have been investigated for their antimicrobial and antitumour properties. Because of its potent biological activity and unusual and challenging ring system, it has been a popular target of efforts toward its total synthesis.

Varacin and a few related polysulfur natural products potentially exhibit planar chirality.

References

  1. ↑ Makarieva TN, Stonik VA, Dmitrenok AS, Grebnev BB, Isakov VV, Rebachyk NM, Rashkes YW (February 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 (October 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 (January 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.
  4. ↑ Behar V, Danishefsky SJ (1993-07-01). "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society. 115 (15): 7017–7018. doi:10.1021/ja00068a087. ISSN 0002-7863.
  5. ↑ Ford PW, Narbut MR, Belli J, Davidson BS (1994-10-01). "Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A". The Journal of Organic Chemistry. 59 (20): 5955–5960. doi:10.1021/jo00099a026. ISSN 0022-3263.
  6. ↑ Toste FD, Still IW (1995-07-01). "A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin". Journal of the American Chemical Society. 117 (27): 7261–7262. doi:10.1021/ja00132a033.
  7. ↑ Brzostowska, Edyta M.; Paulynice, Martine; Bentley, Ronald; Greer, Alexander (2007-07-01). "Planar Chirality due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity". Chemical Research in Toxicology. 20 (7): 1046–1052. doi:10.1021/tx7000465. ISSN 0893-228X.