Varacin

Varacin

Names
IUPAC name 2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethanamine
Identifiers
CAS Number	134029-48-4
ChEMBL	ChEMBL151233
ChemSpider	156044
Jmol interactive 3D	Image
PubChem	179269
InChI 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 Key: HIKCOAGMCNIBMP-UHFFFAOYSA-N 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
SMILES NCCc2cc(OC)c(OC)c1SSSSSc12
Properties
Chemical formula	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 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.