Varacin

Varacin
Names
	Preferred IUPAC name 2-(8,9-Dimethoxy-1,2,3,4,5-benzopentathiepin-6-yl)ethan-1-amine
Identifiers
CAS Number	134029-48-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL151233 ;
ChemSpider	156044 ;
PubChem CID	179269;
CompTox Dashboard (EPA)	DTXSID10158465 ;
	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). verify (what is ?) 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] Because of its potent biological activity and unusual and challenging ring system, it has been a popular target of efforts toward its total synthesis.^[4]^[5]^[6]

By virtue of the unsymmetrically substituted benzopentathiepin ring system, varacin and a few related polysulfane natural products exist as potentially isolable enantiomers as a result of planar chirality.^[7]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]