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;
	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 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]

References

↑ "Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp". Journal of Natural Products 58 (2): 254–8. February 1995. doi:10.1021/np50116a015. PMID 7769392.
↑ "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. October 2001. doi:10.1021/ja016495p. PMID 11603989.
↑ "The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents". Journal of the American Chemical Society 125 (2): 396–404. January 2003. doi:10.1021/ja027416s. PMID 12517151.
↑ "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society 115 (15): 7017–7018. 1993-07-01. doi:10.1021/ja00068a087. ISSN 0002-7863.
↑ "Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A". The Journal of Organic Chemistry 59 (20): 5955–5960. 1994-10-01. doi:10.1021/jo00099a026. ISSN 0022-3263.
↑ "A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin". Journal of the American Chemical Society 117 (27): 7261–7262. 1995-07-01. doi:10.1021/ja00132a033.

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[1] "Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp". Journal of Natural Products 58 (2): 254–8. February 1995. doi:10.1021/np50116a015. PMID 7769392.

[2] "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. October 2001. doi:10.1021/ja016495p. PMID 11603989.

[3] "The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents". Journal of the American Chemical Society 125 (2): 396–404. January 2003. doi:10.1021/ja027416s. PMID 12517151.

[4] "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society 115 (15): 7017–7018. 1993-07-01. doi:10.1021/ja00068a087. ISSN 0002-7863.

[5] "Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A". The Journal of Organic Chemistry 59 (20): 5955–5960. 1994-10-01. doi:10.1021/jo00099a026. ISSN 0022-3263.

[6] "A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin". Journal of the American Chemical Society 117 (27): 7261–7262. 1995-07-01. doi:10.1021/ja00132a033.

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Varacin

Topic: Chemistry

References