Varacin - Wikiwand

Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus.^[1] It contains an unusual 1,2,3,4,5-benzopentathiepine ring system.

Quick facts Names, Identifiers ...

Varacin
Names
Varacin skeletal structure

Preferred IUPAC name 2-(8,9-Dimethoxy-1,2,3,4,5-benzopentathiepin-6-yl)ethan-1-amine
Identifiers
CAS Number	134029-48-4^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL151233^N
ChemSpider	156044^N
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^N Key: HIKCOAGMCNIBMP-UHFFFAOYSA-N^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). N verify (what is ^YN ?) Infobox references

Bioactivity

The compound reacts with DNA. 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]

Varacin and a few related polysulfur natural products potentially exhibit planar chirality.^[7]

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.

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