Chemistry of polyfunctional molecules. Part 86. Organoarsenic compounds derived from 1,3-bis(di-iodoarsino)propane with monocyclic, tricyclic, and straight-chain structures; X-ray crystal structure of 2,8,13,14-tetraoxa-1,3,7,9-tetra-arsatricyclo[7.3.1.1]tetradecane

Ellermann, Jochen; Brehm, L.; Lindner, Ekkehard; Hiller, W.; Fawzi, Riad; Dickert, Franz L.; Waidhas, Manfred

doi:10.1039/dt9860000997

Cited by 14 publications

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“…The optical inactivity of arsenicin A and the absence of a Cotton effect are in line with these elements of symmetry. As-containing groups were also apparent from diagnostic [10] FTIR absorption bands at 674, 722 and 765 cm À1 . Our aim at a diffraction analysis was defeated by the difficulty of obtaining suitable crystals of either arsenicin A itself or a derivative from reactions of unequivocal mechanism.…”

Section: Resultsmentioning

confidence: 96%

On the First Polyarsenic Organic Compound from Nature: Arsenicin A from the New Caledonian Marine Sponge Echinochalina bargibanti

Mancini

Guella

Frostin

et al. 2006

Chemistry A European J

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Reported here is the first polyarsenic compound ever found in nature. Denominated arsenicin A, it was isolated along a bioassay-guided fractionation of the organic extract of the poecilosclerid sponge Echinochalina bargibanti collected from the north-eastern coast of New Caledonia. In defining an adamantine-type polyarsenic structure for this compound, deceptively simple NMR spectra were complemented by extensive mass spectral analysis. However, it was only the synthesis of a model compound that provided the basis to discriminate structure 4 from other spectrally compatible structures for arsenicin A; to this end, a comparative ab initio simulation of IR spectra for the natural and the synthetic compounds was decisive. Arsenicin A is endowed with potent bactericidal and fungicidal activities on human pathogenic strains. All this may revive pharmacological interest in arsenic compounds while prompting us to rethink the arsenic cycle in nature.

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Section: Resultsmentioning

confidence: 96%