Crystal and molecule structure of 1,3,5,7-tetraarsa-2,4,6,8-tetraoxaadamantane

Kopf, Jürgen; Deuten, K. Von; Klar, G.

doi:10.1016/s0020-1693(00)91936-4

Cited by 22 publications

(11 citation statements)

References 7 publications

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“…2,4,6,8-Tetraoxa-1,3,5,7-tetraarsa-adamantane ( 3 ) 15 , the analogue of molecular composition C 2 H 4 As 4 O 4 , was expected from the MW-assisted reaction of arsenic (III) oxide with K 2 CO 3 , acetic acid and acetic anhydride (1:1:4:8 molar equivalent, respectively) under optimized conditions (138 °C for 0.5 h, followed by hydrolysis at 80 °C for 0.5 h). The atmospheric pressure chemical ionization (APCI)-MS spectrum in positive ion mode of the crude reaction mixture, revealed a signal at m/z 392.7 attributable to compound 3 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Mancini

Planchestainer

Defant

2017

Sci Rep

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In the light of the promising bioactivity of the tetraarsenic marine metabolite arsenicin A, the dimethyl analogue 2 and four isomeric methylene homologues (including the natural product itself) were obtained using a one-pot microwave-assisted synthesis, starting from arsenic (III) oxide. Due to the poor diagnostic value of the NMR technique in the structural elucidation of these molecules, they were fully characterized by mass spectrometry and infrared (IR)-spectroscopy, comparing density functional theory (DFT) simulated and experimental spectra. This synthetic procedure provided a fast and efficient access to the cytotoxicity evaluation of organoarsenical leads of the natural hit molecule. From in vitro screening, each tested compound resulted in being more active than the FDA-approved arsenic trioxide, with the most lipophilic molecule in the series showing the best growth inhibition of both leukemia and solid tumor cell lines. These results may open promising perspectives in the development of new more potent and selective arsenical drugs against solid tumors.

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Section: Resultsmentioning

confidence: 99%

Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Mancini

Planchestainer

Defant

2017

Sci Rep

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“…The structure of one of the independent molecules of (S As ,S As ,S As ,S As )-1 is shown in Figure 2 7), C-As-O=99.3(10). 8 The novel adamantane-type structure of Arsenicin A poses challenging questions about its biosynthesis and relationship to the variety of known marine organoarsenicals. 9 It is hoped that the synthesis presented here will facilitate further chemical and biological work on this unusual natural product.…”

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Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure

et al. 2009

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“…These reactions usually led to a variety of metallacyclic products containing sulfur and phosphorus or arsenic within the ring. Even though the metal-mediated breaking of As-S bonds in inorganic molecules such as As 4 S 4 has received considerable attention [54][55][56][57][58][59][60][61][62], the cleavage of As-S bonds in thioarsines remains relatively unexplored. Compared to the rich coordination chemistry of PPh 2 (SPh), only a few reactions of AsPh 2 (SPh) with some metal carbonyl complexes are reported.…”

Section: Coordination Chemistry Of Eph 2 (Sph)mentioning

confidence: 99%

Synthesis and coordination chemistry of thiophenol-based heterodonor ligands containing P,S, As,S and P,SAs donor atoms

Sárosi

Silaghi‐Dumitrescu

Hey‐Hawkins

2013

Maced. J. Chem. Chem. Eng.

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This review article describes the synthesis and coordination chemistry of three types of thiophenol-based heterodonor ligands containing tertiary phosphine and/or arsine groups in combination with sulfur. Phenylthio(diphenyl)phosphine and -arsine ligands, EPh2(SPh) (E = P, As), incorporate an E–S bond in their structures. Upon reaction with different metal carbonyls, metal-mediated cleavage of the E–S bonds of these ligands has been observed, leading to a variety of sulfur- and phosphorus- or arsenic-containing metallacycles. The structurally isomeric phosphino- and arsinoarylthiols HSC6H4-2-EPh2 (ESH) combine a phosphine or arsine centre with a thiol functionality, which is usually deprotonated on coordination. These compounds have been shown to be very versatile ligands that form stable complexes with a wide range of transition metals. The heterotopic ligand 1-Ph2AsSC6H4-2-PPh2 (P,SAs) not only combines the properties of phenylthio(diphenyl)arsine and 2-diphenylphosphanylbenzenethiol by incorporating all three donor atoms in its structure, but also allows the effect of the PPh2 group in the ortho position on the cleavage of the As–S bond to be studied.

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Crystal and molecule structure of 1,3,5,7-tetraarsa-2,4,6,8-tetraoxaadamantane

Cited by 22 publications

References 7 publications

Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Arsenicin A, A Natural Polyarsenical: Synthesis and Crystal Structure

Synthesis and coordination chemistry of thiophenol-based heterodonor ligands containing P,S, As,S and P,SAs donor atoms

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