ChemInform Abstract: Design, Synthesis and Biological Study of New Antiparasitic Spiroarsoranes.

Loiseau, Philippe M.; Rekik, L.; Madaule, Yves; Gayral, Philippe; Wolf, J. G.

doi:10.1002/chin.199351232

Cited by 1 publication

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast to the common handling procedures, the Loiseau group exposed arylarsoranes to physiological media and found considerable life spans, though these substances rapidly hydrolyze at higher pH values. 24,25 The former finding is somewhat in contrast to claims from other authors. 18,26 In this work we report on attempts to develop a carbohydrate-based arsorane chemistry.…”

Section: Introductionmentioning

confidence: 69%

“…Hence, most researchers avoid contact of arsoranes with water, which would be a serious restriction for the use of hydrophilic carbohydrate-derived substituents. In contrast to the common handling procedures, the Loiseau group exposed arylarsoranes to physiological media and found considerable life spans, though these substances rapidly hydrolyze at higher pH values. , The former finding is somewhat in contrast to claims from other authors. , …”

Section: Introductionmentioning

confidence: 96%

See 1 more Smart Citation

From Simple Diols to Carbohydrate Derivatives of Phenylarsonic Acid

Betz

Klüfers

2008

Inorg. Chem.

View full text Add to dashboard Cite

A series of spiro-arsoranes bearing a phenyl moiety as the fifth substituent were synthesized applying open-chain, as well as cyclic vicinal diols, as chelating molecules by condensation reactions in aprotic solvents. The products synthesized are the spiro compounds of the general formula PhAs(DiolH(-2))(2) derived from the vicinal diols meso-2,3-butanediol, PhAs(meso-2,3-ButdH(-2))(2) (1), exo-cis-2,3-norbornanediol, PhAs{exo-cis-NobdH(-2)}(2) (2), cis-1,2-cyclopentanediol, PhAs(cis-1,2-CptdH(-2))(2) (3), anhydroerythritol, PhAs(AnErytH(-2))(2) (4), cis-1,2-cyclohexanediol, PhAs(cis-1,2-ChxdH(-2))(2) (5), and rac-trans-1,2-cyclohexanediol, rac-{PhAs(trans-1,2-ChxdH(-2))(2)} (6) which were identified as mononuclear compounds. A novel dimeric double-spiro environment for oxyarsoranes was found in the reaction products derived from the sterically demanding diols 1,1'-bicyclohexyl-1,1'-diol {PhAs(BhxdH(-2))O}(2) (7) and perfluorpinacol, {PhAs(FpinH(-2))O}(2) (8). The stability of the compounds in acidic and neutral aqueous media in the presence of organic co-solvents was investigated. A convenient synthetic procedure for spiro-oxyarsoranes, applying water as the solvent, was developed and proven to be advantageous. All of the compounds synthesized in this study were characterized by means of melting-point measurement, single-crystal X-ray analysis, NMR, IR, Raman, UV/vis, and mass spectrometry. The principles found for these reactions were valid for the methyl glycosides of beta-D-ribofuranose and alpha-D-mannopyranose. The spiro-arsorane derived from methyl alpha-D-mannopyranoside, PhAs(Me-alpha-D-Manp2,3H(-2))(2) (9), is the first example of a structurally characterized carbohydrate-arsenic(V) compound.

show abstract

Section: Introductionmentioning

confidence: 69%