ONE POT SYNTHESIS OF ARSONOLIPIDS<i>VIA</i>THIOARSENITE PRECURSORS

Serves, Spyros V.; Sotiropoulos, Demetrios N.; Ioannou, Panayiotis V.; Jain, Mahendra Kumar

doi:10.1080/10426509308034388

Cited by 48 publications

(18 citation statements)

References 18 publications

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“…Better yields were obtained by acylating the thioarsenite 4 (obtained by reduction of 3 with thiophenol), with fatty-acid chlorides/pyridine, followed by oxidation. 10 These arsonolipids proved to be of value in elucidating the mechanism of action of phospholipase A 2 11 and they are potent non-competitive inhibitors of carbonic anhydrase, isozyme II. 12 The arsonolipids form liposomes either alone 7,10 or in the presence of phospholipids and/or cholesterol (D. Fatouros et al, in preparation) and studies are under way to understand their properties.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of arsinolipids: non-isosteric analogues of phospholipids

Kordalis¹,

Ioannou²

2000

Appl. Organometal. Chem.

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Reaction of alkaline benzenearsonous and 2,3‐dihydroxypropylarsonous acids with rac‐glycidol affords the corresponding arsinic acids, which after reduction with thiophenol are acylated with either fatty‐acid chlorides/pyridine or fatty acids/dicyclohexylcarbodiimide/4‐dimethylaminopyridine and oxidized with hydrogen peroxide to give the arsinolipids (rac‐2,3‐diacyloxypropyl)phenylarsinic and bis‐(rac‐2,3‐diacyloxypropyl)arsinic acids. The latter is a non‐isosteric analogue of bisphosphatidic acid. Copyright © 2000 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Syntheses of arsinolipids: non-isosteric analogues of phospholipids

Kordalis¹,

Ioannou²

2000

Appl. Organometal. Chem.

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“…Since triphenylphosphine oxide was detected by TLC, then the 2-picolylarsenoso compound must have been formed and it was detected by 1 H-NMR [(ArCH 2 AsO) x : 3.46 ppm compared to (PhCH 2 AsO) x : 3.50 ppm 16 ]. 3,4 More recently, the RAs(SR ) 2 was exploited as a precursor of the nucleophile RAsO 2− 2 for the construction of more complex arsinolipids. Thus, the main route that has been followed was the attack of a nucleophile (most probably the Ph 3 P) on the α-carbon of the intermediate 16 with the expulsion of H 2 AsO − 3 which was isolated as As 2 O 3 .…”

Section: Resultsmentioning

confidence: 99%

“…The solid (244 mg) was (PhS) 3 As contaminated by PhSSPh (by TLC : petroleum ether, R f 0.12 and 0.40 respectively). More solid deposited afterward.…”

Section: With Thiophenolmentioning

confidence: 99%

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Preparation of 2-Picolylarsonic Acid and its Reductive Cleavage by Ascorbic Acid/Iodine and by Thiophenol

Ioannou

Afroudakis

Siskos

2002

Phosphorus, Sulfur, and Silicon and the Related Elements

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Contrary to dialkylaminoethyl halides, 2-picolyl chloride reacts with alkaline arsenite to give nearly quantitative yields 2-picolylarsonic acid. This acid is decomposed by ascorbic acid in the presence of catalytic amounts of iodine to 2-picoline and arsenious acid, most likely by hydride transfer from the ascorbic acid. Thiophenol decomposes this arsonic acid very quickly to 2-picoline, diphenyl disulfide and triphenyl trithioarsenite. In this case a proton from the thiophenol is transferred to the incipient 2-picolyl carbanion.

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“…in MeOH/conc. NH 3 (4:1)) 21,22 followed by spraying with 35% sulfuric acid and charring. Arsenic(III) oxide was detected, as 'AsO 3 3À ', by TLC and confirmed by IR spectroscopy (sharp peak at 802 cm À1 ).…”

Section: àmentioning

confidence: 99%