Synthesis of n-sulfamoyloxazolidinones and -perhydrooxazinones reactivity and use as donors in the transsulfamoylation reaction; application to the preparation of 2-chloroethylnitrososulfamides. IV

Dewynter, Georges; Abdaoui, Mohamed; Régaı̈nia, Zine; Montéro, Jean-Louis

doi:10.1016/0040-4020(96)00860-5

Cited by 34 publications

(18 citation statements)

References 16 publications

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“…The discussion of percentage contribution is based on the quantitative values, the sign of the coefficients in the corresponding equations, and the comparison of these coefficients among themselves. From these results, we conclude that the linear regression, according to Reichardt, and the multiple linear regression, according to Kamlet-Taft, both have a similar quality of fit, but the Kamlet-Taft solvatochromic parameters a, b and p* give more information and demonstrate that the solvent basicity is the least significant factor for the position of n abs , n ems and Δn (as revealed by the small estimates for b; see equations (8), (9) and (10) and their relatively large corresponding errors.…”

Section: Solvent Effectsmentioning

confidence: 77%

“…2-Chloroethylnitrososulfamids (CENSs) constitute a new family of oncostatic agents, structurally related to CENUs but devoid of any carbamoylating activity. Promising agents prepared on this basis have shown interesting cytotoxic activity and among them some proved to be considerably more potent than the parent nitrosourea (6)(7)(8)(9)(10)(11)(12).…”

Section: Introductionmentioning

confidence: 99%

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Solvent effects of N‐nitroso, N‐(2‐chloroethyl), N′,N′‐dibenzylsulfamid and its copper(II) and cobalt(II) complexes: fluorescence studies

et al. 2012

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The structure of N-nitroso, N-(2-chloroethyl), N',N'-dibenzylsulfamid (CENS) was established by X-ray crystallography. The atomic coordinates, factors of isotropic thermal agitation, bond lengths and valence angles were determined. The solvent effects on the electronic absorption and fluorescence spectra of CENS were investigated at room temperature. The effects of solvent polarity and of hydrogen bonding were interpreted by means of linear solvation energy relationships (LSERs). Multiple linear regression analysis indicated that the hydrogen donation properties of the solvent play an important role in determining the position of the absorption maximum, while the classical polarity of the medium is the only dominating parameter in determining the emission maximum and the Stokes' shift. Complexation of the investigated compound by two different transition metal ions was studied. Fluorescence measurements show that fluorescence quenching by cobalt(II) is more important than that by copper(II). This phenomenon can be attributed to good stereo-structural matching between the electronic configuration of the Co(2+) ion and the active site distribution of CENS in aqueous solution.

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Section: Solvent Effectsmentioning

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Solvent effects of N‐nitroso, N‐(2‐chloroethyl), N′,N′‐dibenzylsulfamid and its copper(II) and cobalt(II) complexes: fluorescence studies

et al. 2012

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“…The methods for the synthesis of oxazinanones include the displacement of a carbamate such as benzyloxylcarbamate [60] or aryloxylcarbamate [61] with a hydroxyl group to give 1,3-oxazinan-2-one derivatives. Several other methods include halogen mediated cyclization reactions [62][63][64], reactions that involve sulfonamide or sulfate intermediates [65][66], selenium mediated cyclization of aminoalcohol with carbon monoxide [67], intramolecular Michael additions [68], asymmetric dihydroxylation of homoallylic amines [69], and a Hoffmann rearrangement reaction [70].…”

Section: Oxazinanone Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Wang¹

2008

AIAMC

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Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi antibiotic resistant Gram-positive bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido methyl oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamate 5-hydroxymethyloxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one are also important building blocks for synthesizing other biologically active compounds. Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of Linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships will be reviewed.

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“…In reaction with nucleophiles, such as hydroxylamine hydrochloride and its O-benzyl and O-tert-butyl derivatives, 3 gave the Ncarboxylsulfamides 5-7 in 60-90% yields (Scheme 1, top). Starting from 2-chloroethylcarbamate 4, the 5-exo-tet heterocyclic closure was spontaneously carried out under the alkaline conditions of sulfamoylation [15] (the use of triethylamine in dichloromethane at 0ЊC), and the resulting compound 8 was obtained in 75% yield (Scheme 1, bottom).…”

Section: Chemistrymentioning

confidence: 99%

N-hydroxysulfamides as analog ofN-hydroxyurea: synthesis and biological evaluation

et al. 2001

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Synthesis of n-sulfamoyloxazolidinones and -perhydrooxazinones reactivity and use as donors in the transsulfamoylation reaction; application to the preparation of 2-chloroethylnitrososulfamides. IV

Cited by 34 publications

References 16 publications

Solvent effects of N‐nitroso, N‐(2‐chloroethyl), N′,N′‐dibenzylsulfamid and its copper(II) and cobalt(II) complexes: fluorescence studies

Solvent effects of N‐nitroso, N‐(2‐chloroethyl), N′,N′‐dibenzylsulfamid and its copper(II) and cobalt(II) complexes: fluorescence studies

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

N-hydroxysulfamides as analog ofN-hydroxyurea: synthesis and biological evaluation

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