Tawfik Gharbaoui's research while affiliated with French National Centre for Scientific Research and other places
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Publications (22)
Base-promoted fragmentation of products resulting from srn1 reactions between gem halonitro alkanes and cyclanone β-esters as nucleophiles gives rise to di- or trifunctionalized olefins. These olefins carry a chain whose length is determined by the size of the ring in the cyclic nucleophile.
vic-Dinitro compounds containing a nitrodioxane subunit can be obtained by SRN1 reactions between either open chain gem-chloronitro derivatives as substrates and an anion from nitrodioxane as the nucleophile or 'reversed' reagents namely gem-chloronitrodioxane (substrate) and anions from nitro derivatives. The former access is more efficient and is...
Two strategies have been developed to synthesize both enantiomers of piperidin-2-yl-phosphonic acid. The first one uses the double condensation of glutaraldehyde with (R)-(−)-phenylglycinol and triethylphosphite to give 2-ethylphosphonate-6-oxazolopiperidine 2 which furnished in few steps (S)-(+)-piperidin-2yl-phosphonic acid (5) in 58% ee. The sec...
A simple and general asymmetric synthesis of alpha-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-alpha-substituted amino phosphonic acids in good over...
N-Azolyl olefins undergo a cohalogenation reaction when treated by the NBS/ROH system to give novel N-(bromoalkoxypropane) azolyl derivatives.
Carbocyclic oxetanocin analogues containing 3-fluoro or 3-hydroxy cyclobutyl moieties and different natural bases, have been prepared from the olefinic precursors either by direct fluoro-iodination (AgF-I2) or by DAST fluorination of the bromhydrin. The latter allowed the synthesis of the corresponding phosphonate derivatives as well.
vic-Dinitro compounds containing a nitrodioxane subunit can be obtained by SRN1 reactions between either open chain gem-chloronitro derivatives as substrates and an anion from nitrodioxane as the nucleophile or ‘reversed’ reagents namely gem-chloronitrodioxane (substrate) and anions from nitro derivatives. The former access is more efficient and is...
The oxidation of 9-vinyladenine derivatives (1a-c) with m-chloroperoxybenzoic acid (MCPBA) leads selectively to the corresponding N-1 oxides (2a-c) and when the 6-amino group is protected, the oxidation occurs on the double bond of the olefinic chain to give the epoxides (6a, b) selectively.
The synthesis of new N-azolyl (N9-adenine; 4-nitroimidazole) tetrasubstituted and functionalized olefins is based upon Grob type fragmentation or E RC 1 elimination reactions carried out on products obtained by two sequential S RN 1 reactions. © 1994 Georg Thieme Verlag, Rudigerstr. 14, 70469 Stuttgart, Germany. All rights reserved.
Under photostimulated SgNl conditions the cytosine nitranion behaves as a nucleophile toward the carbon radical generated from gem halonitro, or gem dinitroalcane derivatives to give regiospecifically the N-1 alkyled cytosine compound which is representative of a new series of cytosine acyclonucleosides. Uracile and its 5-fluoro or 5-nitro analogs...
6-Chloropurine and 2-amino-6-chloropurine were discovered to be efficient nucleophiles in SRN1 reactions with various gem halonitroalkane derivatives as substrates to give high yield of N-9 alkylated purine derivatives in a N-9/N-7 ratio greater than 95/5
Phenylselenenyl bromide permits the efficient synthesis, in two steps, under mild conditions and in good yield of the allylic bromide 8 from 6-chloro-9-(3-methylidene-1-cyclobutyl) purine 4. Depending on the temperature, 9-[(1-hydroxymethyl)-cyclobut-1-ene-3-yl] adenine 1 and 1-(adenin-9-yl)-3-methylidene-but-1-ene-4-ol 2 were then specifically obt...
Two series of new nucleoside derivatives, acyclic nucleosides and tricyclic base nucleosides, were screened for cellular toxicity and against HIV-1. Compounds were tested on MT4, MT2, U937 cell lines and PBMCs in multiwell tissue culture plates. Cells were infected in vitro with 2 TCID50/105 cells or 0.2 TCID50/105 cells of HIV-1-LAV-1. Two out of...
Citations
... Three different laboratory strains of viruses were used in the present study which are the following, herpes simplex virus type 1 (HSV-1-KOS), varicella-Zoster virus (VZV) and human cytomegalo virus (HCMV) to evaluate antiviral potential of the synthesized molecules. The reason for selecting HSV strain KOS is because it has been widely used in many research studies to study HSV-1 replication, gene expression, and pathogenesis (Clayette et al., 1991 andKodama et al., 2001;Montagu et al., 2011). Moreover, the HSV-1 KOS strain has been known to be less virulent, less pathogenic, and has better ability to attach to the host cells compared to other HSV strains and can also produce bigger plaques and can better associate to host cells via attachment, which means virus particles that endure attachment to or within the host cell once replicated. ...
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... NMR spectra were recorded on a Varian instrument (400 MHz for 1 H; Varian, Inc., Palo Alto, CA) or a Mercury instrument (200 MHz for 1 H) and calibrated using tetramethylsilane, P(O)Ph 3 , and the residual solvent signal as internal standards; chemical shifts (δ) are expressed in parts per million (ppm) and coupling constants (J) in Hertz, and an asterisk (*) indicates a duplicate signal corresponding to the minor rotamer. High-resolution FAB + and CI + mass spectra [high-resolution mass spectrometry (HRMS)] were obtained on a JEOL MStation MS-700. 1 H and 13 C NMR data for the compounds 13-15 [46,52,53] and 5 [54] were identical to those described in the literature. ...
... i R 2 +R 2 = -(CH 2 ) 3 -; -(CH 2 ) 4 -; -(CH 2 ) 5 -X = lone pair; Se A B Figure. N-phosphorylated diaminocarbenes and C-phosphorylated formamidines insertion of a phosphorus atom into the C-O linkage of oxazolidine that is a key step in the synthesis of α-amino phosphonic acids [21]. When benzylated 1-O-acetyl-D-hexopyranoses reacted with triethyl phosphite and trimethylsilyl trifluoromethanesulfonate as a catalyst the similar phosphorus insertion opened a way to seven-membered nucleoside phostones [22]. ...
