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At least 595 records · Page 33Linked to original sources
PubMed1981

Sulfonate analogues of adenosine nucleotides as inhibitors of nucleotide-binding enzymes.

2-(Adenin-9-yl)ethanesulfonic acid (1), 3-(adenin-9-yl)propanesulfonic acid (2), 9-(5-deoxy-beta-D-ribofuranosyl)-adenine-5'-sulfonic acid (3), and 9-(3-deoxy-beta-D-arabinofuranosyl)adenine-3'-sulfonic acid (4) were prepared by reaction of the corresponding chlorides by sodium sulfite (1-3) or by reaction of an epoxide with sodium hydrogen sulfite (4). They inhibited a typical nucleotide-binding enzyme, horse liver alcohol dehydrogenase, with inhibition constants in the range of 0.18-4.9 mM at pH 8, 25 degrees C.

Adenine Nucleotides↗
PubMed1983

2-haloethylating agents for cancer chemotherapy. 2-haloethyl sulfonates.

Because certain (2-chloroethyl)triazenes and (2-haloethyl)nitrosoureas have high antineoplastic activity, 2-chloroethyl and 2-fluoroethyl sulfonates were prepared to try to develop additional types of 2-haloethylating agents. In this initial study, it was demonstrated that antineoplastic activity much superior to that of the prototype, 2-chloroethyl methanesulfonate, could be found among 2-chloroethyl sulfonates. Among a variety of 2-chloroethyl alkane- and arenesulfonates, several substituted methanesulfonates displayed significant activity against P388 leukemia in mice; the chloromethanesulfonate showed high activity (T/C = 218%). None of the arenesulfonates were active in this test.

Animals↗
PubMed2005

Docking and 3-D QSAR studies on indolyl aryl sulfones. Binding mode exploration at the HIV-1 reverse transcriptase non-nucleoside binding site and design of highly active N-(2-hydroxyethyl)carboxamide and N-(2-hydroxyethyl)carbohydrazide derivatives.

Three-dimensional quantitative structure-activity relationship (3-D QSAR) studies and docking simulations were developed on indolyl aryl sulfones (IASs), a class of novel HIV-1 non-nucleoside reverse transcriptase (RT) inhibitors (Silvestri, et al. J. Med. Chem. 2003, 46, 2482-2493) highly active against wild type and some clinically relevant resistant strains (Y181C, the double mutant K103N-Y181C, and the K103R-V179D-P225H strain, highly resistant to efavirenz). Predictive 3-D QSAR models using the combination of GRID and GOLPE programs were obtained using a receptor-based alignment by means of docking IASs into the non-nucleoside binding site (NNBS) of RT. The derived 3-D QSAR models showed conventional correlation (r(2)) and cross-validated (q(2)) coefficients values ranging from 0.79 to 0.93 and from 0.59 to 0.84, respectively. All described models were validated by an external test set compiled from previously reported pyrryl aryl sulfones (Artico, et al. J. Med. Chem. 1996, 39, 522-530). The most predictive 3-D QSAR model was then used to predict the activity of novel untested IASs. The synthesis of six designed derivatives (prediction set) allowed disclosure of new IASs endowed with high anti-HIV-1 activities.

Binding Sites↗
PubMed1996

2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones.

The synthesis and the evaluation of cytotoxicity and anti-HIV-1 activity of new aryl pyrrolyl (8) and aryl indolyl (9) sulfones are reported. Preparation of above sulfones was achieved by reacting arylsulfonyl chlorides with substituted pyrroles and indoles or by condensing sulfonamides with 2,5-dimethoxytetrahydrofuran in glacial acetic acid according to the Clauson-Kaas method. Chemical requisites relevant to the anti-HIV-1 activity of these compounds are both a 2-sulfonyl-4-chloroanilino moiety and an alkoxycarbonyl group at position 2 of the pyrrole ring. The best activity and selectivity were obtained with ethoxycarbonyl and isopropoxycarbonyl substituents. Substitutions at the amino group of the pharmacophore moiety led to inactive products (alkylation) or weakened (acylation) anti-HIV-1 activity. Among test derivatives, 16 compounds showed EC50 values ranging between 10 and 1 microM, and five (8b',d',f',h'j') showed EC50S in the sub-micromolar range. The compounds were active against HIV-1, both wild type and AZT-resistant strains, but not against HIV-2. Moreover, in enzyme assays they potently inhibited the HIV-1 recombinant reverse transcriptase, were 10 times less active against enzymes from nevirapine- and TIBO-resistant strains, and were totally inactive against the HIV-2 recombinant enzyme. Interestingly, some compounds (8r'-y') were inactive against the recombinant reverse transcriptase while being active in tissue culture.

Antiviral Agents↗
PubMed1999

Conceptually new sulfone analogues of the hormone 1alpha, 25-dihydroxyvitamin D(3): synthesis and preliminary biological evaluation.

A conceptually new series of vitamin D(3)-like nonfluorinated and fluorinated 16-ene side chain tert-butyl sulfones 3-7 has been synthesized. Even though these novel C,D-ring side chain analogues of the hormone 1alpha,25-dihydroxyvitamin D(3) (1,1,25D(3)) lack a terminal OH group, thought previously to be essential for high biological activity, they are highly antiproliferative and, in several cases, transcriptionally active in vitro but desirably noncalcemic in vivo. The side chain sulfone group may be binding to the nVDR as a hydrogen-bond acceptor, in contrast to the hydrogen-bond donor function of the 25-OH group of natural 1,25D(3).

Animals↗
PubMed2005

A diastereoselective and general route to 5-amino-5-deoxysugars: influence of C-3 substitution on the addition of amines to C-5 of vinyl sulfone-modified hex-5-enofuranosyl carbohydrates.

In the synthesis of vinyl sulfone-modified hex-5-enofuranosides, the E/Z ratios of the products are influenced by the stereoelectronic property of a group present at the C-3 position. This observation has been utilized to influence the diastereoselectivity of addition of amines to C-5 of vinyl sulfone- modified hex-5-enofuranosides, which are efficient Michael acceptors. The stereoelectronic effect of OMe attached to the beta-face of C-3 (gluco derivative) is sufficient to impose diastereoselectivity overwhelmingly in favor of l-ido-aminosugars when the Michael acceptor is reacted with both primary and secondary amines. 3-O-Benzylated gluco derivative is also effective in producing l-ido-aminosugars but only in reactions with primary amines. The selectivity is lost when an allo derivative with OBn at the alpha-face of C-3 is used. Selected products were desulfonated to establish this new approach as a general and versatile strategy for accessing 5-amino-5-deoxysugars.

Amines↗
PubMed2005

Sulfone coupling and double-elimination strategy for carotenoid synthesis.

[Reaction: see text]. A highly efficient synthetic method of carotenoid compounds has been developed on the basis of the sulfone coupling and double-elimination strategy. This method highlighted the sulfone-mediated coupling with the novel C(10) dialdehyde, 2,7-dimethyl-4-octenedial, which was easily prepared and efficiently utilized in the synthesis of the conjugated polyene chains.

Carotenoids↗
PubMed2006

New glycomimetics: anomeric sulfonates, sulfenamides, and sulfonamides.

The synthesis of a variety of new 1-thio-D-glucopyranose derivatives oxidized at the sulfur atom is described, including seven 1-C-sulfonic acids, three sulfonate esters, three sulfinate esters, an S,S'-diglycosyl thiolsulfonate and thiolsulfinate, four S-glycosyl sulfenamides, an S-glycosyl sulfinamide, and two S-glycosyl sulfonamides. These compounds possess unusual anomeric functionality that might be resistant or even inhibitory to normal enzymatic carbohydrate processing, and therefore, they may be of future use in studies of enzyme inhibition, structure, mechanism, and function.

Carbohydrates↗
PubMed2000

Stereoselective synthesis of cyclic ethers using vinylogous sulfonates as radical acceptors: effect of E/Z geometry and temperature on diastereoselectivity.

Treatment of the E-vinylogous sulfonates 1a-g with tris(trimethylsilyl)silane and triethylborane, in the presence of air, furnished the cyclic ethers 2/3a-g with good to excellent diastereoselectivity favoring the cis-isomer 2. This study demonstrated the level of stereocontrol in a 6-exo radical cyclization and may be attributed to the type of radical intermediate. Hence, the modest selectivity obtained for the cyclization of 1e may be a function of the acyl radical geometry (sp2) and high inversion barrier (29 kcal/mol) as compared to the alkyl (1 kcal/mol) and vinyl (2.9 kcal/mol) radicals. This is consistent with the acyl radical cyclization having an earlier transition state than the corresponding alkyl and vinyl radicals. The modest diastereoselectivity can be improved dramatically using the Z-vinylogous sulfonate (> or =34:1; R = Ph) to promote kinetic trapping of the s-trans rotamer I and III, respectively (Figure 1). The 5-exo alkyl radical cyclization reaction under nonreductive Keck-allylation conditions was also examined, in which 8 was formed in 91% overall yield. This transformation provides a convenient method for in situ homologation and should be applicable to target directed synthesis.

Cyclization↗
PubMed2004

Chemical modification of the surface of a sulfonated membrane by formation of a sulfonamide bond.

This paper describes a novel approach for the surface modification of a cation-exchange membrane, bearing sulfonate groups, by a cationic layer. The modification procedure involved the chlorosulfonation of the sulfonate groups of the base membrane with thionyl chloride, followed by a reaction with a diamine to yield a sulfonamide bond and a terminal amine. The latter could be quaternized by reaction with methyl iodide or protonated by soaking in acidic media. The membranes were characterized in detail by attenuated total reflectance Fourier transform infrared and X-ray photoelectron spectroscopies as well as elemental analysis to confirm that the above reactions occurred. The selectivity of these membranes toward the electrochemically assisted transport of protons versus Zn2+ metallic cations was determined during an electrodialysis in a two-compartment electrochemical cell. The data indicate a significant decrease of the transport of the metallic cations following modification of the membrane with the cationic layer. The later allows for the transport of protons from the catholyte to the anolyte compartment with much improved selectivity since the divalent cations are excluded from the membrane due to the electrostatic barrier of the cationic layer.

Diamines↗
PubMed2002

Synthesis of cyclic sulfones by ring-closing metathesis.

A general and highly efficient synthesis of cyclic sulfones based on ring-closing metathesis has been developed. The synthetic utility of the resulting cyclic sulfones was demonstrated by their participation in stereoselective Diels-Alder reactions and transformation to cyclic dienes by the Ramberg-Bäcklund reaction.

Molecular Structure↗
PubMed2003

Anomeric configuration-directed diastereoselective C-C bond formation in vinyl sulfone-modified carbohydrates: a general route to branched-chain sugars.

[structure: see text] This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy group. This novel concept of anomeric configuration-directed stereocontrolled carbon-carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched-chain sugars and densely functionalized carbohydrates.

Carbohydrate Conformation↗
PubMed2003

Novel approach for asymmetric synthesis of fluorinated beta-amino sulfones and allylic amines.

[reaction: see text] Enantiomerically pure gamma-fluoroalkyl beta-amino sulfones are readily synthesized in three steps starting from fluorinated imidoyl chlorides and arylmethyl sulfones. A complementary two-step sequence starting from chiral fluorinated beta-amino sulfoxides has also been developed. To illustrate the application of this procedure, a new method for the synthesis of alpha-fluoroalkyl allylic amines in optically pure form involving a Julia methylenation-desulfonylation reaction is presented.

Allyl Compounds↗
PubMed2006

New synthesis of beta-sultams from pentafluorophenyl sulfonates.

A stereoselective one-pot synthesis of substituted 1,2-thiazetidine 1,1-dioxides (beta-sultams) has been achieved from heterocyclic pentafluorophenyl (PFP) sulfonates. Mild N-O bond cleavage of isoxazolidines followed by intramolecular cyclization of the amine onto the PFP demonstrates the potential utility for using the PFP sulfonate as a valuable precursor to sulfonamides. [reaction: see text].

Anti-Bacterial Agents↗
PubMed2003

Highly diastereoselective addition of nitromethane anion to chiral alpha-amidoalkylphenyl sulfones. Synthesis of optically active alpha-amino acid derivatives.

Optically active syn-alpha-amidoalkylphenyl sulfones can be prepared from chiral aldehydes in anhydrous conditions using benzenesulfinic acid. These sulfones in basic conditions give N-acylimines that react with sodium methanenitronate to afford the corresponding nitro adducts with high anti diastereoselectivity. PM3 semiempirical calculations provide a rationale for the observed opposite stereoselectivity. The obtained nitro derivatives undergo a Nef reaction followed by a methylation giving optically active beta-hydroxy-alpha-amino acid and alpha,beta-diamino acid esters in good yield. These amino acid derivatives are important building blocks for the preparation of biologically active compounds.

Aldehydes↗
PubMed2005

Detoxification pathways of the phytoalexins brassilexin and sinalexin in Leptosphaeria maculans: isolation and synthesis of the elusive intermediate 3-formylindolyl-2-sulfonic acid.

Brassilexin and sinalexin are among the most potent antifungal phytoalexins produced by crucifer plants. Nonetheless, the crucifer pathogen Leptosphaeria maculans(Desm.) Ces. et de Not. (asexual stage Phoma lingam(Tode ex Fr.) Desm.) is able to detoxify these phytoalexins. To understand and control these reactions, the elusive brassilexin and sinalexin detoxification pathways in L. maculans were investigated and compared to those of the synthetic derivatives 8-methylbrassilexin and 8-acetylbrassilexin. The chemical structures, syntheses and antifungal activities of the metabolic intermediates, including the most polar metabolite identified thus far, 3-formylindolyl-2-sulfonic acid, were established. Our overall findings suggest that the first detoxification step of brassilexin involves its reductive bioconversion to 3-aminomethyleneindole-2-thione, followed by hydrolysis and oxidation to the water soluble metabolite 3-formylindolyl-2-sulfonic acid.

Ascomycota↗