Sudan Black B: chemical structure and histochemistry of the blue main components.

Sudan Black B contains two blue main components, SSB-I and SSB-II. Their chemical structures were determinated by the aid of two-dimensional thin-layer chromatography, column chromatography, absorption, IR, mass, H1-NMR, and C13-NMR spectroscopy and were proved by alternate synthesis. SSB-I has been found to be 2,3-dihydro-2,2-dimethyl4-[(4-phenylazo-1-naphthalenyl)-azol]-1H-perimidine. For SSB-II was confirmed the known structure 2,3-dihydro-2,2-dimethyl-6-[(4-phenylazo-1-naphthalenyl)-azo]-1H-permidine. Relations of chemical structure of SSB-I and SSB-II to their staining properties are discussed.     

Effect of Foliar Application of Carbofuran and a Related Compound on Plant-parasitic Nematodes under Greenhouse and Growth Chamber Conditions

Greenhouse and growth chamber studies were made to investigate the downward systemic nematicidal activity of carbofuran and its analog 2,3-dihydro-2,2-dimethyl-7-benzofuranyl [(di-n-butyl)-4-aminosulfenyl] carbamate against Meloidogyne incognita, Tylenchorhynchus claytoni, and Pratylenchus penetrans. Oxamyl was used as standard in tests with T. claytoni. Both carbofuran and its analog reduced all three plant-parasitic species when plant foliage was sprayed with chemical suspension of 1,200, 2,400 or 4,800 ppm. The studies show that fewer chemical applications were required to reduce populations of P. penetrans than to reduce populations of T. claytoni. Oxamyl was somewhat less active than either carbofuran or its analog.     

Lignans from machilus thunbergii

Five new lignans, machilin A[(2S,3R)-2,3-dimethyl-1,4-dipiperonyl-butane], machilin B [(2S,3S)-2,3-dihydro-7-methoxy-3-methyl-2-piperon threo-2-(2-methoxy-4-trans-propenylphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propan-1-ol], machilin E (erythro-1-acetoxy-2-(2-methoxy-4-trans-(3-hydroxy-1-propenyl)phenoxy]-l-piperonylpropane) were isolated from the bark of Machilus thunbergii and their structures were characterized.     

Structure of Aurasperone C

Aurasperone C (III) shows properties closely related to those of aurasperone B (II) and gave dianhydro compound (V) on hydrochloric acid treatment. Partial methylation of (V) with methyl iodide afforded a monomethyl ether identical with aurasperone A (I).

NMR studies, including solvent induced methoxyl shifts, indicate the structure of (III) to be 2,2′-dimethyl-2,2′,5,5′-,8-pentahydroxy-6,6′,8-trimethoxy-7,10′-bi[2,3-dihydro-4H-naphtho[2,3b]pyran-4-one], in which the 8-methoxyl of aurasperone B is replaced by a hydroxyl group.     

Induction of carbofuran oxidation to 4-hydroxycarbofuran by Pseudomonas sp. 50432

Pseudomonas sp. 50432 biotransformed a highly toxic pesticide, carbofuran (2,3-dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate) to 7-phenol (2,3-dihydro-2,2-dimethyl-7-hydroxy benzofuran) and several unknown metabolites. One of the unknown metabolites identified by gas chromatography/mass spectroscopy was 4-hydroxycarbofuran (2,3-dihydro-2,2-dimethyl-4-hydroxybenzofuran-7-yl methylcarbamate). It had a mass (237) similar to 3-hydroxycarbofuran and 5-hydroxycarbofuran but different fragmentation patterns. This is the first report in which an inducible oxidative enzyme, hydroxylase, mediated the conversion of carbofuran to 4-hydroxycarbofuran. A second constitutively synthesized enzyme hyrolase transformed carbofuran to 7-phenol.     

Chromones from the tubers of Eranthis cilicica and their antioxidant activity

Chemical studies on the constituents of Eranthis cilicica led to isolation of ten chromone derivatives, two of which were previously known. Comprehensive spectroscopic analysis, including extensive 1D and 2D NMR data, and the results of enzymatic hydrolysis allowed the chemical structures of the compounds to be assigned as 8,11-dihydro-5-hydroxy-2,9-dihydroxymethyl-4H-pyrano[2,3-g][1]benzoxepin-4-one, 5,7-dihydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-enyl]-2-methyl-4H-1-benzopyran-4-one, 5,7-dihydroxy-2-hydroxymethyl-8-[(2E)-4-hydroxy-3-methylbut-2-enyl]-4H-1-benzopyran-4-one, 7-[(β-d-glucopyranosyl)oxy]-5-hydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-enyl]-2-methyl-4H-1-benzopyran-4-one, 7-[(β-d-glucopyranosyl)oxy]-5-hydroxy-2-hydroxymethyl-8-[(2E)-4-hydroxy-3-methylbut-2-enyl]-4H-1-benzopyran-4-one, 9-[(O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]methyl-8,11-dihydro-5,9-dihydroxy-2-methyl-4H-pyrano[2,3-g][1]benzoxepin-4-one, 8,11-dihydro-5,9-dihydroxy-9-hydroxymethyl-2-methyl-4H-pyrano[2,3-g][1]benzoxepin-4-one, and 7-[(O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]methyl-4-hydroxy-5H-furo[3,2-g][1]benzopyran-5-one, respectively. The isolated compounds were evaluated for their antioxidant activity.     

Chromones from the stems of Cassia fistula and their anti-tobacco mosaic virus activities

Three new chromones, 5-methoxy-2,2-dimethyl-7-(2-oxopropyl)-2,3-dihydrochromen-4-one (1), 5-methoxy-2,2-dimethyl-8-(2-oxopropyl)-2,3-dihydrochromen-4-one (2), and 1-(3,4-dihydro-5-methoxy-2,2-dimethyl-2H-chromen-7-yl)propan-2-one (3), together with four known chromones (4–7) were isolated from the stems of Cassia fistula. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compounds 1–5 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 5 exhibited high anti-TMV activity with inhibition rate of 30.8% at a concentration of 20 μM. The other compounds also exhibited potential anti-TMV activities with inhibition rates in the range of 15.6–22.1% at the same concentration.     

Pyrano-[2,3b]-pyridines as potassium channel antagonists

The design and synthesis of a series of highly functionalized pyrano-[2,3b]-pyridines is described. These compounds were assayed for their ability to block the I(Kur) channel encoded by the gene hKV1.5 in patch-clamped L-929 cells. Six of the compounds in this series showed sub-micromolar activity, the most potent being 4-(4-ethyl-benzenesulfonylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3b]-pyridine-6-carboxylic acid ethyl-phenyl-amide with an IC(50) of 378 nM.     

Synthesis and glycosidation of 1-deoxy-1-[(2,2-diacylvinyl)amino]-d-fructoses

The reactions of 1-amino-1-deoxy-d-fructose acetate (1) with methyl 3-methoxy-2-methoxycarbonylacrylate and 5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione in the presence of a base afforded 1-deoxy-1-[(2,2-dimethoxycarbonylvinyl)amino]- (2 and 1-deoxy-1-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethyl)amino]-d-fructose (3), respectively, in high yields. 1-Deoxy-1-[(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino]-d-fructose (4) was obtained (85%) by a transamination reaction between 1 and 5,5-dimethyl-2-phenylaminomethylene-1,3-cyclohexanedione in the presence of Et₃N. The isomeric composition of equilibrium solutions of 1–4 was established by ¹³C-n.m.r. spectroscopy. For all the compounds, the β-pyranose form was the main component in D₂O; the α-furanose, the β-furanose, and, for 1, the α-pyranose forms, were also present. The major constituents of 2 in (CD₃)₂SO solution were the β- and the α-furanose forms. Acetylation of 2 afforded the tetra-acetates of the α- and β-furanose forms, the 3,4,6-triacetates of the α- and β-furanose forms, the 3,4,5-triacetate of the β-pyranose form, and 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-[(2,2-dimethoxycarbonylvinyl)amino]-d-arabino-hex-1-enitol. Glycosidation of 2 with MeOHHCl afforded a mixture of methyl 1-deoxy-1-[(2,2-dimethoxycarbonylvinyl)amino]-α- (11α) and -β-d-fructofuranoside (11β), and methyl 1-deoxy-1-[(2,2-dimethoxycarbonylvinyl)-amino]-β-d-fructopyranoside (13). Compounds 11α and 13 were isolated as their tri-acetates (12 and 14, respectively). Deacetylation and removal of the N-protecting group of 12 gave methyl 1-amino-1-deoxy-α-d-fructofuranoside (∼54% from 2).     

Characterisation and X-ray crystallography of products from the Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside

Methyl 2,3-O-isopropylidene-alpha-D-mannofuranosidurononitrile [alternative name: methyl (5R)-5-C-cyano-2,3-O-isopropylidene-alpha-D-lyxofuranoside] (2), methyl 2,3-O-isopropylidene-alpha-D-mannofuranosiduronamide [methyl (5S)-5-C-carbamoyl-2,3-O-isopropylidene-alpha-D-lyxofuranoside; methyl (5S)-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosiduronamide] (3), methyl 2,3-O-isopropylidene-alpha-D-mannofuranosiduronic acid [methyl (5S)-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosiduronic acid] (4), methyl 5-deoxy-2,3-O-isopropylidene-5-ureido-beta-L-gulofuranosiduronamide [methyl (5R)-5-deoxy-2,3-O-isopropylidene-5-ureido-alpha-D-lyxo-hexofuranosiduronamide (5), and (4S,5S,6R)-5,6-dihydro-6-hydroxy-4,5-isopropylidenedioxy-4H-pyrido[2,1-e]imidazolidine-2',4'-dione [IUPAC name: (3aS,4R,8aS)-4-hydroxy-2,2-dimethyl-3a,8a-dihydro-4H-1,3-dioxa-4a,6-diaza-s-indacene-5,7-dione] (6), instead of the expected hydantoin derivative, were obtained from the Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside (1). The structure of 6 was deduced from NMR and mass spectral data and confirmed by X-ray crystallography. The configuration at C-5 in 2-5 was confirmed by establishing the 5S configuration of 3 by X-ray crystallography. Conformations of the six- and five-membered rings in 3 and 6 are also discussed.     

Synthesis of novel selenium containing sulfa drugs and their antibacterial activities

Synthesis of 3-[4-(N-substituted sulfamoyl)phenyl]-3,4-dihydro-4-oxo-7,9-dimethylpyri-do[3′,2′:4,5]selenolo[3,2-d]pyrimidines,7-[4-(N-substituted sulfamoyl)phenyl]-7,8-dihydro-8-oxo-3,4-diphenylpyrimido[4′,5′:4,5]selenolo [2,3-c]pyridazines and 1-[4-(N-substituted sulfamoyl)phenyl]-1,11-dihydro 11-oxo-4-methylpyrimido[4′,5′:4,5]selenolo[2,3-b]quinolines is reported. 4-Amino-N-pyrimidine-2-ylbenzene sulfonamide (a), 4-amino-N-(2,6-dimethylpyrimidin-4-yl)benzene sulfonamide (b), N-[(4-aminophenyl)sulfonyl] acetamide (c) with N-ethoxymethyleneamino of selenolo pyridine, selenolo pyridazine and selenolo quinoline derivatives respectively were obtained starting from 1-amino-N ⁴-substituted sulfanilamides. Spectroscopic data (IR, ¹H NMR, ¹³C NMR and Mass spectral) confirmed the structure of the newly synthesized compounds. Substituted pyrimidines, pyridazines and quinolines were screened for antibacterial activity against gram-positive and gram-negative bacteria. Selenolo derivative of N-[(4-aminophenyl)sulfonyl] acetamide (substitutent of sulfacetamide c) showed strong bactericidal effect against all the tested organisms. Selenolo[3,2-d]pyrimidin (substitutent a) showed a good bactericidal effect against Serratia marcescens, Staphylococcus aureus and Escherichia coli. Compounds selenolo[2,3-c]pyridazine (substitutent b), selenolo[2,3-b]quinoline(substitutents c)) exhibited a moderate bactericidal effect against Serratia marcescens. None of the synthesized seleno pyridazines has a considerable antimicrobial activity against the tested organisms. The minimum inhibitory concentration (MIC) of the most active compound-3-[4-(N-acetyl sulfamoyl)phenyl]-3,4-dihydro-4-oxo-7,9-dimethylpyrido[3′,2′:4,5]selenolo [3,2-d]pyrimidine was 10 mg ml⁻¹.     

Mineralization of Carbofuran by a Soil Bacterium

A bacterium, tentatively identified as an Arthrobacter sp., was isolated from flooded soil that was incubated at 35°C and repeatedly treated with carbofuran (2,3-dihydro-2,2-dimethyl-7-benzofuranyl N-methylcarbamate). This bacterium exhibited an exceptional capacity to completely mineralize the ring-labeled ¹⁴C in carbofuran to ¹⁴CO₂ within 72 to 120 h in a mineral salts medium as a sole source of carbon and nitrogen under aerobic conditions. Mineralization was more rapid at 35°C than at 20°C. No degradation of carbofuran occurred even after prolonged incubation under anaerobic conditions. The predicted metabolites of carbofuran, 7-phenol (2,3-dihydro-2,2-dimethyl-7-benzofuranol) and 3-hydroxycarbofuran, were also metabolized rapidly. 7-Phenol, although formed during carbofuran degradation, never accumulated in large amounts, evidently because of its further metabolism through ring cleavage. The bacterium readily hydrolyzed carbaryl (1-naphthyl N-methylcarbamate), but its hydrolysis product, 1-naphthol, resisted further degradation by this bacterium.     

Phytotoxic naphthopyranone derivatives from the coprophilous fungus Guanomyces polythrix.

Reinvestigation of the fermentation broth and mycelium of the coprophilous fungus Guanomyces polythrix, grown in static conditions, led to the isolation of several phytotoxic compounds, including two new naphthopyranone derivatives, namely (2S, 3R)-5-hydroxy-6,8-dimethoxy-2,3-dimethyl-2,3-dihydro-4H-naphtho[2,3-b]-pyran-4-one and (2S, 3R)-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydro-4H-naphtho[2,3-b]-pyran-4-one. The structures of the new compounds were established by spectral and chiroptical methods. In addition, the structure of 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ester was unambiguously determined by X-ray analysis. The isolates caused significant inhibition of radicle growth of two weed seedlings (Amaranthus hypochondriacus and Echinochloa crusgalli) and interacted with both spinach and bovine brain calmodulins.     

New Phenylpropanoid Glycosides from Illicium majus and Their Radical Scavenging Activities

Chemical investigation of the ethanol extract of the branch and leaves of Illicium majus resulted in the isolation of four new phenylpropanoid glycosides ( 1 – 4 ) and one new phenolic glycoside ( 9 ), along with 13 known ones. Spectroscopic techniques were used to elucidate the structures of the new isolates such as 3-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]propyl β-D-glucopyranoside ( 1 ), [(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methyl 2-O-α-L-rhamnopyranosyl-β-D-glucopyranoside ( 2 ), [(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-3-yl]methyl 2-O-α-L-rhamnopyranosyl-β-D-xylopyranoside ( 3 ), 3-[(2R,3S)-3-({[2-O-(4-O-acetyl-α-L-rhamnopyranosyl)-β-D-xylopyranosyl]oxy}methyl)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]propyl acetate ( 4 ), and 4-(2-hydroxyethyl)phenyl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside ( 9 ). Free radical scavenging activities of the isolates were elucidated through the DPPH assay method. The most active compounds, 1-O-caffeoyl-β-D-glucopyranose ( 17 ) and soulieana acid 1 ( 18 ), exhibited moderate radical scavenging activities (IC₅₀=37.7±4.4 μM and IC₅₀=97.2±3.4 μM, respectively). The antibacterial activities of the isolates against Staphylococcus aureus and Escherichia coli were also assessed, and no activity was shown at the measured concentration (<32 μg/mL).     

Two naphthopyran derivatives from Faramea cyanea

Four anthraquinones and two new products, faramol (3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran) and 7-methoxyfaramol (3,4-dihydro-3-hydroxy-7-methoxy-2,2-dimethyl-2H-naphtho[l,2-b]pyran), have been isolated from Faramea cyanea.     

Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity

Reaction of hydrazonoyl halides with 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and 2,3-diaminoquinazolin-4-one site-selectively afforded 3-substituted-7-(benzylidenamino)-1-phenyl-[1,2,4]triazolo[4,3-a]-pyrimidin-5(1H)-ones, [1,2,4,5]tetrazino[6,1-b]quinazolin-6(4H)-one, and 3-methyl-2-(4-substituted-phenylhydrazo)-[1,2,4]triazino[3,2-b]quinazolin-10-ones in good yields. The structures of the newly synthesized compounds were elucidated by chemical evidence and their IR, ¹H, ¹³C NMR, and MS spectra. Furthermore, some of the products were screened against different strains of bacteria and fungi.     

Synthesis of [18F]SU11248, a new potential PET tracer for imaging cancer tyrosine kinase

N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-[18F]fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide, a new potential positron emission tomography tracer for imaging cancer tyrosine kinase, has been prepared by the nucleophilic substitution of the nitro-precursor N-[2-(diethylamino)ethyl]-5-[(Z)-(5-nitro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide with K18F/Kryptofix 2.2.2 followed by a simple chromatography methodology combined solid-phase extraction with high-performance liquid chromatography purification procedures in 15-25% radiochemical yields.     

α-Glucosidase Inhibition by Usnic Acid Derivatives

This study investigated a set of new potential antidiabetes agents. Derivatives of usnic acid were designed and synthesized. These analogs and nineteen benzylidene analogs from a previous study were evaluated for enzyme inhibition of α-glucosidase. Analogs synthesized using the Dakin oxidative method displayed stronger activity than the pristine usnic acid (IC₅₀>200 μM). Methyl (2E,3R)-7-acetyl-4,6-dihydroxy-2-(2-methoxy-2-oxoethylidene)-3,5-dimethyl-2,3-dihydro-1-benzofuran-3-carboxylate ( 6b ) and 1,1′-(2,4,6-trihydroxy-5-methyl-1,3-phenylene)di(ethan-1-one) ( 6e ) were more potent than an acarbose positive control (IC₅₀ 93.6±0.49 μM), with IC₅₀ values of 42.6±1.30 and 90.8±0.32 μM, respectively. Most of the compounds synthesized from the benzylidene series displayed promising activity. (9bR)-2,6-Bis[(2E)-3-(2-chlorophenyl)prop-2-enoyl]-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one ( 1c ), (9bR)-3,7,9-trihydroxy-8,9b-dimethyl-2,6-bis[(2E)-3-phenylprop-2-enoyl]dibenzo[b,d]furan-1(9bH)-one ( 1g ), (9bR)-2-acetyl-6-[(2E)-3-(2-chlorophenyl)prop-2-enoyl]-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one ( 2d ), (9bR)-2-acetyl-6-[(2E)-3-(3-chlorophenyl)prop-2-enoyl]-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one ( 2e ), (6bR)-8-acetyl-3-(4-chlorophenyl)-6,9-dihydroxy-5,6b-dimethyl-2,3-dihydro-1H-[1]benzofuro[2,3-f][1]benzopyran-1,7(6bH)-dione ( 3e ), (6bR)-8-acetyl-6,9-dihydroxy-5,6b-dimethyl-3-phenyl-2,3-dihydro-1H-[1]benzofuro[2,3-f][1]benzopyran-1,7(6bH)-dione ( 3h ), (6bR)-3-(2-chlorophenyl)-8-[(2E)-3-(2-chlorophenyl)prop-2-enoyl]-6,9-dihydroxy-5,6b-dimethyl-2,3-dihydro-1H-[1]benzofuro[2,3-f][1]benzopyran-1,7(6bH)-dione ( 4b ), and (9bR)-6-acetyl-3,7,9-trihydroxy-8,9b-dimethyl-2-[(2E)-3-phenylprop-2-enoyl]dibenzo[b,d]furan-1(9bH)-one ( 5c ) were the most potent α-glucosidase enzyme inhibitors, with IC₅₀ values of 7.0±0.24, 15.5±0.49, 7.5±0.92, 10.9±0.56, 1.5±0.62, 15.3±0.54, 19.0±1.00, and 12.3±0.53 μM, respectively.     

Effect of Foliar Applications of Carbofuran and a Related Compound on Plant-parasitic Nematodes under Microplot and Field Conditions

Studies were conducted to investigate the basipetal translocation of nematicidal activity from foliar treatments of carbofuran and its analog, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ([dibutylamino]thio)methyl carbamate, on corn in microplot studies and on tobacco and potato in field trials. Two and three foliar applications of either product at 2,400 μg/ml (9-20 Kg ai/Ha) significantly reduced populations of Pratylenchus penetrans in roots and populations of Tylenchorhynchus claytoni, Xiphinema americanum, and Hoplolaimus sp. in soil. In most cases there was no difference in control between two or three chemical applications. Foliar treatments with carbofuran were equivalent to, or better than, soil treatment, although rates of applications were different.     

Synthesis and Antiviral Evaluation of Novel 2,3-Dihydroxypropyl Nucleosides from 2- and 4-Thiouracils

Regioselective alkylation of 2-thiouracils 1a–c and 4-thiouracils 7a,b with 2,3-O-isopropylidene-2,3-dihydroxypropyl chloride (2) afforded 2-{[(2,2-Dimethyl-1,3-dioxolan-4-yl) methyl]thio}pyrimidin-4(1H)-ones 3a–c and 4-{[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]thio} pyrimidin-2(1H)-ones 8a,b, respectively. Further alkylation with 2 and/or 2,3-O-isopropylidine-1-O-(4-toluenesulfonyl)-glycerol (4) gave the acyclo N-nucleosides 5a–c and 9a,b whose deprotection afforded 6a–c and 10a,b. 2-(Methylthio)pyrimidin-4(1H)-ones 11a–c and 4-(methylthio)pyrimidin-2(1H)-ones 14a,b were treated with 2 and/or 4 to give 12a–c and 15a,b which were deprotected to give 13a–c and 16a,b. Pyrimidine-2,4(1H,3H)-dithiones 17a–c were treated with two equivalents of 2 to give 2,4-bis{[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]thio}pyrimidines 18a–c. Deprotection of compounds 18a–c gave 2,4-bis[(2,3-dihydroxypropyl)thio]pyrimidines 19a-c. The activity of the deprotected nucleosides against Hepatitis B virus was evaluated and showed moderate inhibition activity against HBV with mild cytotoxicity.