Futalosine and its derivatives, new nucleoside analogs

Futalosine, a new nucleoside analog, was isolated from a fermentation broth of Streptomyces sp. MK359-NF1. Some chemical derivatives of futalosine were prepared. 6-O-Methylfutalosine methylester inhibited growth of HeLa-S3 cells in vitro (IC50 = 19.5 micrograms/ml) in contrast to the weak activity of futalosine. 6-O-Methylfutalosine methylester at concentrations higher than 10 micrograms/ml inhibited incorporation of 3H-TdR and 3H-UR but not 3H-Leu in the acid-soluble fractions of HeLa-S3 cells.     

Reactions of salicylamides with thionyl chloride

A series of compounds having the 1,2,3-benzoxathiazin-4 (3H) one 2-oxide structure have been synthesized by the interaction of thionyl chloride with the appropriate salicylamide. Some properties of these compounds as well as some by-products are described.     

Chlorination and oxidation of some sulfurcontaining tetrachloropyridine derivatives

In the chlorination of 4-methyl- and 4-chloroformylmethylenethiotetrachloropyridines, the chlorine atom enters the methyl or methylene group. In the case of the 4-(p-chlorobenzyl)-thio derivative, the molecule is cleaved to give tetrachloropyridine-4-sulfenyl chloride. Hydrogen peroxide oxidizes substituted benzyl- and ethoxycarbonylmethylenethiotetrachloropyridines to the corresponding sulfones, while nitric acid gives a mixture of tetrachloropyridinesulfonic acid and the corresponding benzole acid. quantitative yields (Table 2).Translated from Khimiya Geterotsiklicheskikh Soedinenii,No.8, pp. 1094–1098, August, 1972.     

Reaction of cyanuryl chloride and some of its monosubstituted derivatives with toluene

The Friedel-Crafts reaction of cyanuryl chloride and some of its monosubstituted derivatives with toluene was studied. It is shown that the type and character of the substituent in the 6 position of the starting derivatives of cyanuryl chloride have a strong effect on the course of the reaction. The reaction of cyanuryl chloride and its phenyl and phenoxy derivatives with toluene leads smoothly to the formation of 2,4,6-tris- and 2-substituted 4,6-bis(4-methylphenyl)-sym-triazines. 4,6-Bis(4-methylphenyl)2-oxo-2,3-dihydro-sym-triazine is formed in the case of alkoxy-substituted cyanuryl chlorides. In the case of amino derivatives of cyanuryl chloride the reaction with toluene takes place only upon prolonged refluxing and gives the final products in low yields.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 558–561, April, 1979.     

The reactions of C-methylheterocycles with thionyl chloride. Part 3. The transformation of some five-and six-membered heterocycles

Reactions of various five-and six-membered C-methylheterocycles with hot thionyl chloride gave chlorothio intermediates which were not characterized but which gave 1,2,4-thiadiazole derivatives when reacted with amidines and gave thioamides when reacted with amines. When 2,3-dimethyl-6-ethoxycarbonylimidazo-[4,5-b]pyridine ( 26 ) was treated with thionyl chloride a trisulphane 27 was isolated.     

Pyrazine nucleoside analogs. Synthesis and reactions of some 5-thio-substituted pyrazines

5-Benzylthio-1,2-dihydro-2-oxopyrazine ( 8 ) was prepared from 2-amino-5-bromopyrazine by sequential treatment with sodium thiobenzylate and diazotization. Condensation of the silyl derivative of 8 with a protected 2-deoxyribofuranosyl chloride gave α and β anomers of 5-benzylthiopyrazine nucleosides. Reaction of 2,5-dichloropyrazine 4-oxide with sodium thiobenzylate followed by hydrolysis gave 5-benzylthio-1,2-dihydro-2-oxopyrazine 4-oxide ( 16 ).     

Reaction of 2-thiobenzazoles with thionyl chloride

A new reaction in the benzimidazole series, viz., replacement of the mercapto group by chlorine by the action of thionyl chloride on 2-thiobenzimidazoles, was discovered. Benzoxazolone is formed by treatment of 2-thiobenzoxazole with thionyl chloride, and 2,2-dithiobis(2-benzothiazole) is formed from 2-thiobenzothiazole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1047–1050, August, 1985.     

Chlorination of some benzene derivatives by chlorine fluosulfate

Conclusions Exhaustive chlorination is observed when chlorine fluosulfate is reacted with 1,3,5-trichlorobenzene and nitrobenzene under mild conditions.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1160–1161, May, 1982.     

Mass spectrometry of nucleoside derivatives. Seleno analogs of purine and pyrimidine bases and nucleosides

Mass spectra of certain selenobases and selenonucleosides, and some of their trimethylsilyl and O,N-permethyl derivatives have been studied from the standpoint of structural characterization, and in order to ascertain the influence of selenium on normal fragmentation patterns. Molecular ion abundances of the selenouracils are intermediate between those of the corresponding oxygen and sulfur analogs. Fragmentation processes are similar to those of the corresponding normal bases and nucleosides but with additional ions resulting from expulsion of Se or SeH in most cases. Trimethylsilylation occurs at approximately the same rate as for normal bases and nucleosides but the products show decreasing stability with prolonged heating. A least squares procedure is demonstrated which generates monoisotopic mass patterns and assists in interpretation of the mass spectra.     

Synthesis and some properties of acrylic and methacrylic derivatives of chlorophos and its analogs

Conclusions The reaction of chlorophos and its analogs with the acid chlorides of the acrylic, methacrylic and-fluoroacrylic acids gave some new unsaturated compounds that possess fungicidal action.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 883–886, April, 1973.     

Synthesis of hindered hydrazones and their reaction with thionyl chloride

Hydrazones 12a–c and ketazines 13a–c were prepared by the reaction of ketones 11a–c with hydrazine hydrate depending on the temperature and the reaction time. Some ketone (aryl)hydrazone derivatives 14a,c,e reacted with thionyl chloride to afford the chlorothiadiazoline derivatives 15a–c . Surprisingly, the chlorine atom in the latter compounds was found to undergo smooth nucleophilic substitution, and by boiling these compounds in absolute ethanol gave the corresponding ethoxythiadiazoline derivatives 16a–c . The structure of the ethoxythiadiazoline 16b was confirmed by single crystal X‐ray determination. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:223–228, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10125     

Synthesis of novel 1,3,4-oxadiazole derivatives and their nucleoside analogs with antioxidant and antitumor activities

A series of new (1,3,4-oxadiazol-2-yl)-1H-benzo[h]quinolin-4-one derivatives were synthesized, including glucose and xylose hydrazones that were obtained by the reaction of hydrazides with monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded substituted oxadiazoline derivatives. The newly synthesized compounds were evaluated for their antioxidant properties and cytotoxicity, and showed moderate to high activities.     

Synthesis of acrylic and α-substituted acrylic derivatives of chlorophos and some of its analogs

Conclusions The corresponding acrylic and-substituted acrylic derivatives were obtained from the reactions of acrylyl, methacrylyl, and-fluoracrylyl chlorides with chlorophos and some of its analogs; the physicochemieal constants of the products are presented.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2616–2618, November, 1968.