SU1109410A1 - Process for preparing n-alkyl-n-(beta-d-glycosyl)-n-nitroso urea - Google Patents

Abstract

METHOD OF OBTAINING N-ALKYL; -N- (ji-D-GLYCOSYL) -N-NITROZOMOCHEVINA of the general formula RNH-CONRi N0 where R is the residue of D-galactose, D-glucose, B-xylose, R (is methyl, ethyl, propyl, butyl. Including nitrosation production , aqueous alkylene urea with sodium nitrite in the presence of glacial acetic acid, characterized in that, with a chain simplifying the process and expanding the range of the target product, the corresponding monosaccharide is reacted with an alkyl urea formula NH2-CO-NHR, where the presence of m-nitroaniline and concentrated hydrochloric acid Ota, followed by nitrosation floor (A chennyh alkylmochevin derivatives.

Description

The invention relates to an improved method of N-ania-Ji-N- (j3-D-rnHKO3HJi) N-HHTpo3O urea, which can be used in medicine as potential antitumor drugs, and also as initial ones in the synthesis of biologically active compounds.

1- A known method of producing N-alKHJi-N- (b-D-glycosyl) -K-nitrosureas (where alkyl; methyl, butyl, and glycoyl: xylose in a gtpose) involves the hydrogenation of poly-0-acetyl-5- glycosyl aprons in the presence of platinum oxide, in the interaction according to 11, of the glycine derivative of glucosylamine with alkyliso-yanates, in / isedetylation of the resulting glycosylurea derivative and its subsequent nitrosation with POM. Sodium nitrite in the presence of glacial acetic acid.

The yield of the product is 62% fl,

Reduction of a known method is the complexity and multistage stage of the floor 1 of the target product, as well as the use of platinum oxide from the catalyst,

Purpose) 13oС1тени - simplifying the process and pa.cunipem-ie the range of the target product.

.

The spruce tree is obtained by the fact that according to the method for producing M-alkyl-M- (hb-1) -glycosyl) -N-nitroseureas of the formula

R-t4H-CO-N-R,

N0

where R is the residue of P-galactose, B-glucose, B-xylose, R.- | - methyl, ethyl, propyl, butyl, including the pitrozirovaniye of alkyl derivatives with the help of nitrite carl in the presence of glacial acetic acid, osua alkyl urea unsubstituted monosaccharide of formula

NHR

WITH

 g

where, it has the above meanings in the presence of m-nitroaniline and conceptual hydrochloric acid with subsequent nitrosation of the resulting arylureas derivatives,

II p and measures 1. N-Methyl-N- (fb-I) -glucosyl) -N-nitrosourea

A mixture of 3.6 g of glucose, 1.8 g of metsturea, 0.2 g of l-nitroaniline and 0.13 g of concentrated hydrochloric acid in 20 ml of methanol is boiled

30 min. The precipitated amount of 2.85 g is separated, then 10 ml of glacial acetic acid, 3 ml of distilled water, 1.65 g of sodium nitrite are added and stirred at -2 ° C

2h The solution is evaporated, the residue is recrystallized from alcohol. Output 0%. M.p. 180 ° C with decomposition.OD, 19 (water). RP 0.56 paper chromatography (system: benzene-butanol-pyridine-water, 1: 5: 3: 5). Found,%: N 15.62. Calculated,%: N 15.84.

Example 2. N-Methyl-N- (p, -D-galactosyl) -N-nitrosourea.

A mixture of 3.6 g of galactose, 1.8 g of methyl urea. O, 1 g m -nitroanilina and O, 15. ml of concentrated hydrochloric acid in 10 ml of methanol was boiled for 15 minutes. The precipitated amount of 3.2 g is separated, then 15 ml of glacial acetic acid, 3 MP of distilled water, 1.86 g of sodium nitrite are added and stirred at -1 ° C for 2 hours. The precipitate is filtered, washed with alcohol. Yield 67%. M.p. 12ГС.1ас1д 21,8 ° (water). S.f 0.53 (under the conditions of Example 1). Found,%: N 15.50. Calculated,%: N 15.84.

Example 3. N-Methyl-N- & -D-xylosyl) -N-nitrosourea.

A mixture of 3 g of xylose, 1.7 g of methyl urea, 0.08 g of m-nitroaniline, 0.08 ml of concentrated hydrochloric

acid in 12 ml of ethanol

boil until the precipitate is completely dissolved. The mixture is cooled to room temperature, the precipitated amount of 2.55 g is separated, then 12 ml of glacial acetic acid, 2.3 ml of distilled water, 1.79 g of sodium nitrite are added and stirred at 2 hours. The precipitate is filtered, recrystallized from alcohol.

Yield 62%. M.p. 109 ° C with decomposition.

Мр -21.9 (water) .iij 0.66 (in the conditions of example 1). Found,%: N 17.62, Vyisleno,%: N 17.87,

Example 4, N-Ethyl-K - & - D-kc-tosyl) -N-nitrosourea.

A mixture of 3 g of KS1-SHOZY, 1.9 g of ethyl urea, 0.3 g of M-nitroaniline and 0.2 ml of concentrated hydrochloric 3 1109D acid is boiled in 15 1 × of ethyl alcohol for 10 minutes. A precipitate in the amount of 2.8 g is separated, then 15 ml of glacial acetic acid, 2.5 ml of distilled water, 1.74 g of sodium nitrite are added and stirred at O 2 hours. The solution is evaporated and recrystallized from alcohol. Yield 80%. M.p. JUAS with decomposition .r 0.76. , 6 ° (water). Found,%: W16.42. ° Calculated,%: W 16.86. Example 5. A mixture of 3.6 g of glucose, 2.3 g of propyl urea, 0.2 g of M-nitroaniline and 0.2 MP of concentrated hydrochloric acid in 1 ml of methanol was boiled for 55 minutes. The precipitated amount in the amount of 2.6 g is separated, then 15 ml of glacial acetic acid, 3 ml of distilled water, 1.8 g of sodium nitrite are added and stirred at -IC 2 hours. The solution is evaporated, the residue is recrystallized from alcohol. Yield 80%. M.p. 110 ° C with decomposition. (at ) . Example 6. A mixture of 3.6 g of glucose, 2.8 g of butylurea, 0.2 g of m-nitroaniline and 0.15 mp of concentrated hydrochloric acid in 10 ml of methanol was boiled for 20 minutes. 3 g of precipitated precipitate is separated, then 15 mp of acetic acid (ice), 5 ml of distilled water, 1.8 g of sodium nitrite are added and stirred at -HC for 2 hours. The solution is evaporated and the residue is recrystallized from alcohol. -Exit 90%. (in CHj, OH) ..

Claims (1)

METHOD FOR PRODUCING N-ALKyl-, -N- 9¾ -D-Glycosyl) -N-Nitrosourea of the General Formula ίRNH-CO NO ’where R is the remainder of D-galactose, D-glucose, D-xylose, ' R <- methyl, ethyl, propyl, butyl, including nitrosation of derivatives of alkylureas with sodium nitrite in the presence of glacial acetic acid, characterized in that, in order to simplify the process and expand the assortment of the target product, the corresponding monosaccharide is reacted with an alkyl urea of the formula NH ₂ - CO - NHR, where it has the above meanings, in the presence of m-nitroaniline and concentrated hydrochloric acid, followed by nitrosation of the obtained derivatives of alkylureas. th 11094 10