Preparation of isomeric 3-aminopropylamino derivatives of 9-(RS)-(2,3-dihydroxypropyl)adenine

1983 ◽  
Vol 48 (7) ◽  
pp. 1910-1921 ◽  
Author(s):  
Antonín Holý
Keyword(s):  
Acid Hydrolysis ◽  
Bromo Derivative ◽  
Derivatives Of ◽  
Subsequent Acid

Treatment of 9-(RS)-(2,3-dihydroxypropyl)adenine (III) with bromine in water afforded the 8-bromo derivative IV which on reaction with acetone was converted into the 1,3-dioxolane derivative VI. Reaction of compound VI with 1,3-diaminopropane, followed by acid hydrolysis, gave 9-(RS)-(2,3-dihydroxypropyl)-8-(3-aminopropylamino)adenine (VIII). Compound IV reacts with 1,3-diaminopropane under formation of a mixture of compound VIII and isomeric 9-(RS)-[3(2)-(3-aminopropylamino)-2(3)-hydroxypropyl]-8-hydroxyadenines (IX, X). 9-(RS)-(2,3-Dihydroxypropyl)-8-hydroxyadenine (XVII) was prepared by reaction of compound VI with sodium benzoxide in dimethylformamide and subsequent acid hydrolysis. Its tosylation, followed by reaction of the obtained 3'-O-p-toluenesulfonyl derivative XVIII with 1,3-diaminopropane, furnished also the compound IX. In an analogous way, 9-(RS)-[3-(3-aminopropylamino)-2-hydroxypropyl]adenine (XXI) was prepared from 3'-O-p-toluenesulfonyl derivative of compound III (XX).

The synthesis and the pharmacological properties of enantiomeric derivatives of 7-(2,3-dihydroxypropyl)theophylline

1979 ◽  
Vol 44 (8) ◽  
pp. 2550-2555 ◽  
Author(s):  
Antonín Holý ◽  
Miroslav Vaněček
Keyword(s):  
Guinea Pig ◽  
Acid Hydrolysis ◽  
Sodium Salt ◽  
Blood Circulation ◽  
Pharmacological Properties ◽  
Camp Phosphodiesterase ◽  
Derivatives Of ◽  
Subsequent Acid

7-(S)-(2,3-Dihydroxypropyl)theophylline ((S)-I) and its enantiomer (R)-I were prepared by heating of the sodium salt of theophylline with 1-O-toluenesulfonyl-2,3-O-isopropylidene-D-glycerol or its L-enantiomer and subsequent acid hydrolysis. The two enantiomers I do not differ either by the inhibition of 3',5'-cAMP-phosphodiesterase, vasodilatatory activity on isolated guinea-pig aorta, or the effect on blood circulation of dogs in vivo.

Synthesis and Biological Effects of 9-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Deazapurine Bases

1993 ◽  
Vol 58 (6) ◽  
pp. 1403-1418 ◽  
Author(s):  
Hana Dvořáková ◽  
Antonín Holý ◽  
Petr Alexander
Keyword(s):  
Acid Hydrolysis ◽  
Sodium Methoxide ◽  
Potent Inhibitor ◽  
Biological Effects ◽  
Side Chain ◽  
Cesium Carbonate ◽  
Phosphonic Acids ◽  
Dna Viruses ◽  
Derivatives Of ◽  
Subsequent Acid

Analogs of antiviral 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine (HPMPA, I), containing modified purine bases 3-deazaadenine XII, 1-deazaadenine XIV, 7-deaz-7-cyanoaadenine XXXII and 3-deazaguanine XXXVIII, were prepared by alkylation of the bases with synthon XVII, containing preformed structure of the side chain, in the presence of cesium carbonate. The obtained protected derivatives were deblocked successively with sodium methoxide and bromotrimethylsilane to give phosphonic acids XII, XIV, XXXII and XXXVIII. Compounds XII, XIV and XVI were also prepared from (S)- or (R)-9-(2,3-dihydroxypropylderivatives VI, VII and XV by the reaction with chloromethanephosphonyl dichloride, isomerization of the arising 2'- and 3'-chloromethanephosphonates and conversion of the 3'-isomers into the phosphonic acids in alkaline medium. The 3-deaza analog XII was also prepared by ditritylation of VI, reaction with bis(2-propyl) tosyloxymethanephosphonate (XXII), subsequent acid hydrolysis and reaction with bromotrimethylsilane. 3-DeazaHPMPA (XII) is a potent inhibitor of DNA viruses (HSV-1, HSV-2, VZV, CMV) and exhibits activity against Plasmodium sp.

Preparation of enantiomeric and racemic 2,3,4,5-tetrahydroxypentyl derivatives of adenine, cytosine and uracil

1982 ◽  
Vol 47 (10) ◽  
pp. 2786-2805 ◽  
Author(s):  
Antonín Holý
Keyword(s):  
Acid Hydrolysis ◽  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Protecting Groups ◽  
Sodium Salts ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Subsequent Acid

1-(Adenin-9-yl)-1-deoxy-DL-ribitol (III), -D-arabitol (IXa), -L-arabitol (XIVa), -DL-xylitol (XXIVa), 1-(cytosin-L-yl)-1-deoxy-D-arabitol (IXb), -L-arabitol (XIVb), 1-(uracil-1-yl)-1-deoxy-D-arabitol (IXc), -L-arabitol (XIVc) and -DL-xylitol (XXIVb) were prepared by reaction of 1-O-p-toluenesulfonyl-2,3:4,5-di-O-isopropylidenealditols Ib, VIIb, XIIb and XXIIb with sodium salts of adenine, N4-benzoylcytosine or 4-methoxy-2-pyrimidone followed by removal of the protecting groups. Condensation of the mentioned sodium salts with methyl 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-β-D-ribofuranoside (IV) with subsequent acid hydrolysis and reduction with sodium borohydride afforded 1-(adenin-9-yl)-1-deoxy-L-ribitol (VIa) and 1-(cytosin-1-yl)-1-deoxy-L-ribitol (VIb). 1-(Adenin-9-yl)-1-deoxy-L-lyxitol (XVII), -L-lyxitol (XVIII) and -2-O-methyl-D-lyxitol (XXI) were prepared analogously. Acid hydrolysis of 5-(adenin-9-yl)-5-deoxy-4-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (XXVa), followed by reduction with sodium borohydride and catalytic hydrogenation, gave 1-(adenin-9-yl)-1-deoxy-L-xylitol (XXVIb).

ÉTUDES SUR LA SYNTHÈSE DE L’HYDROXYPROLINE À PARTIR DE DÉRIVÉS DE L’ACIDE 2-AMINO-4-PENTÈNOÏQUE

1956 ◽  
Vol 34 (4) ◽  
pp. 502-514 ◽  
Author(s):  
Roger Gaudry ◽  
Louis Berlinguet ◽  
André Langis ◽  
Gérard Paris
Keyword(s):  
Double Bond ◽  
Acid Hydrolysis ◽  
Malonic Acid ◽  
Systematic Investigation ◽  
Carboxyl Group ◽  
Reaction Products ◽  
Pentanoic Acid ◽  
Copper Salts ◽  
Halogenation Reaction ◽  
Derivatives Of

A systematic investigation of the synthesis of 4-hydroxy-DL-proline and 2-amino-4-dihydroxyvaleric acid has been made, starting from the following derivatives of 2-amino-4-pentenoic acid: ethyl allylacetamidomalonate, ethyl allylacetamidocyanoacetate, 2-phthalimidopentenoic acid, allylacetamido-malonic acid, acetylallylglycine, 5-allylhydantoin, and 3-phenyl-5-allylhydantoin. Chlorine or bromine was added to the double bond of these compounds, and the reaction products were either derivatives of 5-halogenated-4-valerolactones or derivatives of 4,5-dihalogenated pentanoic acids, depending on whether the carboxyl group of the pentanoic acid was free or not when the halogenation reaction was carried out. Acid hydrolysis followed by treatment with barium hydroxide always gave mixtures, in different ratio, of 4-hydroxy-DL-proline and 2-amino-4,5-dihydroxyvaleric acid which were analyzed and isolated as the copper salts. In the case of 5-(2,3-dibromopropyl)hydantoin and 3-phenyl-5-(2,3-dibromopropyl)hydantoin, no cyclization could be obtained.

SYNTHÈSES D'ACIDES AMINOBUTYRIQUES: II. ACIDES ALKYLAMINO-2 HYDROXY-4 BUTYRIQUES

1962 ◽  
Vol 40 (10) ◽  
pp. 1960-1964 ◽  
Author(s):  
Réal Laliberté ◽  
Louis Berlinguet
Keyword(s):  
Acid Hydrolysis ◽  
Primary Amines ◽  
Hydroxybutyric Acid ◽  
Derivatives Of

Starting from 2-bromo-4-butyrolactone which was treated with primary amines, five new 2-alkylamino-4-hydroxy-N-alkylbutyramides were obtained in good yields. Acid hydrolysis gave the corresponding lactones, which, when treated with Ba(OH)2, gave the 2-alkylamino-4-hydroxybutyric acids. The new derivatives of homoserine thus prepared are: 2-methylamino-4-hydroxybutyric acid, 2-ethylamino-4-hydroxybutyric acid, 2-propylamino-4-hydroxybutyric acid, 2-butylamino-4-hydroxybutyric acid, and 2-cyclohexylamino-4-hydroxybutyric acid.Some of these amides were easily lactonized in HCl-acetone medium. Two 2-alkylamino-4-chloro-N-alkylbutyramides were also prepared.

Phytol And Glycerol Derivatives From The Marine Green Alga Codium Iyengarii Of The Karachi Coast (Arabian Sea)

2001 ◽  
Vol 56 (8) ◽  
pp. 837-841 ◽  
Author(s):  
Muhammad Shaiq Ali ◽  
Muhammad Saleem ◽  
Viqar Uddin Ahmad ◽  
Simin Shameel
Keyword(s):  
Ethyl Acetate ◽  
Acid Hydrolysis ◽  
Green Alga ◽  
Arabian Sea ◽  
Methanolic Extract ◽  
Derivatives Of ◽  
Soluble Part ◽  
Marine Green Alga

The ethyl acetate soluble part of a methanolic extract of the marine green alga Codium iyengarii, collected from the Karachi coast of the Arabian Sea, afforded four new derivatives of glycerol named : codioside A,B,C,D (1-4), a new derivative of frans-phytol named codioester (5) and rrans-phytol (6). The structures of 1 -5 were elucidated with the aid of acid hydrolysis, methylation, GC-MS, and spectroscopy. The structure of 1 was confirmed through the HMBC NMR technique and the structures of compounds 2 -4 were based on the assignments made for 1

1'-Derivatives of sucrose and their acid hydrolysis

1980 ◽  
Vol 33 (11) ◽  
pp. 2487 ◽  
Author(s):  
RD Guthrie ◽  
ID Jenkins ◽  
JJ Watters
Keyword(s):  
Acid Hydrolysis ◽  
Hydrolysis Of ◽  
Derivatives Of

Syntheses of 1'-chloro-1'-deoxy- and 1'-deoxy-sucrose are described. Several routes were investigated, the most successful being through 6,1',6'-tri-O-(2,4,6-trimethylbenzenesulfonyl)sucrose. Attempts to prepare 1'-deoxy-1'-fluorosucrose were unsuccessful. The rates of the acid-catalysed hydrolysis of 1'-chloro-1'-deoxysucrose and of 1'- deoxysucrose have been measured. These values are compared with that for sucrose itself. The mechanism of the hydrolyses is discussed.

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