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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of 3′-Azido, 2′,3′-Didehydro, and 3′,4′-Didehydro Nucleosides from 5-Alkoxymethyluracils (1998)
    Springer
    Monatshefte für Chemie 129 (1998), S. 99-109 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. Nucleosides ; convergent synthesis of; Nucleosides ; 3′-azido-2′-deoxy; Nucleosides ; 2′ ; 3′-didehydro; Nucleosides ; 3′ ; 4′-didehydro; 5-Alkoxymethyluracil nucleosides; Human immunodeficiency virus; Herpes simplex virus.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung.  Reaktion von Methyl-5-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranosid (3) mit den silylierten 5-Alkoxymethyluracilen 2a–c unter Verwendung von Trimethylsilyltrifluormethansulfonat als Katalysator ergab die α-Nucleoside 4a–c und die β-Nucleoside 5a–c. Die entsprechenden 3′,4′- und 4′,5′-Didehydronucleoside 6–9 wurden durch Behandeln der Jodnucleoside 4a–c oder 5a–c mit 10 Äquivalenten Natriummethoxid in siedendem Methanol über eine Eliminierungsreaktion hergestell. Die entschützten 3′-Azidonucleoside 10a–c und 11a–c vom AZT-Typ wurden ebenso wie die 4′,5′-Didehydronucleoside 7a–c und 9a–c durch Umsetzung von 4a–c und 5a–c mit Natriumazid und nachfolgender Behandlung mit Tetrabutylammoniumfluorid erhalten.
    Notes: Summary.  Reaction of methyl 5-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside (3) with silylated 5-alkoxymethyluracils 2a–c using trimethylsilyl trifluoromethanesulfonate as a catalyst afforded the α nucleosides 4a–c and the β nucleosides 5a–c. The corresponding 3′,4′- and 4′,5′-didehydro nucleosides 6–9 were prepared in an elimination reaction by treating the iodo nucleosides 4a–c or 5a–c with 10 equivalents of sodium methoxide in methanol under reflux. The deprotected 3′-azido nucleosides 10a–c and 11a–c of the AZT type as well as the 4′,5′-didehydro nucleosides 7a–c and 9a–c were prepared by treating 4a–c and 5a–c, respectively, with sodium azide and subsequently with tetrabutylammonium fluoride.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00010110
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of Triazenopyrazole Derivativesas Potential Inhibitors of HIV-1 (1999)
    Springer
    Monatshefte für Chemie 130 (1999), S. 1167-1173 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. Triazenopyrazoles; Nucleosides ; convergent synthesis of; Nucleosides ; 1-(5-triazeno)pyrazole; Nucleosides ; 2-(5-triazeno)pyrazole; Human immunodeficiency virus; Herpes simplex virus.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung.  Ethoxymethylenmalonitril und Bis(methlthio)methylenmalonitril wurden mit Hydrazinhydrat zu 5-Aminopyrazol-4-carbonitril (3a) und 5-Amino-3-methyltiopyrazol-4-carbonitril (3b) umgesetzt. Behandlung mit salpetriger Säure und Kupplung mit verschiedenen sekundären Aminen ergab die Triazenopyrazole 4a–j. 5-(3,3-Diethyl-1-triazeno)pyrazol-4-carbonitril (4c) wurde in seine beiden regioisomeren 2-Deoxyribonucleoside 5a,bübergeführt, welche anschließend mit H2O2/OH− zu den entsprechenden Carboxamiden 6a,b hydrolysiert wurden. Alle hergestellten Verbindungen wurden auf ihre biologische Aktivität gegenüber HIV-1 und Herpes simplex getestet. Nur 4c zeigte geringfügige Aktivität gegenüber HIV-1 (ED 50=32μM).
    Notes: Summary.  Ethoxymethylenemalononitrile and bis(methylthio)methylenemalononitrile were condensed with hydrazine hydrate to yield 5-aminopyrazole-4-carbonitrile (3a) and 5-amino-3-methylthiopyrazole-4-carbonitrile (3b), respectively. These compounds were treated with nitrous acid and coupled with different secondary amines to yield the triazenopyrazoles 4a–j. 5-(3,3-Diethyl-1-triazeno)pyrazole-4-carbonitrile (4c) was transferred into its two regioisomeric 2-deoxyribose nucleosides 5a,b which were subsequently hydrolyzed with H2O2/OH− to give the corresponding carboxamides 6a,b. All synthesized compounds were tested for biological activity against HIV-1 and herpes simplex virus, but only 4c showed moderate activity against HIV-1 with ED 50=32μM.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00010295
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis and antiviral evaluation of quinazoline, thieno-[2,3-d]pyrimidine, and lumazine analogues of 3′-fluoro-3′-deoxythymidine (FLT) (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1371-1375 
    Details
    ISSN: 0947-3440
    Keywords: Nucleosides ; HIV ; 3′-Fluoronucleosides ; FLT analogues ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,4(1H,3H)-Quinazolinediones 3a-c, lumazine (3d) and thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (8) were silylated and condensed with methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (2) by using trimethylsilyl triflate as a catalyst to afford the corresponding cyclic nucleosides 4 and 9 and acyclic nucleosides 5 and 10. Removal of the protecting group from the glycon moiety was achieved in good yields by treatment with sodium methoxide in methanol at room temperature. The new FLT analogues were devoid of activity against HIV-1 and HSV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507183
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  • 4
    Electronic Resource
    Electronic Resource
    Anomalously Coupled Nucleosides, II. Reaction of 3-[N6-(4-Chlorophenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranose with Alcohols and Anilines (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 705-708 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ungewöhnlich verknüpfte Nucleoside, II. - Reaktion von 3-[N6-(4-Chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranose mit Alkoholen und Anilinen3-[N6-(4-Chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranose (1) wurde in die Alkyl-3-[N6-(4-chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranoside 2 und die N-Aryl-3-[N6-(4-chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranosylamine 4 umgewandelt. Die Verbindungen 2 wurden als α/β-Anomeren-Gemische isoliert, bei verlängerten Reaktionszeiten wurden jedoch reine α-Anomere 3 erhalten.
    Notes: 3-[N6-(4-Chlorphenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranose (1) has been converted into the alkyl 3-[N6-(4-chlorophenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranosides 2 and into the N-aryl-3-[N6-(4-chlorophenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranosylamines 4. The compounds 2 were isolated as mixtures of α and β anomers whereas pure α anomers 3 could be obtained after prolonged reaction times.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870812
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  • 5
    Electronic Resource
    Electronic Resource
    Anomalously Coupled Nucleosides, III. Coupling of Unprotected 2-Deoxy-D-ribose at C-3 with N6-Acyladenines as a New Route to Isomers of Adenosine (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 787-791 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ungewöhnlich verknüpfte Nucleoside, III. - Verknüpfung von ungeschützter 2-Desoxy-D-ribose an C-3 mit N6-Acyladeninen, ein neuer Weg zu Isomeren des AdenosinsDie ungewöhnliche Verknüpfung von N6-Acyladeninen 1 mit C-3 von ungeschützter 2-Desoxy-D-ribose (2) gelingt mit P4O10/H2O/Bu3N als Kupplungsreagens in Chloroform. Von den so erhaltenen 3-(9-Adenyl)-2,3-didesoxy-D-threo-pentopyranosen 3 wurden mit Ammoniak in Methanol die Acylgruppen unter Bildung des ungewöhnlich verknüpften Isomers 5 von Adenosin abgespalten.
    Notes: Anomalous coupling at C-3 of unprotected 2-deoxy-D-ribose (2) with N6-acyladenosines 1 was performed using P4O10/H2O/Bu3N in chloroform as the coupling reagent. The 3-(9-adenyl)-2,3-dideoxy-D-threo-pentopyranoses 3 formed were deprotected with ammonia in methanol to give the anomalously coupled isomer 5 of adenosine.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870829
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  • 6
    Electronic Resource
    Electronic Resource
    A new route to 2′,3′-dideoxycytidine (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 599-602 
    Details
    ISSN: 0170-2041
    Keywords: Glycosidation ; 4-Biphenylcarbonyl protecting group ; Barton deoxygenation ; 2′,3′-Dideoxycytidine ; Nucleosides, 2′,3′-dideoxy- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Deoxy-D-ribose (1) was converted into its methyl glycofuranoside 2, which was treated with 4-biphenylcarbonyl chloride to give a separable mixture of 3 (26%) and 4 (40%). Compounds 3 and 4 were deoxygenated by Barton deoxygenation to give the corresponding 2,3-dideoxyribose derivatives 7 and 8 in good yields as crystalline materials. Reaction of 7 and 8 with the silylated N4-isobutyrylcytosine 9, using trimethylsilyl triflate as catalyst afforded a separable mixture of the protected 2′,3′-dideoxynucleosides 10 (29%) and 11 (31%) which were deprotected with methanolic ammonia to give 2′,3′-dideoxycytidine (12) and its α-anomer 13.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001110
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  • 7
    Electronic Resource
    Electronic Resource
    Phosphorus pentoxide in organic synthesis, VII. Synthesis of 3-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-imines (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 2066-2072 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Phosphorpentoxid in der Organischen Synthese, VII. - Synthese von 3-Aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-iminenDurch Umsetzung von 2-(Acetylamino)-3-pyrrolcarbonitrilen 1 mit einer Mischung von Phosphorpentoxid, N,N-Dimethylcyclohexanamin und einem geeigneten Arylamin-hydrochlorid bei 150-180 °C werden die Titelverbindungen 2 erhalten. Das verwendete Arylamin-hydrochlorid muß absolut wasserfrei sein, da anderenfalls 4-(Arylamino)pyrrolo[2,3-d]pyrimidine 4 als Nebenprodukte entstehen können. - Die Ergebnisse der Prüfung auf Pestizid- und Antikrebs-Wirksamkeit werden mitgeteilt.
    Notes: The title compounds 2 were prepared by treating 2-(acetylamino)-3-pyrrolecarbonitriles 1 with a mixture of phosphorus pentoxide, N,N-dimethylcyclohexanamine, and an appropriate arylamine hydrochloride at 150-180°C. The importance of using absolutely anhydrous arylamine hydrochlorides is stressed because failing this, 4-(arylamino)pyrrolo[2,3-d]pyrimidines 4 can be formed as by-products. - The results from pesticide and anticancer screenings are reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319831203
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  • 8
    Electronic Resource
    Electronic Resource
    Phosphorus Pentoxide in Organic Synthesis, XXIX. Synthesis of 4-Arylamino-5,6,7,8-Tetrahydro-1H-Pyrazolo[3,4-b]Quinolines and the Corresponding N-Mannich Bases (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1728-1735 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Phosphorpentoxid in der Organischen Synthese, XXIX. - Synthese von 4-Arylamino-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b]chinolinen und entsprechenden N-Mannich-Basen4-Arylamino-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b]chinoline 2 lassen sich aus 5-Amino-1H-pyrazol-4-carbonsäure-ethylester (1) und Cyclohexanon durch Erhitzen in einer Mischung aus P4O10, N,N-Dimethylcyclohexylamin und einem geeigneten Arylamin-hydrochlorid herstellen (8 - 52% Ausbeute). Umsetzung von 2 mit Formaldehyd und sekundären Aminen ergibt die Mannich-Basen 3 zu 45 - 94%. Versuche, die Verbindungen 2 in den Positionen 5,6,7 und 8 nach einer früher benutzten Methode zu dehydrieren, scheiterten.
    Notes: 4-Arylamino-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b]quinolines 2 have been synthesized from ethyl 5-amino-1H-pyrazole-4-carboxylate (1) and cyclohexanone by heating in a reagent mixture of P4O10, N,N-dimethylcyclohexylamine, and an appropriate arylamine hydrochloride (8 - 52% yield). Reaction of 2 with formaldehyde and secondary amines afforded the Mannich bases 3 in 45 - 94% yield. Attempts to prepare the 5,6,7,8-dehydrogenated analogues of 2 using a previously adopted method failed.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619861006
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  • 9
    Electronic Resource
    Electronic Resource
    Coupling of Unprotected 2-Deoxy-D-ribose at C-3 as a New Route to 2,3-Dideoxy-3-phthalimido-D-pentoses (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 1111-1114 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Direct condensation of 2-deoxy-D-ribose (2) with phthalimides using P4O10/H2O/Bu3N reagent in chloroform at 40°C results in a coupling at C-3 of the carbohydrate moiety to give an isomeric mixture of 2,3-dideoxy-3-phthalimido-D-pentoses 3-5. Acetylation of 3b-5b using acetic anhydride in dry pyridine gives the corresponding acetylated derivatives 6-8. After treating the mixture of 3b, 4b, and 5b with triphenylmethyl chloride in pyridine, pure threo-pyranose derivative 3b and pure tritylated erythro-furanose derivative 9 are obtained by fractional precipitation.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870881
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis of 2′,5′-Dideoxyuridine-5′-phosphonates (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 127-129 
    Details
    ISSN: 0170-2041
    Keywords: Uridine-5′-phosphonates, 2′,5′-dideoxy- ; D-erythro-Pentofuranose-5-phosphonates, 2,5-dideoxy- ; Arbuzov reaction ; Human immunodeficiency virus ; Herpes simplex virus ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Methyl 2,5-dideoxy-5-iodo-3-O-pivaloyl-D-erythro-pentofur-anoside (5) was synthesized from 2-deoxy-D-ribose and treated with triethyl phosphite to give the phosphonate 6. Reaction of 6 with silylated 2,4-dihydroxypyrimidine 7 in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst afforded nucleoside phosphonates 8 and 9 which were deprotected with C2H5ONa in ethanol to give the diethyl 2′,5′-dideoxyuridine-5′-phosphonate 10 and its α-anomer 11. No activity was found for the nucleosides 8-11 against HIV or HSV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920124
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