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  • Organic Chemistry  (24)
  • 2-(5-triazeno)pyrazole; Human immunodeficiency virus; Herpes simplex virus.  (1)
  • 2-Thiohydantoin  (1)
  • 1
    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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  • 2
    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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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of New 2-Azaadenines and 2-Azahypoxanthines from 4-Diazo-4H-imidazoles (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1012-1020 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese neuer 2-Azaadenine und 2-Azahypoxanthine aus 4-Diazo-4H-imidazolenEine Reihe neuer, möglicherweise biologisch wirksamer N6-substituierter 2-Azaadenine 5 wurde aus 5-Amino-1H-imidazol-4-carboxamid-hydrochlorid über 4-Diazo-4H-imidazol-5-carbonitril (1), das mit primären Aminen gekuppelt wurde, mit 11 - 78proz. Ausbeute hergestellt. Auch einige 1-substituierte 2-Azahypoxanthine 9 wurden aus 5-Amino-1H-imidazol-4-carbonsäure-ethylester (6) über 4-Diazo-4H-imidazol-5-carbonsäure-ethylester (7) durch Kopplung mit primären Aminen mit 17 - 66proz. Ausbeute gewonnen.
    Notes: 5-Amino-1H-imidazole-4-carboxamide hydrochloride has been converted into a series of new, potentially biologically active N6-substituted 2-azaadenines 5 via 4-diazo-4H-imidazole-5-carbonitrile (1) which was coupled with primary amines to give 5 in 11 - 78% yield. Further, some 1-substituted 2-azahypoxanthines 9 have been prepared in 17 - 66% yield from ethyl 5-amino-1H-imidazole-4-carboxylate (6) via ethyl 4-diazo-4H-imidazole-5-carboxylate (7) which was coupled with primary amines.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860606
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  • 5
    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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  • 6
    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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  • 7
    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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  • 8
    Electronic Resource
    Electronic Resource
    Nitriles in Heterocyclic Synthesis: A Novel Synthesis of 2-Amino-3-pyrrolecarbonitriles (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1145-1146 
    Details
    ISSN: 0170-2041
    Keywords: 3-Pyrrolecarbonitriles, 2-amino- ; Malononitriles, phenylacyl ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Amino-3-pyrrolecarbonitriles are prepared by the reaction of phenacylmalononitrile with primary aromatic amines using a catalytical amount of concd. HCl.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890285
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis of 6-dimethylaminopurine 2′,3′-dideoxynucleosides (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 879-883 
    Details
    ISSN: 0170-2041
    Keywords: Nucleosides, convergent synthesis ; Nucleosides, 2′,3′-dideoxy- ; Nucleosides, 2′,3′-didehydro- ; Adenine, N6N6-dimethylnucleosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The trimethylsilyated 6-dimethylaminopurine 1 was coupled with the 2′,3′-dideoxyribose derivatives 2a, b and 7 by using trimethylsilyl triflate as catalyst to yield the corresponding nucleosides 3a, b, 4a, b and 8, which were appropriately deprotected to give the desired nucleosides 5a, b and 9 as well as the related α-isomers 6a, b and 10. The 2-deoxyribose derivative 12 was mesylated at the 3′-O-position to give 13 which was coupled similarly with 1 to yield compound 14 and its α-anomer 15. Compounds 14 and 15 were treated with tetrabutylammonium fluoride to give the desired 2′,3′-didehydro-2′,3′-dideoxynucleoside analogue 16 and its α-anomer 17.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101152
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  • 10
    Electronic Resource
    Electronic Resource
    Phosphoramides, XV. Phosphorus pentoxide amine mixtures as reagents in the synthesis of 2-(dialkylamino)quinolines (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1485-1491 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Phosphoramide, XV1).  -  Phosphorpentoxid/Amin-Gemische als Synthesereagenzien für 2-(Dialkylamino)chinolineBei der Umsetzung von Acetaniliden und N,N-Dialkylformamiden mit einer Mischung aus Phosphorpentoxid und einem Dialkylamin bei 250°C wurden 2-(Dialkylamino)chinoline erhalten. Es wird ein HMPT-induzierten Ringschlußreaktionen verwandter Mechanismus vorgeschlagen. Das jeweilige Amin und Formamid müssen aufeinander abgestimmt sein, weil Transacylierungen stattfinden. Die glatteste Reaktion wird beobachtet, wenn das eingesetzte Amin und dasjenige, das aus dem Formamid freigesetzt werden kann, gleich sind, oder wenn das erstere die größere Nucleophilie besitzt. Der Ringschluß kann durch sterische Effekte gehindert werden. Anstelle der Formamide können auch Formate eingesetzt werden.
    Notes: 2-(Dialkylamino)quinolines were prepared by treating acetanilides and N,N-dialkylformamides with a mixture of phosphorus pentoxide and a dialkylamine at 250°C. A mechanism which is related to HMPT induced ring closure reactions is proposed. Proper choice of amine and formamide is important, because transacylation reactions take place. The cleanest reaction was obtained if the amine used and the amine, which could be liberated from the formamide, were identical, or if the former amine has the greater nucleophilicity. Sterical hindrance in the ring closing step may occur. Formates, instead of formamides, can also be used.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810820
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