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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of novel HMG-CoA reductase inhibitors, II. Heterocyclic analogs of mevinolin (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1877-1883 
    Details
    ISSN: 0947-3440
    Keywords: HMG-CoA reductase inhibitors ; 3-Indolylheptanoates and -acetates ; 4-Chromanylheptanoates and -acetates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The indole (1) and chroman analogs (2) of mevinolin and their 6S diastereomers 15c and 25d were synthesized in several steps starting with methyl (R)-3-[(tert-butyldimethylsilyl)oxy]-4-formylbutyrate (12) and 2-(indol-3-yl)ethanol (3) or 6-methoxychroman-4-one (16), respectively. Compounds 1 and 2 inhibited moderately the HMG-CoA reductase. The diastereomers 15c and 25d were shown to be inactive.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199510263
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  • 2
    Electronic Resource
    Electronic Resource
    Beiträge zur titrimetrischen Bestimmung von dimeren Hydroxyaldehyden (1975)
    Springer
    Fresenius' Zeitschrift für analytische Chemie 276 (1975), S. 201-204 
    Details
    ISSN: 1618-2650
    Keywords: Best. von Glykolaldehyd, Glycerinaldehyd, Hydroxyaldehyden ; Volumetrie ; Dimere
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Es wurden die Möglichkeiten für die titrimetrische Bestimmung von dimerem Glykolaldehyd (Fp: 94–96° C) und dl-Glycerinaldehyd (Fp: 138–141° C) untersucht. Die systematischen Fehler der auf Grund verschiedener funktioneller Gruppen durchführbaren Messungen sind von der Stabilität ihrer cyclischen Halbacetale sowie von den ihrer Depolymerisation folgenden weiteren Gleichgewichten bestimmt. Das aus dem dl-Glycerinaldehyd gebildete Halbacetal besitzt höhere Stabilität als dasjenige aus dem Glykolaldehyd. Mit der Hydrogensulfit-Methode werden 95–96%, mit der Hydroxylamin-Methode dagegen 98–99% vom wahren Wert gefunden. In Wasser gelöst zersetzt sich der Glykolaldehyd verhältnismäßig rasch, und das Gleichgewicht kann durch beide Aldehydreaktionen quantitativ gegen die Monomerenform verschoben werden. Unsere Untersuchungen ergaben, daß die Hydroxylamin-Methode zur Bestimmung der in Form cyclischer Halbacetale kristallisierenden, dimeren Hydroxyaldehyde Vorteile gegenüber der Hydrogensulfit-Methode bietet.
    Notes: Abstract Possibilities for the titrimetric determination of dimeric glycolaldehyde (m.p. 94–96° C) and dl-glyceraldehyde (m.p. 138–141° C) have been investigated. The systematic errors based on different functional groups depend on the stability of the cyclic semiacetals and on the subsequent equilibria established after their depolimerisation. The semiacetal of dl-glyceraldehyde is more stable than that of glycolaldehyde. 95–96% and 98–99% of the real content were found by the hydrogensulphite and hydroxylamine methods, respectively. Glycolaldehyde decomposes rather quickly in aqueous solution and the equilibrium can be shifted towards the monomeric form by both the aldehyde reactions. The hydroxylamine method proved to be more advantageous for the determination of the dimeric hydroxyaldehydes, which cristallise in the form of cyclic semiacetals.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00437567
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  • 3
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie von 1,2,4-Oxadiazolen mit C-5-Heteroatom-Bindung, II. Synthese von 5,6-Dihydro-4H-1,2,4-oxadiazinen durch Ringerweiterung von Δ2-1,2,4-Oxadiazolin-5-onen (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 1911-1923 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1,2,4-Oxadiazoles containing a C-5-heteroatom Bond, II Synthesis of 5,6-Dihydro-4H-1,2,4-Oxadiazines by ring Extention of Δ2-1,2,4-oxadiazolin-5-onesN-(2-Hydroxyalkyl)-, and N-(3-chloro-2-hydroxypropyl)-Δ2-1,2,4-oxadiazolin-5-one derivatives (6, 8), prepared by reaction of Δ2-1,2,4-oxadiazolin-5-ones (4) with alkylene oxides or epichlorohydrine, respectively, are used as starting materials for the synthesis of 5,6-dihydro-4H-1,2,4-oxadiazines (2) as well as for that of N-monosubstituted amidoximes (7, 11). The reactivity of 2 with methyl iodide and acylating agents is reported.
    Notes: Die durch Reaktion der Δ2-1,2,4-Oxadiazolin-5-one 4 mit Epoxiden bzw. Epichlorhydrin hergestellten N-(2-Hydroxyalkyl)- bzw. N-(3-Chlor-2-hydroxypropyl)-Derivate 6, 8 werden bei der Synthese von 5,6-Dihydro-4H-1,2,4-oxadiazinen (2) bzw. der N-monosubstituierten Amidoxime 7, 11 als Ausgangsmaterialien eingesetzt. Die Reaktionsfähigkeit von 2 gegenüber Methyljodid und Acylierungsmitteln wird beschrieben.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080614
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese von 4-Aminopyrimidinen aus 1,2,4-Oxadiazolen, I. Eine neue, allgemeine Methode zur Herstellung von 4-Aminochinazolinen und deren Heteroanaloga (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3183-3193 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, I. A Novel General Method for the Preparation of 4-Aminoquinazolines and their Hetero AnaloguesCatalytic hydrogenation of 3-(2-aminoaryl)-1,2,4-oxadiazoles (9, 12, 15, 18, 21) to 2-amino-N-acylarenecarboxamidines (10, 13, 16, 19, 22) followed by dehydration gave condensed 4-aminopyrimidines (11, 14, 17, 20, 23), while the corresponding secondary amines (24) afforded 1,2-disubstituted 4-iminoquinazolines (26). Reduction and dehydration of 3-[2-(acylamino)phenyl]-1,2,4-oxadiazoles (28) provided, via a somewhat different pathway, 4-(acylamino)quinazolines (31).
    Notes: Katalytische Hydrierung von 3-(2-Aminoaryl)-1,2,4-oxadiazolen (9, 12, 15, 18, 21) zu 2-Amino-N-acylarencarboxamidinen (10, 13, 16, 19, 22) und nachfolgende Dehydratisierung ergab kondensierte 4-Aminopyrimidine (11, 14, 17, 20, 23), während die entsprechenden sekundären Amine (24) zu 1,2-disubstituierten 4-Iminochinazolinen (26) führten. Reduktion und Dehydratisierung der 3-[2-(Acylamino)phenyl]-1,2,4-oxadiazole 28 lieferte auf einem von dem vorangehenden teilweise verschiedenen Reaktionsweg die 4-(Acylamino)chinazoline 31.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171104
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  • 5
    Electronic Resource
    Electronic Resource
    Untersuchungen über Verbindungen mit Berban-Gerüst, IV. Über die Herstellung von halogenierten Despyrroloyohimbon-Derivaten mit prostaglandinartiger und prostaglandin-antagonistischer Wirkung (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3390-3403 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigation on the Chemistry of Berbans, IVSynthesis of Halogen Containing Depyrroloyohimbon Derivatives with PG-like and PG-antagonistic EffectHalogenation of depyrroloyohimbon derivatives of different configurations (1a-d, 2a-c, 3a-c) was investigated in order to obtain useful intermediates for the synthesis of depyrroloreserpines. The isomerisation of the primer products (9a-e, 10b and 11a, c, e) to γ-bromo derivatives (9f-j, 10g and 11f, h, j) was also studied.
    Notes: Die Halogenierung von Despyrroloyohimbon-Derivaten verschiedener Konfiguration (1a-d, 2a-c, 3a-c) wurde untersucht, um brauchbare Intermediärprodukte zur Synthese von Despyrroloreserpinen zu gewinnen. Die Isomerisierung von Primärprodukten (9a-e, 10b und 11a, c, e) zu γ-Brom-Derivaten (9f-j, 10g und 11f, h, j) wurde studiert.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761091017
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis of Novel HMG-CoA Reductase Inhibitors, I. Naphthalene Analogs of Mevinolin (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 145-157 
    Details
    ISSN: 0170-2041
    Keywords: HMG-CoA reductase inhibitors ; Naphthylacetates ; Pig liver esterase ; Glutarate, 3-hydroxy ; Lactones ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title compounds 2 and their corresponding (6 S) epimers 18 are prepared in several steps by starting with chiral formyl ester 5, and α-tetralones 10: (1) coupling reaction with the ylide generated from 11 to yield unsaturated ester 13, (2) reduction to the corresponding alcohol 14, (3) addition of the Grignard reagent derived from 14 to formyl ester 5 to afford the hydroxy esters 16 and 17, and (4) lactonization. This procedure is also used to synthesize the β-naphthyl analogs 29 and 30. Some results obtained from HMG-CoA reductase inhibitor screening are also reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920127
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Reserpine-type Alkaloids, II. Synthesis of 18-Hydroxyyohimbine Stereoisomers and Raunescine Analogues with Normal Skeletons (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1278-1291 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese von Alkaloiden des Reserpin-Typs, II. - Synthese von 18-Hydroxyyohimbin-Stereoisomeren und Raunescin-Derivaten mit normalem MolekülgerüstAusgehend von dem in der vorausgehenden Mitteilung beschriebenen Ketoester 2 wurden drei Raunescin-Derivate (7c, 9c, 10c) und ein Isoraunescin-Stereoisomer (10d) - alle mit normalem Yohimbangerüst - synthetisiert.
    Notes: Starting from the previously described keto ester 2, three raunescine analogues (7c, 9c, 10c) and one isoraunescine stereoisomer (10d) - all with a normal yohimbane skeleton - have been synthesized.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830803
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  • 8
    Electronic Resource
    Electronic Resource
    Total Synthesis of Two Naturally Occurring Neolignans of Potential Biological Activity (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 593-594 
    Details
    ISSN: 0170-2041
    Keywords: Neolignans ; Balanophonin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of the racemates of two naturally occurring neolignans, 1 and 2, was accomplished starting from methyl ferulate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1989198901104
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, III A Novel Type of Formation of Olefins from Amines (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 111-113 
    Details
    ISSN: 0009-2940
    Keywords: Olefin formation ; Pyrimido[6,1-α]isoquinolines ; 4-Aminopyrimidines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On heating at 100°C, 1,2,3,4-tetrahydro-6,7-dialkoxy-1-[(acylamidino)methylene]isoquinolines (5) are transformed into 4-substituted 6,7-dihydro-9,10-dialkoxy-2H-pyrimido[6,1-α]isoquinoline-2-imines (6), while at 140°C they undergo a novel prototropic rearrangement via 6 to give 4-amino-6-(4,5-dialkoxy-2-vinylphenyl)-2-phenylpyrimidines (7). The structure of 7a has been determined by X-ray analysis.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240119
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  • 10
    Electronic Resource
    Electronic Resource
    Ring-Chain Tautomerism of 3,5-Disubstituted 5,6,7,8-Tetrahydro-3H-3H-[1,2,4]oxadiazolo[4,3-c]pyrimidine, a Novel Heterocyclic Ring System (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2065-2070 
    Details
    ISSN: 0009-2940
    Keywords: Ring-chain tautomerism ; 3H-[1,2,4]-Oxadiazolo[4,3-c]pyrimidine, 5,6,7,8-tetrahydro- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 3-aminopropionamide oxime (7) with two equiv. of benzaldehyde or of a substituted benzaldehyde gives cis-3,5-diaryl-5,6,7,8-tetrahydro-3H[1,2,4]oxadiazolo[4,3-c]-pyrimidines (cis-11a-c,e). According to 1H-, 13C-, and 15N-NMR studies these compounds form in solution a novel triple tautomeric equilibrium comprising cis- and trans-11a-c, e and 3-[2-(benzylidineamino)ethyl]-5-aryl-4,5-dihydro-1,2,4-oxaliazoles (10a-c, e). However, the solid obtained from 7 and two equiv. of cinnamaldehyde proved to be an imine (10g), which again formed in solution a similar triple tautomeric system analogously to the mutarotation of sugars. The structure of 11a and 10g was confirmed by X-ray crystallography.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240931
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