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  • 1
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlungen nichtsteroider Strukturen, V. Mikrobiologische Reaktionen von substituierten 1-Äthyl-4-oxo-1,4-dihydrochinolin-3-carbonsäuren (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 2636-2642 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Transformations of Nonsteroidal Structures, V. Microbiological Reactions of Substituted 1-Ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acids1-Ethyl-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1) is transformed to the methyl ester by Streptomyces surinam. Penicillium adametzi hydroxylates the substrate at the 7-methyl substituent, whereas 1 -ethyl-8-methoxy-5-methyl-4-oxo- 1,4-dihydroquinoline-3-carboxylic acid (4) is hydrolyzed to the free phenol by the same fungi. l-Ethyl-4-oxo-1,4,6,7,8,9-hexahydrobenzo[g]quinolinc-3-carboxylic acid (6) is hydroxylated in 7 - and 8-position by Penicillium adametzi, in 6- and 7- (or 8-) position by Streptomyces achromogenes and in 6-position by Sporotrichum sulfurescens. 5-Ethyl-8-oxo-2,3,5,8-tetrahydrofuro[2,3-g]quinoline-7-carboxylic acid (10) undergoes only a hydrolytic cleavage of the dihydrofuranering.
    Notes: 1-Äthyl-7-methyl-4-oxo-1,4-dihydrochinolin-3-carbonsäure (1) wird durch Streptomyces surinam in den Methylester umgewandelt. Penicillium adametzi hydroxyliert das Substrat am 7-Methylsubstituenten, während bei der 1 -Äthyl-8-methoxy-5-methyl-4-oxo- 1, 4-dihydrochinolin-3-carbonsäure (4) mit dem gleichen Pilz nur eine Phenolätherspaltung eintritt. 1-Äthyl-4-oxo-l,4,6,7,8,9-hexahydrobenzo[g]chinolin-3-carbonsäure (6) wird von Penicillium adametzi in 7- und 8-, von Streptomyces achromogenes in 7-(oder 8-) und 6- sowie von Spororrichum sulfurescens in 6-Stellung hydroxyliert. 5-Äthyl-8-oxo-2,3,5,8-tetrahydrofuro[2,3-g]-chinolin-7-carbonsäure (10) zeigt nur eine hydrolytische Spaltung des Dihydrofuranringes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060827
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  • 2
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlungen nichtsteroider Strukturen. IX Mikrobiologische Hydroxylierung von Δ8-Tetrahydrocannabinol (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3606-3614 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Transformations of Nonsteroidal Structures, IX Microbiological Hydroxylation of Δ8TetrahydrocannabinolΔ8Tetrahydrocannabinol (5) is hydroxylated at the ring system and the side chain by fermentations with Pellicularia flilamentosa or Streptomyces lavendulae. P. filamentosa yields the compounds 7β,3′- (1) und 7β,4′-dihydroxy-Δ8-tetrahydrocannabinol (3) as well as 8β,9α-dihydroxy-(2a) und 8β,9α,4′-trihydroxy-6a,10a-trans-hexahydrocannabinol (4a), whereas S. lavendulae leads to 7α-hydroxy- (6), 7α,2′- (7), 7α,3′- (8), 7α4′-Dihydroxy-Δ8-tetrahydrocannabinol (9) und 4′-hydroxy-7-oxo-Δ8-tetrahydrocannabinol (10).
    Notes: Δ8Tetrahydrocannabinol (5) wird durch Fermentationen mit Pellicularia filamentosa oder Streptomyces lavendulae gleichzeitig am Ringsystem und in der Seitenkette hydroxyliert. P. filamentosa ergibt die Produkte 7β,3′- (1) und 7β,4′-Dihydroxy-Δ8-tetrahydrocannabinol (3) sowie 8β,9α-Dihydroxy-(2a) und 8β,9α,4′-Trihydroxy-6A,10a-trans-hexahydrocannabinol (4a), während S. lavendulae zu 7α-Hydroxy-(6), 7α,2′- (7), 7α,3′- (8), 7α4′-Dihydroxy-Δ8-tetrahydrocannabinol (9) und 4′-Hydroxy-7-oxo-Δ8-tetrahydrocannabinol (10) führt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761091114
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  • 3
    Electronic Resource
    Electronic Resource
    1,2,3-Tricarbonylverbindungen, XII. Konstitutionsermittlung der Reaktionsprodukte von Ninhydrin mit 2-Aminophenol bzw. 2-Aminothiophenol (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 3954-3958 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,2,3-Tricarbonyl Compounds, XII. Elucidation of the Constitution of the Reaction Products of Ninhydrin with 2-Aminophenol and 2-AminothiophenolNinhydrin (1) reacts with 2-aminophenol (2) and 2-aminothiophenol (6) to give products the constitutions of which were elucidated by means of the 1H- and 13C NMR spectra to be 10a-hydroxy-indeno[2,1-b]benz[1,4]oxazine-11(10aH)-one (3) and 10a-hydroxy-indeno[2,1-b]benz-[1,4]thiazine-11(10aH)-one (7), respectively. Structures mentioned in the literature are on the one hand corrected and on the other hand doubtless established.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771101229
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  • 4
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlung von Steroiden, XV: Mikrobiologische Hydroxylierung von 3α-Acetoxy-5β-pregnan-20-carbonsäure und deren Methylester mit Calonectria decora und Syncephalastrum racemosum (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 2143-2151 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbial Transformations of Steroids, XV: Microbial Hydroxylation of 3α-Acetoxy-5β-pregnane-20-carboxylic Acid and of its Methyl Ester by Calonectria decora and Syncephalastrum racemosum3α-Acetoxy-5β-pregnane-20-carboxylic Acid (1) is hydroxylated by fermentation with Calonectria decora in 12β- (3), 7β,11β- (4), and 1β,12β-position (5) with hydrolysis of the 3-acetoxy group. The methyl ester 2 is attacked in 7α,12β- (6), 7β, 11α- (7), and 12β,15α-position (8), Syncephalastrum racemosum forms from 1 the hydroxy products in positions 11β (9), 12β (3), 7β,11β (4), and 11β,15β (10) as well as the further transformation products 3α-hydroxy- (13), 3α,11β-dihydroxy- (14), 3α,12β-dihydroxy-5β,20α-pregnane-20,18-carbolactone (11), and 11,18-epoxy-3α-hydroxy-5β,20α-pregnane-20,18-carbolactone (16), 1 is transformed by Mycobacterium smegmatis into methyl 3-oxo-pregnane- (18) and 3-oxo-1,4-pregnadiene-20-carboxylate (20).
    Notes: 3α-Acetoxy-5β-pregnan-20-carbonsäure (1) wird durch Fermentation mit Calonectria decora unter Verseifung der 3-Acetylgruppe in 12β- (3), 7β,11β- (4) und 1β,12β-Stellung (5) hydroxyliert. Der Methylester 2 wird analog in 7α,12β- (6), 7β,11α- (7) und 12β, 15α-Position (8) angegriffen. Syncephalastrum racemosum bildet aus 1 die Hydroxylierungsprodukte in den Positionen 11β (9), 12β (3), 7β,11β (4) und 11β,15β (10) sowie die weiteren Umwandlungsprodukte 3α-Hydroxy- (13), 3α,11β-Dihydroxy- (14), 3α,12β-Dihydroxy-5β,20α-pregnan-20,18-carbolacton (11) sowie 11,18-Expoxy-3α-hydroxy-5β,20α-pregnan-20,18-carbolacton (16). Durch Mycobacterium smegmatis wird 1 zu 3-Oxo-4-pregnen- (18) und 3-Oxo-1,4-pregnadien-20-carbonsäure-methylester (20) umgewandelt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110611
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  • 5
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlungen nichtsteroider Strukturen, III.I. und II. Mitteil.: H. Kosmol, K. Kieslich und H. Gihian, Liebigs Ann. Chem. 711, 38 bzw. 42 (1968). Hydroxylierung von 5-Alkyl-2-(benzolsulfonylamino)pyrimidinen und strukturverwandten Antidiabetika (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 1290-1302 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Transformations of Nonsteroidal Structures, III. Hydroxylation of 5-Alkyl-2-(benzenesulfonylamino)pyrimidines and Structurally Related Antidiabetics5-Alkyl-2-(arylsulfonylamino)pyrimidines (1-5 and 11-16) have been hydroxylated microbiologically Propyl, butyl, and isobutyl groups were hydroxylated at C-2, ethyl groups at C-1, isopropyl groups at C-1 and C-2, and neopentyl groups at C-3, respectively, by Streptomyces griseolus. The sulfonylurea part of the antidiabetics glibenclamid (25) and glisoxepid (29) was degradated to sulfonamide; in addition, hydroxyl groups were introduced into the 2- and 4-positions of the cyclohexane ring of 25.
    Notes: 5-Alkyl-2-(arylsulfonylamino)pyrimidine (1-5 und 11-16) wurden mikrobiologisch hydroxyliert. Mit Streptomyces griseolus wurden Propyl-, Butyl- und lsobutylgruppen an C-2, äthylgruppen an C-1, Isopropylgruppen an C-1 und C-2, sowie Neopentylgruppen an C-3 hydroxyliert. Die Antidiabetika Glibenclamid (25) und Glisoxepid (29) mit Sulfonylharnstoff-Struktur wurden zu Sulfonamiden abgebaut, ferner wurden in 2- und 4-Stellung des Cyclohexanrings von 25 Hydroxylgruppen eingeführt.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060426
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  • 6
    Electronic Resource
    Electronic Resource
    7-Aroyl-1H, 7H-s-triazolo[1,2-a]-s-triazol-1,3(2H)-dione, eine neue Klasse von Verbindungen aus 5-Phenyloxazolen und 4-Phenyl-4H-1,2,4-triazol-3,5-dion (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 641-648 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 7-Aroyl-1H,7H-s-triazolo (1,3(2H)-diones, a New Class of Compounds from 5-Phenyloxazoles and 4-Phenyl-4H-1,2,4-triazole-3,5-dioneThe 5-aryloxazoles 2a-e and their substituted derivatives 8a-c and 10 react with 4-phenyl-4H-1,2,4-triazole-3,5-dione (3) to give the new 7-aroyl-1H,7H-s-triazolo[1,2-a]- s-triazole-1,3(2H)-diones 5a-e, 9a-c, and 11. The structure is deduced from the 13C NMR spectroscopic data of 5b, 9a, and 11. The mechanism is shortly discussed.
    Notes: Durch Umsetzung der 5-Aryloxazole 2a-e sowie der substituierten Vertreter 8a-c und 10 mit 4-Phenyl-4H-1,2,4-triazol-3,5-dion (3) lassen sich die neuen 7-Aroyl-1H,7Hs-triazolo[1,2-a]-s- triazol-1,3(2H)-dione 5a-e, 9a-c und 11 herstellen. Die Struktur wird aus den 13C-NMR-spektroskopischen Daten von 5b, 9a und 11 abgeleitet. Der Mechanismus der Bildung wird kurz diskutiert.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840404
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  • 7
    Electronic Resource
    Electronic Resource
    Totalsynthese optisch aktiver Steroide, XX. Darstellung eines 7α-Methylöstratriens durch stereoselektive Methylierung von Östratrien-6-on (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 459-471 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Total Synthesis of Optically Active Steroids, XX1).  -  Synthesis of 7α-Methylestratriene by Stereoselective Methylation of Estratrien-6-one6-Cyanoestratriene 15 was oxidized by oxygen in a two-phase system to the 6-oxoestratriene 13. This is stereoselectively alkylated to the 7α-methylestratrienone 19a which is an intermediate for the synthesis of a highly potent estrogen.
    Notes: 6-Cyanöstratrien 15 wird durch Luftoxidation im Zweiphasensystem in das 6-Oxoöstratrien 13 übergeführt. Dieses wird stereoselektiv zum 7α-Methylöstratrienon 19a alkyliert, das ein Zwischenprodukt zur Synthese eines starken Östrogens darstellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820308
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  • 8
    Electronic Resource
    Electronic Resource
    Chemotherapeutische Nitroheterocyclen, XXVI. 5-Nitro-2-thiazolylpyrazole und 5-Nitro-2-thiazolylisoxazole aus 1,3-Dicarbonylverbindungen der Nitrothiazolreihe (1976)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1976 (1976), S. 13-21 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chemotherapeutic Nitroheterocycles, XXVI.  -  5-Nitro-2-thiazolylpyrazoles and 5-Nitro-2-thiazolylisoxazoles from 1,3-Dicarbonyl Compounds of the Nitrothiazole Series5-Nitrothiazole-2-carboxylic acid chloride (1) and copper salts of 1.3-dicarbonyl compounds 4 are used as starting materials for the synthesis of 1,3-dicarbonyl compounds 6 with a 5-nitro-2-thiazolyl moiety. Reaction of compounds 6 with substituted hydrazines or hydroxylamine affords the title compounds, some of which are mixtures of isomers.
    Notes: Aus dem 5-Nitrothiazol-2-carbonsäurechlorid (1) und Kupfersalzen von 1,3-Dicarbonylverbindungen 4 werden 1,3-Dicarbonylverbindungen 6 mit einem 5-Nitro-2-thiazolylrest hergestellt. Durch Umsetzung der Verbindungen 6 mit verschieden substituierten Hydrazinen oder Hydroxylamin werden die im Titel genannten Verbindungen synthetisiert, die zum Teil als Isomerengemisch vorliegen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197619760103
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