Tr�nenreizstoffe als Akzeptoren f�r Dihydropyridinwasserstoff

Wallenfels, Kurt; Ertel, W.; Höckendorf, A.; Rieser, J.; Überschär, K. H.

doi:10.1007/bf00600500

Cited by 13 publications

(5 citation statements)

References 25 publications

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“…In this respect, we report here the results of an asymmetric reduction with new types of the chiral Hantzsch ester prepared in the present study, and a remarkable improvement in the reduction conditions and chemical yields for the asymmetric reduction of non-activated carbonyl compounds by using the N-anionized form of the chiral Hantzsch ester (1). potassium alkoxide.…”

Section: -Smentioning

confidence: 73%

“…The results were compared with th'ose by using sodium or Preparation of chital 1,4-dihydropyridines. According to the standard condensation reaction 12 ) as applied for the preparation of 1,8) novel chiral 1,4-dihydropyridines (4, 6, and 9) were prepared as follows (Scheme 1).…”

Section: -Smentioning

confidence: 99%

“…However, although the dihydropyridines showed a single spot on TLC, it was difficult to isolate them completely from the residual solvent of the column chromatography in a solvent-free pure form, which might be feasible for combustion analysis, since they were noncrystalline solid or syrupy substances after RESULTS AND DISCUSSION (1) asymmetric reductions of methyl benzoylformate,9) iminium salts,10) and It,lt,lt-trifluoroacetophenone 11 ) have been conducted. The observed enantiomeric excess was lOr-..; 78 %, including double asymmetric induction.…”

Section: -Smentioning

confidence: 99%

“…Rf=0. 9 (benzene (5): methanol (1) (10). The reduced form 9 (20 mg, 0.032 mmol) was thoroughly mixed with sulfur (20 mg, 0.62 mmol) and the mixture was heated to 150°C in an oil bath for about 90 min.…”

Section: ( -)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl Acetoacetmentioning

confidence: 99%

“…1 ) In addition to this, simulation of enzyme stereoselectivity by using synthetic chiral NADH model compounds has been an alluring topic in recent years.…”

mentioning

confidence: 99%

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NADH Model Reaction: Asymmetric Reduction of Non-activated Carbonyl Compounds with N-Anionized Hantzsch Ester

Watanabe

Fushimi

Baba

et al. 1985

Agricultural and Biological Chemistry

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Section: -Smentioning

confidence: 73%

Section: -Smentioning

confidence: 99%

Section: -Smentioning

confidence: 99%

Section: ( -)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl Acetoacetmentioning

confidence: 99%

“…1 ) In addition to this, simulation of enzyme stereoselectivity by using synthetic chiral NADH model compounds has been an alluring topic in recent years.…”

mentioning

confidence: 99%

See 3 more Smart Citations

NADH Model Reaction: Asymmetric Reduction of Non-activated Carbonyl Compounds with N-Anionized Hantzsch Ester

Watanabe

Fushimi

Baba

et al. 1985

Agricultural and Biological Chemistry

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Die Organoschwefelchemie der Gattung Allium und ihre Bedeutung für die organische Chemie des Schwefels

Block

1992

Angewandte Chemie

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Dieser Aufsatz ist ein Streifzug durch die Organoschwefelchemie der Gattung Allium, zu der unter anderem Knoblauch und Zwiebel gehören. Wir berichten über die Biosynthese der S‐Alk(en)yl‐L‐cystein‐S‐oxide (Aroma‐ und Geruchsvorstufen) in den intakten Pflanzen und darüber, wie diese Vorstufen beim Zerschneiden oder Zerdrücken der Pflanzen durch Allinase‐Enzyme zu Sulfensäuren — hochreaktiven Organoschwefel‐Zwischenprodukten — gespalten werden. Während im Knoblauch aus 2‐Propensulfensäure Allicin, ein Thiosulfinat mit antibiotischen Eigenschaften, entsteht, wird in Zwiebelgewächsen 1‐Propensulfensäure zum Sulfin (Z)‐Propanthial‐S‐oxid, dem tränenreizenden Faktor (LF), umgelagert. Zu den Highlights aus der Chemie der Zwiebel zählen die Zuordnung der Stereochemie des tränenreizenden Faktors und der Mechanismus seiner Dimerisierung; die Isolierung, Charakterisierung und Synthese von Thiosulfinaten, die möglichst genau Geschmack und Aroma einer gerade zerschnittenen Zwiebel nachahmen, sowie von anderen ungewöhnlichen Verbindungen wie den Zwiebelanen (Dithiabicyclo[2.1.1]hexanen), einem Bissulfin (Butandithial‐S,S′‐dioxid), anti‐thrombotischen und antiasthmatischen Cepaenen (α‐Sulfinyldisulfiden) und vic‐Disulfoxiden. Besonders bemerkenswert in der Chemie des Knoblauchs sind die Entdeckung des Ajoens, eines wirksamen Antithrombosemittels aus Knoblauch, und die Aufklärung der ungewöhnlichen Reaktionssequenz, die beim Erhitzen von Diallyldisulfid abläuft, das in Wasserdampf‐destilliertem Knoblauchöl vorkommt. Diskutiert werden [3,3]‐ und [2,3]‐sigmatrope Umlagerungen unter Beteiligung von Schwefel (z.B. Sulfoxid‐beschleunigte Thio‐ und Dithio‐Claisen‐Umlagerungen) und Cycloadditionen mit Thiocarbonylsystemen. Angesichts der kulinarischen Bedeutung der Allium‐Gewächse sowie deren Anwendung in der Volksmedizin wird schließlich noch die physiologische Wirksamkeit der Inhaltsstoffe dieser Pflanzen erörtert: Krebsvorbeugung, antimikrobielle Aktivität, Wirksamkeit als Lock‐ oder Abwehrstoffe bei Tieren oder Insekten, Geruchs‐, Geschmacks‐ und tränenreizende Eigenschaften, Wirkung auf den Fett‐Metabolismus, Hemmung der Plättchenaggregation im Fall von Ajoen. Anmerkungen über Mundgeruch und Sodbrennen durch Zwiebeln oder Knoblauch dürfen natürlich nicht fehlen.

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The Organosulfur Chemistry of the Genus Allium – Implications for the Organic Chemistry of Sulfur

Block

1992

Angew. Chem. Int. Ed. Engl.

982

701

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A Cook's tour is presented of the organosulfur chemistry of the genus Allium, as represented, inter alia, by garlic (Allium sativum L.) and onion (Allium cepa L.). We report on the biosynthesis of the S-alk(en)yl-L-cysteine S-oxides (aroma and flavor precursors) in intact plants and on how upon cutting or crushing the plants these precursors are cleaved by allinase enzymes, giving sulfenic acids-highly reactive organosulfur intermediates. In garlic, 2-propenesulfenic acid gives allicin, a thiosulfinate with antibiotic properties, while in onion I-propenesulfenic acid rearranges to the sulfine (2)-propanethial S-oxide, the lachrymatory factor (LF) of onion. Highlights of onion chemistry include the assignment of stereochemistry to the LF and determination of the mechanism of its dimerization; the isolation, characterization, and synthesis of thiosulfinates which most closely duplicate the taste and aroma of the freshly cut bulb, and additional unusual compounds such as zwiebelanes (dithiabicyclo(2.1. llhexanes), a bissulfine (a 1,4-butanedithial S,Y-dioxide), antithrombotic and antiasthmatic cepaenes (asulfinyl disulfides), and vic-disulfoxides. Especially noteworthy in the chemistry of garlic are the discovery of ajoene, a potent antithrombotic agent from garlic, and the elucidation of the unique sequence of reactions that occur when diallyl disulfide, which is present in steam-distilled garlic oil, is heated. Reaction mechanisms under discussion include [3,3]-and [2,3]-sigmatropic rearrangements involving sulfur (e.g. sulfoxide-accelerated thio-and dithio-Claisen rearrangements) and cycloadditions involving thiocarbonyl systems. In view of the culinary importance of alliaceous plants as well as the unique history of their use in folk medicine, this survey concludes with a discussion of the physiological activity of the components of these plants: cancer prevention, antimicrobial activity, insect and animal attractive/repulsive activity, olfactory-gustatory-lachrymatory properties, effect on lipid metabolism, platelet aggregation inhibitory activity and properties associated with ajoene. And naturally, comments about onion and garlic induced bad breath and heartburn may not be overlooked.

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Tr�nenreizstoffe als Akzeptoren f�r Dihydropyridinwasserstoff

Cited by 13 publications

References 25 publications

NADH Model Reaction: Asymmetric Reduction of Non-activated Carbonyl Compounds with N-Anionized Hantzsch Ester

NADH Model Reaction: Asymmetric Reduction of Non-activated Carbonyl Compounds with N-Anionized Hantzsch Ester

Die Organoschwefelchemie der Gattung Allium und ihre Bedeutung für die organische Chemie des Schwefels

The Organosulfur Chemistry of the Genus Allium – Implications for the Organic Chemistry of Sulfur

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