Kohlenhydrate, XIX. Mitteil.: Synthetische Derivate der Fructo‐furanose

Brigl, Percy; Schinle, Richard

doi:10.1002/cber.19340670511

Cited by 6 publications

(4 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Using nitrile group as a dipolarophile the sugar substituted nitrile (4) readily participated in a [2+3] cycloaddition reaction with arylsulfonyl azide as 1,3-dipole, yielding five membered heterocyclic tetrazole systems. The IR absorption bands were utilized to characterize specific structure for compounds (16)(17)(18). The disappearance of the bands at 2200 cm -1 and 2137 cm 1 attributed to nitrile group and azide group stretching frequency is good evidence for the success of this reaction.…”

Section: Resultsmentioning

confidence: 99%

“…aurous. Compounds (11,12,18, and 21) were nearly as active as the antibiotics against the Gram negative E. Coli with (21) being the most active. Moreover compounds (11, 12, 15, and 21) show similar activity against the yeast (Candidas) as two antibiotics taken as standard for comparision.…”

Section: Biological Screening: Antimicrobial Activity Testsmentioning

confidence: 98%

“…Moreover compounds (11, 12, 15, and 21) show similar activity against the yeast (Candidas) as two antibiotics taken as standard for comparision. Compounds (12,15,16,18, and 21) were more active than Ampicilline and Gentamycine against the pathogenic fungi Spergillus flavus, while compounds (11, 15, and 21) were more active against pencillum spp than the two antibiotics.…”

Section: Biological Screening: Antimicrobial Activity Testsmentioning

confidence: 98%

“…The activities were determined in vitro using disc diffusion method against staphaureus, Eschericha coli and three pathogenic strains of yeast (Candida) and fungus (Aspergillus flaveus and pencillium spp.) Three types of new sugar-based monocyclic triazole, triazoline and tetrazole derivatives of D-fructose have been synthesized and According to reported method [18] when compound (1) was treated with 45% HBr solution in glacial acetic acid it gave 1,3,4,6tetra-O-benzoyl--D-fructofuranosyl bromide (2). Treatment of the benzoylated bromide with sodium azide afforded sugar azide (3).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of New Carbohydrate Derivatives Via 1,3-Dipolarcycloaddition Reaction

Sharba¹,

Al-Fattahi²,

Askar³

2011

JNUS

View full text Add to dashboard Cite

This work describes the synthesis of a new fructofuranosyl derivatives comprising 1,2,3triazole, 1,2,3-triazoline or tetrazole rings via 1,3-dipolar cycloaddition reaction. To obtain these derivatives, 1,3,4,6-tetra-O-benzoyl--D-fructofuranose (1) with free hydroxyl group at position-2 was prepared as the starting material. Reaction of compound (1) with 45% HBr solution in glacial acetic acid gave compound (2). The bromide (2) was then made to react with some nucleophiles (NaN 3 and KCN) to give 1,3,4,6-tetra-O-benzoyl--D-fructofuranosyl azide (3) and 1,3,4,6-tetra-O-benzoyl--D-fructofuranosyl cyanide (4). Treatment of compound (3) with cinnamic acid, cinnamaldehyde, acrylic acid, acrylonitrile, acrylamide and maleic anhydride, gave the triazoline derivatives (5-10). Cycloaddition reaction was also carried out with propargyl chloride, propargyl alcohol and 1-hexyn-3-ol using (ph 3 P) 3 CuI as a catalyst to give the triazole derivatives (12-14). Reaction of the cyanosugar (4) with arylsulfonyl azides gave the tetrazole derivatives (16-18). Antibacterial and antifungal activities of some novel synthesized compounds were studied and compared with that of two well known antibiotics (Ampicillin and Gentamycin).

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Biological Screening: Antimicrobial Activity Testsmentioning

confidence: 98%

Section: Biological Screening: Antimicrobial Activity Testsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of New Carbohydrate Derivatives Via 1,3-Dipolarcycloaddition Reaction

Sharba¹,

Al-Fattahi²,

Askar³

2011

JNUS

View full text Add to dashboard Cite

show abstract

Kohlenhydrate, XX. Mitteil.: Neue Synthesen der Gentiobiose und der 1‐(β‐Glucosido)‐fructose

Brigl

Widmaier

1936

Ber. dtsch. Chem. Ges. A/B

View full text Add to dashboard Cite

In friiheren Arbeiten von Brigl und Mitarbeitern sind zwei Benzal-Derivate beschrieben, die nur eine freie Hydroxylgruppe enthalten und deswegen ZW Disaccharid-Synthese geeignet erscheinen. Es sind dies die 3.5-Benzal-manoaceton-glucose von Brigl und Griiner') und die Dibenzalfructose von Brigl und Schinles). Benzal-Derivate krystdlisieren meist gut und haben den weiteren Vorteil, d& der Aldehyd nicht nur mit Siiuren, sondern auch durch katalytisch erregten Wasserstoff entfernbar ist').Vor der Verwendung dieser Substamen zu Synthesen mul3te &re Konstitution, vor allem also die Lage der freien Hydroxylgruppe ganz einwandfrei festliegen. Bei der Benzal-monoaceton-glucose bestand nur insofern eine Unsicherheit, als hier 2 Substamen mit gleichem Schmelzpunkt und gleicher Drehung in der Literatur beschrieben sind, fiir die aber verschiedene Xonstitution in Anspruch genommen wird. 1) XIX. Mitteil.: Brigl u. Schinle, B. 67, 754 [1934].

show abstract

Synthese anomerer Sialinsäure‐methylketoside

1966

View full text Add to dashboard Cite

Über die Acetochlor‐Verbindung des Lactaminsäure‐methylesters wurde nach Koenigs‐Knorr ein Methylketosid‐methylester von [α] D20: −6° erhalten, der von Neuraminidase quantitativ gespalten wird. Der aus Lactaminsäure mit H⊕ und Methanol dargestellte anomere Methylketosid‐methylester von [α]D20: −46° wird von dem Enzym nicht angegriffen. Bei den durch Verseifung der CO2CH3‐Gruppen erhaltenen anomeren Methoxycarbonsäuren besteht derselbe Unterschied.

show abstract

Kohlenhydrate, XIX. Mitteil.: Synthetische Derivate der Fructo‐furanose

Cited by 6 publications

References 11 publications

Synthesis of New Carbohydrate Derivatives Via 1,3-Dipolarcycloaddition Reaction

Synthesis of New Carbohydrate Derivatives Via 1,3-Dipolarcycloaddition Reaction

Kohlenhydrate, XX. Mitteil.: Neue Synthesen der Gentiobiose und der 1‐(β‐Glucosido)‐fructose

Synthese anomerer Sialinsäure‐methylketoside

Contact Info

Product

Resources

About