The Chemistry and the Physiological Action of Khellin and Related Products.

Huttrer, Charles P.; Dale, Estaleta.

doi:10.1021/cr60151a003

Cited by 50 publications

(10 citation statements)

References 27 publications

(49 reference statements)

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“…Siegfried Goldmann was born in Molln in 1947. He studied chemistry at Marburg and was awarded a doctorate with distinction in 1979 for his work on ,,The stereochemistry of the (2,3]…”

Section: Synthesis Of Enantiomerically Pure 1 Cdihydropyridinesmentioning

confidence: 99%

1,4‐Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities

Goldmann

Stoltefuß

1991

Angew. Chem. Int. Ed. Engl.

453

224

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Dedicated to Professor Karl Heinz Biichel on the occasion of his 60th birthday4-Aryl-I ,4-dihydropyridine-3,5-dicarboxylic diesters of the nifedipine type have become almost indispensable for the treatment of cardiovascular diseases since they first appeared on the market in 1975. There are some twenty derivatives currently under clinical development worldwide and work in this area is continuing undiminished. The 1,4-dihydropyridines are the most effective of the calcium antagonists or calcium channel blockers. They are valued not only for their pharmacological effect, but also as a tool for the investigation of the calcium channel, particularly since the discovery that this class also includes compounds that have exactly the opposite action profile and are known as calcium agonists. There are even instances in which this reversal of activity is found between enantiomers. In view of the importance of chirality to pharmacological activity, the present article will describe methods for the separation of enantiomers, point out the structural differences between calcium antagonists and calcium agonists, and attempt to explain the difference in their behavior.

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“…Siegfried Goldmann was born in Molln in 1947. He studied chemistry at Marburg and was awarded a doctorate with distinction in 1979 for his work on ,,The stereochemistry of the (2,3]…”

Section: Synthesis Of Enantiomerically Pure 1 Cdihydropyridinesmentioning

confidence: 99%

1,4‐Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities

Goldmann

Stoltefuß

1991

Angew. Chem. Int. Ed. Engl.

453

224

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“…Khellin and related furochromones have long been used as antispasmedics, as vasodilators, and for a variety of other medicinal purposes (Huttrer and Dale, 1951). Imperatorin, like the bergapten of celery, has been shown to be an extremely potent fish poison.…”

Section: Piimentioning

confidence: 99%

The Organic Constituents of Food. II. Celery^a

Crosby

Anderson

1963

Journal of Food Science

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“…The main constituents of the umbelliferous plant Ammi visnaga Lam., khellin, visnagin, and chellol-glucoside, have been thoroughly investigated chemically as well as pharmacologically (3,4,5,6) but ollly a few investigations of minor constituents have been published (3).…”

mentioning

confidence: 99%

On Khellactone

Späth¹,

Gruber²,

Matzke³

1953

Can. J. Chem.

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A hitherto unknown minor constituent of the seeds of Ammivisnaga Lam is converted under the influence of 5% alcoholic potassium hydroxide into a compound which seems to be a coumarin. Treatment with methyl-alcoholic alkali yields a substance C15H16O5, whereas treatment with ethyl-alcoholic alkali gives a substance C16H18O5. Dehydrating agents convert both optically active compounds into the same optically inactive dehydration product C14Hl2O4 (Substance A). The further investigations carried out with Substance A were: oxidation, after methylation, which yielded α-hydroxyisobutyric acid; fusion with potassium hydroxide, which gave phloroglucinol. On treatment with diluted caustic alkalies two definite products, C10H6O5, probably an acid, and C11H8O4, a ketone, were obtained.

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The Chemistry and the Physiological Action of Khellin and Related Products.

Cited by 50 publications

References 27 publications

1,4‐Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities

1,4‐Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities

The Organic Constituents of Food. II. Celery^a

On Khellactone

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The Chemistry and the Physiological Action of Khellin and Related Products.

Cited by 50 publications

References 27 publications

1,4‐Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities

1,4‐Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities

The Organic Constituents of Food. II. Celerya

On Khellactone

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Product

Resources

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The Organic Constituents of Food. II. Celery^a