Synthesis and stereochemistry of prostacyclin and synthesis of 6-ketoprostaglandin F1.alpha.

Ra, Johnson; Fh, Lincoln; Jl, Thompson; Eg, Nidy; Sa, Mizak; Axen, Udo

doi:10.1021/ja00454a060

Cited by 133 publications

(35 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This confirms that H-5 is cis to C-7 and not trans. This configuration of H-5 was previously shown on the basis of chemical shift additivities (12), an empirical approach, whereas the nOe is quantitative in determining points of configuration. Finally, saturation of H-11 proves that H-12 is a to the ring, as expected, since an nOe is not observed for H-12 (Fig.…”

Section: Discussionmentioning

confidence: 55%

See 1 more Smart Citation

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

Kotovych¹,

Aarts²,

Nakashima³

et al. 1980

Can. J. Chem.

View full text Add to dashboard Cite

The proton magnetic resonance (1H nmr) spectrum at 400 MHz of prostacyclin at pH 10.4 in glycine buffer has been completely analyzed utilizing homonuclear double resonance, inversion recovery, and difference nOe experiments. The spectral analysis shows that the two protons at C-4 are non-equivalent even though they are removed from the asymmetric centres at C-8 and C-9 by five bonds. The difference nOe measurements verify the configuration at C-5.Proton longitudinal relaxation times (T1) were measured at 400 and 200 MHz. From the T1 frequency dependence, effective rotational correlation times ranging from 2.3 × 10−10 to 3.0 × 10−10 s were calculated for H-5, H-9, H-11, and H-15. This indicates that the portion of the molecule encompassed by these protons has a longer correlation time than is observed for the C-2 and the C-17 to C-19 protons, for which the average correlation time is 1.2 × 10−10 s. Hence the aliphatic side chains have more segmental motion.

show abstract

Section: Discussionmentioning

confidence: 55%

“…The chemical shifts of H-9, H-5, H-15, and H-1 1 are in the same order as those observed for the PGI, methyl ester in CDCl, (12). In fact, the presence of the H-9 multiplet in the range of 4.45-4.55 ppm has been used (13) to assign compounds stereochemically related to (6s)-5,6-dihydroprostacyclin.…”

Section: Discussionmentioning

confidence: 70%

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

Kotovych¹,

Aarts²,

Nakashima³

et al. 1980

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…The true potency of PGI2 is difficult to assess because of the very rapid breakdown to the far less active product 6-oxo-PGF1, (25). Thus estimates of potency in a given system depend upon the mode of administration and the propensity for decomposition.…”

Section: Ap Accumulationmentioning

confidence: 99%

Specific inhibition by prostaglandins E2 and I2 of histamine-stimulated [14C]aminopyrine accumulation and cyclic adenosine monophosphate generation by isolated canine parietal cells.

Soll¹

1980

J. Clin. Invest.

143

View full text Add to dashboard Cite

“…The sodium salt of prostacyclin (Johnson, Lincoln, Thompson, Nidy, Mizsak & Axen, 1977;Whittaker, 1977) In four experiments, hamsters were given aspirin orally (500 mg/kg) 1-2 h before the aortae were removed.…”

Section: Assay Of Prostacyclin Activitymentioning

confidence: 99%

PROSTACYCLIN (PGI₂) INHIBITS THE FORMATION OF PLATELET THROMBI IN ARTERIOLES AND VENULES OF THE HAMSTER CHEEK POUCH

Higgs

Moncada

et al. 1978

British J Pharmacology

View full text Add to dashboard Cite

1 Isolated rings of hamster aorta produced an unstable substance which inhibited platelet aggregation in vitro and had the same characteristics as prostacyclin. 2 Prostacyclin inhibited adenosine diphosphate (ADP)-induced aggregation of hamster platelets in vitro.3 The effects of prostacyclin on ADP-induced platelet thrombi in the microcirculation of the hamster cheek pouch were studied with a television microscope. 4 Prostacyclin caused a dose-dependent increase in the time of iontophoretic application of ADP which was required to induce platelet thrombi formation and embolization in venules (30 to 40 gm diameter).5 Prostacyclin caused a dose-dependent reduction in the total time during which ADP-induced thrombi were observed following local electrical damage to arterioles (40 to 80 gm diameter). 6 Thrombus formation in venules and arterioles was abolished by 500 ng/ml prostacyclin in the Krebs solution superfusing the hamster cheek pouch. 7 Prostacyclin was approximately twenty times more potent than prostaglandin E1 in preventing thrombus formation in the microcirculation.

show abstract

Synthesis and stereochemistry of prostacyclin and synthesis of 6-ketoprostaglandin F1.alpha.

Cited by 133 publications

References 6 publications

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

Specific inhibition by prostaglandins E2 and I2 of histamine-stimulated [14C]aminopyrine accumulation and cyclic adenosine monophosphate generation by isolated canine parietal cells.

PROSTACYCLIN (PGI₂) INHIBITS THE FORMATION OF PLATELET THROMBI IN ARTERIOLES AND VENULES OF THE HAMSTER CHEEK POUCH

Contact Info

Product

Resources

About

Synthesis and stereochemistry of prostacyclin and synthesis of 6-ketoprostaglandin F1.alpha.

Cited by 133 publications

References 6 publications

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

Specific inhibition by prostaglandins E2 and I2 of histamine-stimulated [14C]aminopyrine accumulation and cyclic adenosine monophosphate generation by isolated canine parietal cells.

PROSTACYCLIN (PGI2) INHIBITS THE FORMATION OF PLATELET THROMBI IN ARTERIOLES AND VENULES OF THE HAMSTER CHEEK POUCH

Contact Info

Product

Resources

About

PROSTACYCLIN (PGI₂) INHIBITS THE FORMATION OF PLATELET THROMBI IN ARTERIOLES AND VENULES OF THE HAMSTER CHEEK POUCH