Die Spaltung von Phenoläthern mit Pyridinhydrochlorid

Prey, V.

doi:10.1002/cber.19410740715

Cited by 100 publications

(24 citation statements)

References 4 publications

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“…Melting points were taken on a Lindstroem apparatus and are uncorrected. 1 H and H-decoupled 13 spectra were recorded on a Bruker AC-200 spectrometer. IR and MS spectra were measured on a Perkin-Elmer 1600 FT-IR spectrometer and a Finnigan 4000 spectrometer.…”

Section: Methodsmentioning

confidence: 99%

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

et al. 1999

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During the last 10 years compounds have been discovered which can activate or block KATP channels. In particular, K channel activators (KCA) have been found to be smooth muscle relaxants with their main utility in hypertension and bronchodilation. In this paper we describe the synthesis of new KCA of the benzopyran type with a fixed 4-substituent and a systematic variation in the 6-position. The relaxant potency in rat aorta and trachea was used for biological characterization of the benzopyrans. In both biological test systems, they exhibit potency ranges of more than 3 log units. Structure-activity relationships are investigated by principal component analysis (PCA) and partial least-squares (PLS) analysis. Most striking outliers in an initial PLS analysis of the entire database were the unsubstituted 6-H compound 13 as well as 34 and 35. For the remaining set of 31 compounds, a 3-component PLS model explains the variance in biological activity to 81% in the aortic and to 82% in the tracheal test system. 6-Substituents influence affinity by a direct (presumably dipolar) interaction with the receptor site. According to the 2D-plot of the partial PLS weights, a strong electronegativity as well as high values for the integy moment and for the heat of formation in water dominate the first component; low values for substituent size (as defined by globularity or surface) are in addition favorable for high potency. High lipophilicity and low minimum energies of interaction dominate the second component. Chemical descriptors for the biological potency of the test set in rat aorta and rat trachea are very similar according to the almost identical projection of the Y-variables onto the X-component space.

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Section: Methodsmentioning

confidence: 99%

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

et al. 1999

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“…Heating in pyridine hydrochloride at 170" for several h (Exper. G) [9] yielded phenols 9b and 9d in good yield. On the other hand, 4-hydroxy-3-methoxymorphinans 6a-d were transformed by bromination, treatment with NaOH, and hydrogenation over PdjC to 4,5a -epoxymorphinans 10a-d (Exper.…”

Section: Hypothesismentioning

confidence: 95%

Design and Synthesis of Novel Opiate Antagonists with LH‐Stimulating Properties

Révész

Siegel

Buescher

et al. 1990

Helvetica Chimica Acta

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Opiate antagonists stimulate the release of LH and might, therefore, contribute to an innovative therapy for the treatment of numerous clinical syndromes characterized by hypofnnction of the HHG axis. The purpose of this work was to design and synthesize pure opiate antagonists useful for this therapy. Me, Et, Pr, and PhCH, groups were introduced at the crucial 14D-position of morphines and morphinans via a hetero-Diels-Alder key step starting from thebaine derivative 1 and tested for opiate antagonism and LH-stimulating activity. Me-, Et-, and Pr-substituted compounds 1la-C were stronger antagonists than naltrexone, whereas Pr and PhCH, substituents in l l c , l l d , 9d, 9d3, 9d4, and 9d5 led to orally active LH stimulators. Based on our finding that the y-antagonists 12 and lib5 showed no LH stimulation, we conclude that a Combination of both p -and x-antagonism is necessary for potent LH stimulation.Introduction. -Endogenous opiate peptides (EOP's) of the CNS participate in the regulation of the hypothalamo-hypophyseal-gonadal (HHG) axis. In rodents as well as in primates, the administration of opiate agonists leads to suppression of the secretion of luteinizing hormone (LH), while on the other hand, increased release of LH follows the application of opiate antagonists [ 11. Hypofunction of the HHG axis underlies numerous clinical syndromes such as the hypothalamic syndrome, idiopathic hypogonadotrophic hypogonadism, secondary hypothalamic hypogonadism, Kullmun's syndrome, delayed puberty, adolescent menstrual disorders, anorexia nervosa, and stress-related disorders. The presently available therapeutic approaches -human gonadotrophin, anti-estrogens, and pulsatile LHRH -all have inherent drawbacks and limitations associated with them. Opiate antagonists as LH secretion stimulators, therefore, represent a potential novel approach to their treatment.With the above background in mind, we have attempted to synthesize potent, longacting, and orally active opiate antagonists as LH-secretion stimulators. In the present article, we describe the design, synthesis, and LH-stimulating activities of a series of novel 14P-alkylated N-(cyclopropylmethy1)morphinans and -4,5a -epoxymorphinans.

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“…In der gleichen Weise wie bei X I X wurden 1,55 g (5,3 mMol) 2-[2'-Hydroxy-3'-chlor-5'-methylbenzyl]-3,5-dimethylhydrochinon (XVIII) und 1,52 g (8,8 mMol) 2-Chlor-4-methyl-6-hydroxymethylphenol in 10 ml Alkohol und insgesamt 3,5 ml konz. HCl kondensiert.…”

Section: 6-bis-[2'-hydro~y-3'-chl0r-5'-methylbenzyl]-35-dimethyl-hunclassified

Über die synthese und das redoxverhalten von molekulareinheitlichen hydrochinon‐phenol‐formaldehyd‐kondensaten. II

Manecke

Panoch

1966

Makromol. Chem.

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A T A T zum 60. Geburtstag gewidmet (Eingegangen am 8. M%rz 1965) ZUSAMMENFASSUNG:Mit dem Ziel, Modellsubstanzen fiir Redoxharze aus Hydrochinon, Phenol und Formaldehyd zu erhalten, wurden niedermolekulare, molekulareinheitliche Kondensate dieser Stoffe dargestellt. Das Redoxverhalten dieser Verbindungen mit bivalenten, tetravalenten oder hexavalenten Redoxsystemen wurde potentiometrisch untersucht. Versuche zur theoretischen Deutung der potentiometrischen Titrationskurven, insbesondere der hexavalenten Redoxsysteme, werden beschrieben. SUMMARY:With the aim to obtain model compounds for redox resins, composed of hydroquinone, phenol, and formaldehyde, low and uniform molecular weight condensates of this type were prepared. The redox characteristics of these divalent, tetravalent, and hexavalent compounds were investigated by potentiometric titration. An approach to interpret the titra-

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Die Spaltung von Phenoläthern mit Pyridinhydrochlorid

Cited by 100 publications

References 4 publications

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

6-Substituted Benzopyrans as Potassium Channel Activators: Synthesis, Vasodilator Properties, and Multivariate Analysis

Design and Synthesis of Novel Opiate Antagonists with LH‐Stimulating Properties

Über die synthese und das redoxverhalten von molekulareinheitlichen hydrochinon‐phenol‐formaldehyd‐kondensaten. II

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