Über Steroide. 45. Mitteilung. Darstellung homologer Bisdehydro‐doisynolsäuren. Über oestrogene Carbonsäuren V

Heer, J.; Miescher, K.

doi:10.1002/hlca.6602801212

Cited by 10 publications

(3 citation statements)

References 3 publications

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“…The C2 alkyl residues which are important for the activity of doisynolic acid [42], allenoic acid and the cyclohexene carboxylic acids, may also be considered as a part of substructure B. The highest activity among these molecules is associated with the isomers in which this alkyl residue has a cis relationship with the carboxylic acid function and its absolute stereochemistry corresponds to C 14a of d-E2 [39,41,43,44].…”

Section: B Substructural Binding Spec$icity Of E2 Des Doisynolic Amentioning

confidence: 99%

A possible basis for structure–function relationship of estrogens

Durani

Anand

1981

Int J of Quantum Chemistry

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It is well known that a wide variety of molecules compete for binding to the estrogen receptor and act as estrogens and/or antiestrogens. These molecules such as estradiol, diethylstilbestrol, doisynolic acid, the triarylethylenes, and cyclofenyl apparently share little resemblance which could account for their interaction with a common estrogen binding site. Knowledge of the receptor binding of triarylethylene and cyclofenyl prototypes, in particular, relative to that of the other estrogens is critical for understanding their structure-function relationship. We have carried out a study on the receptor binding specificity of triarylethylene and cyclofenyl prototypes. This study has revealed that these molecular types share considerable resemblance in their receptor binding specificity and differ from estradiol and other similar molecules in some important respects. However, comparison of their substructural binding specificities reveals the possibility that the triarylethylene and estradiol prototypes may interact with at least some common regions of the estrogen binding site. Based on this reasoning the comparative receptor binding of estrogens has been rationalized on the basis of a subsite hypothesis for the estrogen binding site. According to this hypothesis, the composite estrogen binding site is composed of essentially five subsites, and that the structurally different estrogenic prototypes can interact with different set of subsites, and thus differ in their binding orientation. The essential difference in the activity profile of estradiol prototypes and the triarylethylene antiestrogens reveals the possibility of a causal relationship between the binding orientation of a ligand and its activity profile. This model for receptor site can thus serve as a working hypothesis to rationalize the structure-function relationship of estrogens.

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Section: B Substructural Binding Spec$icity Of E2 Des Doisynolic Amentioning

confidence: 99%

A possible basis for structure–function relationship of estrogens

Durani

Anand

1981

Int J of Quantum Chemistry

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“…The Ciba group was able to isolate three of the four theoretically possible racemates from the keto ester 90. The major product was found to possess the "natural" configuration and was designated ketone A (91). Another isomer, ketone C (92), could be tranformed to ketone A (91) by treatment with alcoholic alkali.…”

Section: Synthesis According To Anner and Mieschermentioning

confidence: 99%

“…In a brilliant series of papers [86][87][88][89][90][91][92][93][94] they also described the total synthesis of this compound (Scheme 3-11). The keto ester 15, an intermediate in Bachmann's synthesis of equilenin (Scheme 3-2), was treated with ethylmagnesium bromide to form the hydroxy ester 117.…”

Section: Bisdehydrodoisynolic Acidmentioning

confidence: 99%

Ab → Abc → Abcd

1974

Organic Chemistry: A Series of Monographs

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Über Steroide. 46. Mitteilung. Ein einfacher Abbau der Gallensäuren‐Seitenkette zur Methylketonstufe IV. Der Abbau der 3β‐Oxy‐allo‐cholansäure und der 3α‐Oxy‐cholansäure (Lithocholsäure)

Meystre

Miescher

1946

Helvetica Chimica Acta

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Volumen XXIX, Pasciculus I (1946). 33T e x t z u d e n F i g u r e n . Fur die Figuren 1-4 sind der Reihe nach fur n3 (Zahl der Trennstufen ma1 Trennfaktor der nicht vervollkommneten Einzeldestillation) die Werte 0,3; 1 ; 5 und 10 zugrunde gelegt. Als Abszisse ist ~ aufgetragen (Menge der bis zum betreffenden Punkte als Destillat entnommenen Hubstanz, geteilt durch die ursprunglich eingesetzte Substanzmenge). Als Ordinaten sind die Konzentrationen des leicht fluchtigen Bestandteils in der Blase ( y B ; punktierte Kurven) und im ubergehenden DestiUat ( y D ; ausgezogene Kurven) aufgetragen. Dabei sind in jeder Figur 3 verschiedene Ausgangskonzentrationen zugrunde gelegt, namlich yn, = 0,1 (schwache Kurven) y B , = 0,5 (starke Kurven) und y B , = 0,9 (mittelstarke Kurven).Mit nB = 10 konnen beide Komponenten in praktisch 100-proz. Ausbeute vollstandig voneinander getrennt werden (Fig. 4). I n einer nachfolgenden Arbeit sollen die entsprechenden Uberlegungen und Ergebnisse fur Gemische, welche aus beliebig vielen K o m p o n e n t e n bestehen, mitgeteilt werden. mD n, Physikalisch-Chemisches Institut der Universitat Basel. 7. Uber Steroide. Ein einfaeher Abbau der Gallensauren-Seitenkette zur Methylketonstufe IV. Der Abbau der 3~-Oxy-allo-eholansaure und der 3 a-Oxy-eholansaure (Lithoeholsaure) von Ch. Meystre und K. Miescher. (29. XI. 45.) 46. Mitteilungl).

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Über Steroide. 45. Mitteilung. Darstellung homologer Bisdehydro‐doisynolsäuren. Über oestrogene Carbonsäuren V

Cited by 10 publications

References 3 publications

A possible basis for structure–function relationship of estrogens

A possible basis for structure–function relationship of estrogens

Ab → Abc → Abcd

Über Steroide. 46. Mitteilung. Ein einfacher Abbau der Gallensäuren‐Seitenkette zur Methylketonstufe IV. Der Abbau der 3β‐Oxy‐allo‐cholansäure und der 3α‐Oxy‐cholansäure (Lithocholsäure)

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