Structure cristalline et moléculaire de l'oestradiol hemihydraté

Busetta, B.; Hospital, M.

doi:10.1107/s0567740872002754

Cited by 62 publications

(21 citation statements)

References 4 publications

(4 reference statements)

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“…The structure of 5 shows that the steroid's skeletal arrangement is not noticeably different from that of 17 β ‐estradiol 18. Structural analysis confirmed the position of the ruthenocenyl group at 17 α .…”

Section: Resultsmentioning

confidence: 84%

Novel Estradiol Derivatives Labeled with Ru, W, and Co Complexes. Influence on Hormone-Receptor Affinity of Several Organometallic Groups at the 17 Position

et al. 2002

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„Seifenblasen“: Protonen werden an einer weichen Grenzfläche zwischen Wasser und 1,2‐Dichlorethan (DCE) unter Wasserstoffentwicklung durch [(C5Me5)2Fe] reduziert. Dabei folgt auf einen durch [(C5Me5)2Fe] unterstützten Protonentransfer durch die Grenzfläche die Reduktion der Protonen in DCE. Die Grenzfläche dient vorrangig als Protonenpumpe, mit deren Hilfe bei der Wasserstoffentwicklung direkt auf die wässrigen Protonen zugegriffen werden kann.

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Section: Resultsmentioning

confidence: 84%

Novel Estradiol Derivatives Labeled with Ru, W, and Co Complexes. Influence on Hormone-Receptor Affinity of Several Organometallic Groups at the 17 Position

et al. 2002

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“…208 (5) 6860 (4) 9189 (3) 3.5 C (2) 28 (5) 6391 (4) 8131 (3) 3.7 C (3) 1678 (5) 6537 (4) 7594 (3) 3.5 C (4) 3433 (5) 7117 (4) 8163 (3) 3.3 C (5) 3662 (4) 7575 (4) 9216 (3) 3.1 C (6) 5656 (5) 8117 (5) 9762 (3) 4.2 C (7) 5764 (5) 8964 (5) 10806 (3) 3.9 C (8) 4071 (4) 8131 (4) 11489 (3) 3.0 C (9) 2171 (4) 8091 ( • ~,~ (Norton, Kartha & Lu, 1964;Busetta & Hospital, 1972;Busetta, Courseille, Geoffre & Hospital, 1972;Duax, 1972), 4FE2 has an extended structure. Bond lengths and most bond angles do not deviate significantly among the estratriene analogs.…”

Section: Discussionmentioning

confidence: 99%

Structure of 4-fluoro-1,3,5(10)-estratriene-3,17β-diol–hemimethanol

Go¹,

Kartha²,

Neeman³

1982

Acta Crystallogr Sect B

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Abstract. ClsH23FO2.½CH3OH, triclinic, P1, a = 7.367 (1), b= 9.363 (6), c = 12.531 (1) A,, a= 89.31 (3), /? = 93.38 (1), y = 109.62 (3) ° , V = 812.8/k 3, Z = 2. The structure was solved by direct methods and refined by block-diagonal least squares to an R factor of 6.2% for 3043 observed reflections. The general features of the steroid are similar to those of other estratriene analogs. Molecules in the crystal are linked together in a head-to-tail fashion between the O at C(3) and at C (17), and sideways between the hydroxyls of the solvent and the steroid.Introduction. Tumor inhibitory effects on estrogen administration have been observed in breast and prostatic cancers and attempts have been made to obtain modified steroidal estrogens that will be useful in cancer chemotherapy. In this connection it is seen that in contrast to the biologically inactive bromo analog, 4-fluoroestratrienediol (4FE2) is a very highly active estrogen. The present crystallographic study of the structure and conformation of 4FE2 was undertaken to establish the stereochemical reason, if any, for the striking difference in biological activity of the two analogs.A crystal of about 1.3 × 0.8 × 0.3 mm crystallized from benzene was used to collect the diffraction data. The crystals are triclinic with space group P I. Lattice parameters were refined by a least-squares fit to a set of 24 measured reflections in a 0 range 10-34 ° (Cu Ka). Three-dimensional data were collected on an Enraf-Nonius CAD-4 automated diffractometer using Ni-filtered Cu Kct radiation by o.~--20 scans within the Cu sphere of 20 to 150 °. The measured intensities were converted to structure amplitudes in the usual manner, and corrected for Lorentz, polarization, and absorption effects. There were 3436 unique reflections measured, of which 3043 had intensities greater than 2o(1) and were used in the determination and refinement of the structure.

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“…la and b), Keasling and Schueler (9) proposed that the structural requirements for estrogenicity were a specific distance (14.5 A) between two hydroxyl groups separated by a flat hydrophobic region. Subsequent X-ray crystallographic studies have revealed that the distances between the terminal oxygen groups in estradiol (10) and diethylstilbestrol (11) are 10.9 and 12.1 A (Fig. 2a and b), respectively, and that the molecules (particularly DES) are not as flat as their conventional chemical drawings might suggest.…”

Section: Estradiol and Diethylstilbestrolmentioning

confidence: 99%

Molecular conformation, receptor binding, and hormone action of natural and synthetic estrogens and antiestrogens.

Duax¹,

Griffin²,

Weeks³

et al. 1985

Environ Health Perspect

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The X-ray crystallographic structural determinations of synthetic estrogens and antiestrogens provide reliable information on the global minimum energy conformation of these molecules or a local minimum energy conformation that is within 1 or 2 kcal/mole of the global minimum. In favorable cases, state-ofthe-art molecular mechanics calculations provide quantitative agreement with X-ray results and information on the relative energy ofother local minimum energy conformations not observed crystallographically.Because the conformation of diethylstilbestrol (DES) observed in solvated crystals has an overall conformation and dipole moment more similar to estradiol it is the form more likely to bind to the receptor and produce hormone activity. Either phenol ring of DES can successfully mimic the estradiol A-ring in binding to the receptor. Indenestrol A (INDA) and indenestrol B (INDB) have nearly identical fully extended planar conformations. Either the a or y rings of these compounds may mimic the A ring of estradiol and compete for the estrogen receptor. Although there are eight distinct ways in which molecules of a racemic mixture of INDA or INDB can bind to the receptor, not all of them may be able to elicit a hormonal response. This may account for the reduced biological activity of the compounds despite their successful competition for receptor binding.The minimum energy conformations of Z-pseudodiethylstilbestrol (ZPD) and E-pseudodiethylstilbestrol (EPD) are bent in a fashion similar to that of indanestrol (INDC). These molecules have good binding affinity suggesting that the receptor does not require a flat molecule. Therefore these conformations would appear to be compatible with receptor binding, but only the Z isomer has an energetically allowed extended conformation that accounts for its observed biological activity relative to DES.

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Structure cristalline et moléculaire de l'oestradiol hemihydraté

Cited by 62 publications

References 4 publications

Novel Estradiol Derivatives Labeled with Ru, W, and Co Complexes. Influence on Hormone-Receptor Affinity of Several Organometallic Groups at the 17 Position

Novel Estradiol Derivatives Labeled with Ru, W, and Co Complexes. Influence on Hormone-Receptor Affinity of Several Organometallic Groups at the 17 Position

Structure of 4-fluoro-1,3,5(10)-estratriene-3,17β-diol–hemimethanol

Molecular conformation, receptor binding, and hormone action of natural and synthetic estrogens and antiestrogens.

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