17.alpha.-Ethyl-20.alpha.- and -20.beta.-dihydroprogesterones and other 17.alpha.-ethyl-substituted pregnanes as potential contragestational agents

Kanojia, Ramesh M.; Ostrowski, Paul; Hahn, Do Won; Allen, George P.; McGuire, J.L.

doi:10.1021/jm00245a020

Cited by 6 publications

(1 citation statement)

References 3 publications

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“…* The C,-interdistance for the progesterone/5-aH-androstane-3-one superposition was erroneously indicated as 1.074 A instead of 0.074 A in the previous note [lo]. 25 25 25 25 25 23 24 22 25 25 25 22 25 22 25 25 24 22 25 25 27 25 25 25 25 22 22 22 25 25 25 25 25 25 25 25 25 25 25 22 22 27 22 25 25 21 were obtained for the series of N = 55 progesterone derivatives of Table 2: 4,5,9,11,28,29,31,32,37,38 j ( E = -…”

Section: No Steroid Designation Acxpmentioning

confidence: 73%

Structure‐activity Relations in Gestagenic Steroids by the MTD Method. The Case of Hard Molecules and Soft Receptors

Simon

Bohl²

1992

Quant. Struct.‐Act. Relat.

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A QSAR is obtained for affinity towards the gestagenic receptor for a series of 55 progesterone derivatives (r = 0.935), using the MTD‐method, with MTD for steric misfit and f a corrected relative hydrophobicity. Acceptable stability of regression coefficients of vertex attributions are obtained when this QSAR is compared with previous QSAR's for a reduced series of progesterone derivatives and for testosterone derivatives. Acceptable predicted activities for test molecules (r2 = 0.71) and acceptable results in a cross validation‐like procedure (r2 = 0.76) were obtained. These are strong arguments that our MTD results correspond to some real features of the gestagenic receptor site. In order to explain relative success of the MTD‐method in QSAR's for steroids, as compared to other methods, molecular aspects of the receptor‐effector interaction are discussed in relation to QSAR‐methodology. Recent computational chemistry approaches are based upon drug molecule‐receptor site energy calculations, assuming a fixed conformation for the receptor site. If the drug molecules are “hard” (rigid), the steric misfit with a “soft” (conformationally flexible) receptor site may be avoided by induction of different local conformational changes in the latter.

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Section: No Steroid Designation Acxpmentioning

confidence: 73%