Quantitative relationships between steroid structure and binding to putative progesterone receptors

Relationships between chemical structure of androst-4-en-3-one derivatives and their affinity for putative progesterone receptors are described. The binding affinity for 55 derivatives can be expressed by the equation log relative binding affinity (rabbit receptor) = 1.79 + 0.18 (+/-0.11) pia + 1.45...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1977-09, Vol.20 (9), p.1139-1146
Main Authors: Lee, D L, Kollman, P A, Marsh, F J, Wolff, M E
Format: Article
Language:English
Subjects:
Androstenes
Animals
Guinea Pigs
Humans
Hydroxyprogesterones
Protein Binding
Rabbits
Receptors, Progesterone - metabolism
Sheep
Steroids - metabolism
Structure-Activity Relationship
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Summary:Relationships between chemical structure of androst-4-en-3-one derivatives and their affinity for putative progesterone receptors are described. The binding affinity for 55 derivatives can be expressed by the equation log relative binding affinity (rabbit receptor) = 1.79 + 0.18 (+/-0.11) pia + 1.45 (+/-0.21) pib + 0.010 (+/-0.002) (surface area in hydrophobic pockets) - 0.012 (+/-0.003) (surface area out of hydrophobic pockets) - 0.99 (+/-0.21) MK - 0.33 (+/-0.08) (conformational changes). For this equation, r=0.88. The equation successfully predicts the affinities of other compounds in the literature. The importance of the surface area terms is discussed.
ISSN:0022-2623
DOI:10.1021/jm00219a006