Cardiac glycoside-like structure and function of 5 beta,14 beta-pregnanes
Journal Article
·
· Journal of Medicinal Chemistry; (USA)
5 beta-Reduction and 14 beta-substitution convert the planar progesterone molecule to the cardiac glycoside configuration--A and D rings of the steroid moiety are bent toward the alpha-face relative to the B and C rings. Potency of the 5 beta,14 beta-derivative in a ({sup 3}H)ouabain binding assay or its ability to inhibit the sodium pump in red blood cells is enhanced by 3 beta-hydroxylation, 20 beta-hydroxylation, and 3 beta-glycosidation. Synthesis of 14,20 beta-dihydroxy-3 beta-(beta-D-glucopyranosyloxy)- 5 beta,14 beta-pregnane from digitoxin is described. The glucoside is 1/20 as potent as ouabain and elicits prominent, sustained, positive inotropy in isolated cardiac muscle.
- OSTI ID:
- 5478913
- Journal Information:
- Journal of Medicinal Chemistry; (USA), Journal Name: Journal of Medicinal Chemistry; (USA) Vol. 32:8; ISSN JMCMA; ISSN 0022-2623
- Country of Publication:
- United States
- Language:
- English
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OSTI ID:5921814
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OSTI ID:7070114
Related Subjects
550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANIMALS
BIOLOGICAL FUNCTIONS
BIOLOGICAL MATERIALS
BLOOD
BLOOD CELLS
BODY
BODY FLUIDS
CARBOHYDRATES
CARDIAC GLYCOSIDES
CARDIOTONICS
CARDIOVASCULAR AGENTS
CARDIOVASCULAR SYSTEM
DOGS
DRUGS
ERYTHROCYTES
FUNCTIONS
GLYCOSIDES
HEART
HYDROGEN COMPOUNDS
IN VITRO
ISOTOPE APPLICATIONS
MAMMALS
MAN
MATERIALS
MEMBRANE PROTEINS
MOLECULAR STRUCTURE
MUSCLES
ORGANIC COMPOUNDS
ORGANS
OUABAIN
PREGNANES
PRIMATES
PROTEINS
RECEPTORS
STEROIDS
STROPHANTHINS
STRUCTURE-ACTIVITY RELATIONSHIPS
TRACER TECHNIQUES
TRITIUM COMPOUNDS
VERTEBRATES
59 BASIC BIOLOGICAL SCIENCES
ANIMALS
BIOLOGICAL FUNCTIONS
BIOLOGICAL MATERIALS
BLOOD
BLOOD CELLS
BODY
BODY FLUIDS
CARBOHYDRATES
CARDIAC GLYCOSIDES
CARDIOTONICS
CARDIOVASCULAR AGENTS
CARDIOVASCULAR SYSTEM
DOGS
DRUGS
ERYTHROCYTES
FUNCTIONS
GLYCOSIDES
HEART
HYDROGEN COMPOUNDS
IN VITRO
ISOTOPE APPLICATIONS
MAMMALS
MAN
MATERIALS
MEMBRANE PROTEINS
MOLECULAR STRUCTURE
MUSCLES
ORGANIC COMPOUNDS
ORGANS
OUABAIN
PREGNANES
PRIMATES
PROTEINS
RECEPTORS
STEROIDS
STROPHANTHINS
STRUCTURE-ACTIVITY RELATIONSHIPS
TRACER TECHNIQUES
TRITIUM COMPOUNDS
VERTEBRATES