Steroids derived from bile acids. Novel side-chain degradation scheme

Abstract

Chromatography of the residue on alumina, activity IV, and elution with benzene gave 40 mg of oily 12: ir (CC14) NH 3.18 (m), C=0 6.00 (s), C=C 6.32 µ (s). In view of its instability, it was used for the next reaction without further purification.A solution of 40 mg of 12 in 10 ml of 10% methanolic potassium hydroxide was stirred at room temperature under nitrogen for SO hr. It was neutralized with 10% hydrochloric acid and evaporated. Extraction of the residue with ethanol and evaporation of the extract gave lOmg of a viscous oil which crystallized slowly. Crystallization from ethyl acetate-ethanol yielded 4 mg of prisms of dZ-18,19-dihydroantirhine (5): mp 95-97.5°; infrared, ultraviolet, mass spectral, and tic characteristics identical with those of an authentic sample;6•18 m/e 298.204516 (caled 298.204503).Methyl Demethylilludinate ( 14).-A solution of dry potassium ¿erí-butoxide (from 620 mg of potassium) and 3.24 g of diester 7c in 25 ml oí 1,2-dimethoxyethane was added dropwise to 1.75 g of 3,3-dimethylcyclopentanone16 over a 1-hr period and the mixture was stirred at room temperature under nitrogen for 15 hr. Hydrochloric acid (50 ml of 3 N) was added and the mixture was evaporated at 50°to dryness. The residue was dried further in a vacuum desiccator for 12 hr and then dissolved in 50 ml of methanol saturated with hydrogen chloride gas. After

Spectroscopic methods and theoretical studies of bromoacetic substituted derivatives of bile acids

“…Steroids play also important functions in the regulation of metabolism (e.g., bile acids and vitamin D). [1][2][3][4] Especially important compounds are bile acids (e.g., lithocholic, deoxycholic and cholic) and their derivatives. The cholic acid was first isolated from the bile of mammals in 1828 by L. Gmelin.…”

Steroidal Conjugates: Synthesis, Spectroscopic, and Biological Studies

“…6.1). SCHEME 6.1 Biosynthesis of primary (6,7), secondary (4,5), and conjugated bile acids (4a-7b). They play a very important role in supramolecular chemistry and as drugs in pharmacology [16,17].…”

Synthesis, Spectroscopic and Semiempirical Studies of New Quaternary Alkylammonium Conjugates of Sterols

“…They are also the main sex hormones in mammals (e.g., testosterone and estrogens) and plants (e.g., brassinosteroids). They also regulate metabolism (e.g., glycocholic and taurocholic acid or vitamin D) and are important cardioactive glycosides (e.g., digoxin, gitoxin and scillaren A) [3][4][5][6]. Exceptionally interesting group of steroids are the sterols, e.g., cholesterol, cholestanol, ergosterol and stigmasterol [7][8][9].…”