NEUROSTEROID ANALOGS - PART 5 - ENANTIOMERS OF NEUROACTIVE STEROIDS AND BENZ[E]INDENES - TOTAL SYNTHESIS, ELECTROPHYSIOLOGICAL EFFECTS ON GABA(A) RECEPTOR FUNCTION AND ANESTHETIC ACTIONS IN TADPOLES

The synthesis of (3 beta,5 beta,8 alpha,9 beta,10 alpha,13 alpha,14 be ta,17 alpha)-3-hydroxypregnan-20-one 2, (3 beta,5 beta,8 alpha,9 beta, 10 alpha,13 alpha, 14 beta, 17 alpha)-3-hydroxyandrostane-17-carbonitr ile 4,dagger [3R-(3 alpha,3a alpha,5a beta,7 alpha,9a alpha,9b beta)]- 1-[dodecahydro-7-(2-hydroxyethyl)-3a-methyl 1H-benz[e]inden-3-yl]ethan one 6 and [3R-(3 alpha,3a alpha,5a beta,7 alpha,9a alpha,9b beta)]-dod ecahydro oxyethyl)3a-methyl-1H-benz[e]indene-3-carbonitrile 8 is repor ted.double dagger Steroids 2 and 4 have been used previously to invest igate the enantioselectivity of steroid action on GABA(A) receptor fun ction and to correlate steroid action at this receptor with the anesth etic actions of the compounds, The enantioselective actions of benz[e] indenes 6 and 8 have been evaluated for the same reasons in this study , Similar correlations between the enantioselective effects of both cl asses of compounds on GABA(A) receptor function and anesthetic potency in tadpoles have been observed.