Synthesis of certain unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)-tricyclo[5.2.1.02,6]decane-8-ketoxime esters and ethers with local anesthetic and analgesic activities
摘要:
The synthesis of series of unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)tricyclo [5.2.1.0(2,6)]decane-8-ketoximes esters and ethers 3a-j, 3a-d, 7a-j and 13a-d from the oxime synthons 2, 6a-e, 12a and 12b, respectively, is described. All the obtained compounds displayed noticeable local anesthetic potential. Among them, the oximino ether 4d (ED50 = 0.15 mg/kg) and the oximino ester 3a (ED50 = 0.23 mg/kg) are the most active of the series and possess higher potential than the reference standards. Some of the target compounds evoked analgesic effect, specially the oximino ether 7i which is the most potent of the series and is stronger than acetylsalicylic acid but weaker than morphine hydrochloride. (C) 1998 Elsevier Science S.A. All rights reserved.
Stereoselective reactions. V. Design of the asymmetric synthesis of lignan lactones. Synthesis of optically active podorhizon and deoxypodorhizon by 1,3-asymmetric induction.
Stereoselective reactions. V. Design of the asymmetric synthesis of lignan lactones. Synthesis of optically active podorhizon and deoxypodorhizon by 1,3-asymmetric induction.
作者:KIYOSHI TOMIOKA、HIDEMICHI MIZUGUCHI、KENJI KOGA
DOI:10.1248/cpb.30.4304
日期:——
A novel method for the asymmetric synthesis of both enantiomers of 2, 3-disubstituted-butanolides (8) was devised using a readily available (S)-4-hydroxymethyl-4-butanolide 4-derivative (6) as a chiral source in the asymmetric induction and as the carbon framework of 8. Application of this method to the asymmetric total synthesis of podorhizon (23) and deoxypodorhizon (4) is described.
Compounds of the following formula ##STR1## are useful as central nervous system depressants, tranquilizers, sedatives, growth promotors, anti-convulsants and muscle relaxants in mammalian species.