Archiv der Pharmazie p. 487 - 495 (1995)
Update date:2022-08-02
Topics:
Wunsch
Zott
Hofner
Bauschke
Mitsunobu inversion of the (S)-configurated lactate (S)-7, which is prepared in four steps starting from (S)-tyrosine, leads to the (R)-configurated lactate (R)-7. The key step in the transformation of the enantiomeric lactates (S)-7 and (R)-7 into the benzomorphan analogous tricycles (R,S)-16a,b, (S,R)-16a,b, (S,S)-22, and (R,R)-22 is an intramolecular Oxa-Rictet-Spengler reaction: The amides (S)-13, (R)-13, (S)-19 and (R)-19, in which the carbonyl moiety - masked as an acetal - is linked to the 2-phenylethanol moiety, are cyclized to give the tricyclic amides (R,S)-15, (S,R)-15, (S,S)-21, and (R,R)-21, respectively. In a concentration of 100 μM both enantiomers of 16a, 16b, and 22 are not able to compete with 3H-(+)-MK 801 for the phencyclidine binding sites of NMDA receptors. In vivo, only (R,S)-16b and (S,S)-22 exhibit weak sedative and analgesic activity.
View MoreContact:+86-710-3516804
Address:Number 83,Panggong road,Xiangcheng District,Xiangyang ,Hubei
JiangXi Keyuan Biopharma Co., LTD.
Contact:+86-563-6833666
Address:Guangde Fine Chemical Zone, Anhui Province, China
Shanghai WinTide BioTechnology Co.,Ltd
Contact:86-21-37100630
Address:No. 908 Yunhe Road, Fengxian district, Shanghai
Shenzhen ZheYi Chemicals Co.,LTD(Shanghai Branch)
Contact:+86-21-54159691
Address:Room1002,Building No.2, Lane 98 Bixiu Road,Minhang District, Shanghai,China 201100
Qingdao XinYongAn Chemicals Co., Ltd
Contact:+86-532-81107967
Address:Chengyang dual-port industrial park by the sea,Qingdao
Doi:10.1016/j.steroids.2010.12.013
(2011)Doi:10.1002/adsc.200700340
(2008)Doi:10.1016/S0040-4039(97)00859-9
(1997)Doi:10.1016/j.tet.2016.02.044
(2016)Doi:10.1246/cl.141061
(2015)Doi:10.1016/S0040-4020(97)10042-4
(1997)