Journal of Medicinal Chemistry p. 2210 - 2214 (1989)
Update date:2022-08-03
Topics:
Cannon
True
Long
Bhatnagar
Leonard
Flynn
On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substition pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.
View MoreHangzhou Reb Technology Co., Ltd.
Contact:571-81902596
Address:Room 502,Buil.5,No.1 Xi Yuan Rd. The West Lake Science&Technology Park, Hangzhou,Zhejiang,China.
website:http://www.sjc.com.tw
Contact:(886) 2-2396-6223
Address:14Fl., No. 99. Sec. 2, Jen Ai Road
website:http://www.chinaskyrun.com
Contact:0086-576-84610586
Address:Chemical Development Zone
Changzhou Medi-tech Bioscientific Co., Ltd.
Contact:86-519-83246372
Address:Number 115 Menghedadao Road, Changzhou, Jiangsu, China
Qingzhou Baibang import and export co.,Ltd
Contact:+86-536-3265899
Address:No.338, Tuoshan Road
Doi:10.1080/00397911.2013.783074
(2013)Doi:10.1002/anie.200906811
(2010)Doi:10.1021/ol100599c
(2010)Doi:10.1007/BF00480755
(1989)Doi:10.1021/op9003289
(2010)Doi:10.1007/s11426-013-4840-x
(2013)