Journal of Medicinal Chemistry p. 1558 - 1566 (1988)
Update date:2022-08-04
Topics:
Smith, Roger A.
White, Robert L.
Krantz, Allen
The kinetics of inactivation of mitochondrial monoamine oxidase type B (MAO-B) by a series of 18 stereoisomers of tertiary α-allenic amines have been investigated in detail.The chirality of the allene group in N-methyl-N-aralkylpenta-2,3-dienamines was found to have a profound effect on the inactivation rate, with the (R)-allenes being up to 200-fold more potent than their (S)-allenic counterparts.The ability of (S)-allenes to inactivate MAO was severely compromised by the presence of N-phenethyl or N-α-substituted-aralkyl substituents.The opposing chiralities in both the allene and aralkyl groups of (R,R)- and (S,S)-N-methyl-N-(1,2,3,4-tetrahydro-1-naphthyl)-penta-2,3-dieneamine resulted in a difference of more than 3 oredrs of magnitude in inactivation rates.The stereoselectivity of MAO-B was examined further with a series of reversible aralkylamine inhibitors; thus (R)-1,2,3,4-tetrahydro-1-naphthylamine was determined to be 150-fold more potent than its enantiomer.
View MoreChengdu Gelipu Biotechnology Co., Ltd.
website:http://www.glp-china.com
Contact:86-28-82610909
Address:chegndu
Chongqing Werlchem Fine Chemical Co. Ltd
Contact:+86-23-67521957
Address:NO.15,Fortune Road,Yubei District,401121,Chongqing,China
Guilin Zhenda Bio-Tech Co., Ltd.
Contact:86-773-3568977
Address:-Yangtang shangshui industry park, Lingui county,
website:http://www.konochem.com
Contact:86-29-86107037-8015
Address:No.11 Daqing Road,Lianhu District,Xi’an 710082,China
Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd
website:http://www.jlpharms.com
Contact:+86-571-86982636
Address:Rm A606, Fuyi Center, jianqiao street, Jianggan Area
Doi:10.1039/c39860000515
(1986)Doi:10.1007/BF00515355
(1983)Doi:10.1002/hlca.19520350130
(1952)Doi:10.1139/V05-236
(2006)Doi:10.1002/hc.20589
(2010)Doi:10.1021/om00084a010
(1984)