Journal of Medicinal Chemistry p. 625 - 629 (1989)
Update date:2022-08-04
Topics:
Norbeck, Daniel W.
Rosenbrook, William
Kramer, James B.
Grampovnik, David J.
Lartey, Paul A.
Although 8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonic acid (2) is a potent inhibitor of 3-deoxy-D-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase), it is unable to reach its cytoplasmic target and is therefore inactive as an antibacterial agent.However, esterification of 2 with 8-(hydroxymethyl)-1-naphthyl methyl disulfide (8) generates a prodrug (12), which gains entry into bacterial cells.Intracellular reduction of the disulfide leads to a rapid, intramolecular, displacement of the acid 2, which then inhibits the growth of Gram-negative bacteria by interfering with the biosynthesis of lipopolysaccharide.
View MoreZhengzhou Institute of Chiral Pharmer Research Co., Ltd.
Contact:86-371-55219111
Address:15 Floor, 2 Building, Central China Technovalley, Zhongyuan West Road
Linyi Shengxin Pharmaceutical R&D Co., Ltd
Contact:+86-18653953873
Address:West First of Yufeng Road, Yishui County
website:http://www.hope-chem.com
Contact:86-21-58090396-805
Address:Floor 4, Building 5, No.588 Tianxiong Road, Zhoupu International Medical Zone, ShangHai, China
Contact:+1 (647) 918 5848
Address:2343 BRIMLEY RD., Suite 250
Engineering Research Center of Pesticide, Heilongjiang Province
Contact:+86-451-86609001
Address:No.74 of Xuefu Road, Nangang District,
Doi:10.1021/jo026086r
(2002)Doi:10.1016/j.bmc.2015.02.028
(2015)Doi:10.1021/np900464p
(2009)Doi:10.1002/jhet.82
(2009)Doi:10.1002/ejoc.200900055
(2009)Doi:10.1055/s-0029-1216851
(2009)
