Tetrahedron p. 4601 - 4608 (1987)
Update date:2022-08-05
Topics:
Ashwell, Mark
Jones, A. Stanley
Kumar, Ajit
Sayers, Jon R.
Walker, Richard T.
et. al.
A method for the synthesis of the potent anti-herpes agent, (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) (1) is described.A trace bye-product of the synthesis has been identified as 5-(1,2-dibromo-2-succinimidoethyl)-2'-deoxyuridine (5).A similar bye-product, 5-(1,2-dibromo-2-succinimidoethyl)uridine (4) is formed during the synthesis of (E)-5-(2-bromovinyl)uridine (3).The following derivatives of BVDU have been synthesised: 3'-O-methyl (8), 3-methyl (9), 4-O-ethyl (11), O2,5'-anhydro-(E)-5-(2-bromovinyl)-2'-deoxyuridine (13) and (E)-5-(2-bromovinyl)-2'-deoxyisocytidine (15).Whereas compounds 8, 9 and 15 showed little, if any, antiviral activity, 11 and, in particular, 13, were significantly active against herpes simplex virus type 1 and varicella-zoster virus.
View MoreZhenjiang Haitong Chemical Industry Co., Ltd.
Contact:+86 (511) 8448-0369
Address:Baoyan Town, Dantu District, Zhenjiang City, Jiangsu, China
Guangzhou PI & PI Biotech Inc. Ltd.
Contact:+86-20-81716320
Address:Suite 501,198 Kaiyuan Ave.,Science City, Guangzhou,China
Chongqing Werlchem Fine Chemical Co. Ltd
Contact:+86-23-67521957
Address:NO.15,Fortune Road,Yubei District,401121,Chongqing,China
Contact:86-371-63655023
Address:No.85,jinshui road,zhengzhou,China
Huaian Double Win Chemicals Co.,Ltd.
Contact:+86-13511538872
Address:Blk 43,Greenland Century Town,Huaian District, Huaian City,Jiangsu Province,China
Doi:10.1016/j.bmcl.2013.09.006
(2013)Doi:10.1021/ol402749s
(2014)Doi:10.1021/acs.joc.5b00139
(2015)Doi:10.1016/j.ejmech.2008.09.011
(2009)Doi:10.1248/cpb.35.3576
(1987)Doi:10.1016/j.bmcl.2009.01.047
(2009)