Synthesis of imidazo[1,2-a]pyridines as antiviral agents

被引:217
作者
Gueiffier, A
Mavel, S
Lhassani, M
Elhakmaoui, A
Snoeck, R
Andrei, G
Chavignon, O
Teulade, JC
Witvrouw, M
Balzarini, J
De Clercq, E
Chapat, JP
机构
[1] Univ Tours, Fac Pharm, Chim Therapeut Lab, F-37200 Tours, France
[2] EA Pharmacochim & Biomol, Lab Chim Organ Pharmaceut, F-34060 Montpellier, France
[3] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
[4] UFR Pharm, Grp Rech Pharmacochim, Lab Chim Organ Pharmaceut, F-63001 Clermont Ferrand, France
关键词
D O I
10.1021/jm981051y
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of original imidazo[1,2-a]pyridines bearing a thioether side chain at the 3 position and their antiviral activity are reported. From the synthesized compounds, 4, 15, and 21 were highly active against human cytomegalovirus with a therapeutic index superior to 150. These compounds also showed pronounced activity against varicella-zoster virus. Their structure-activity relationship is discussed.
引用
收藏
页码:5108 / 5112
页数:5
相关论文
共 20 条
[1]  
Alford Charles A., 1993, P227
[2]   9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE (PMEA) EFFECTIVELY INHIBITS RETROVIRUS REPLICATION INVITRO AND SIMIAN IMMUNODEFICIENCY VIRUS-INFECTION IN RHESUS-MONKEYS [J].
BALZARINI, J ;
NAESENS, L ;
SLACHMUYLDERS, J ;
NIPHUIS, H ;
ROSENBERG, I ;
HOLY, A ;
SCHELLEKENS, H ;
DECLERCQ, E .
AIDS, 1991, 5 (01) :21-28
[3]  
BUUHOI NP, 1959, CR HEBD ACAD SCI, V248, P1832
[4]   Susceptibility of human cytomegalovirus to cidofovir is unchanged after limited in vivo exposure to various clinical regimens of drug [J].
Cherrington, JM ;
Miner, R ;
Hitchcock, MJM ;
Lalezari, JP ;
Drew, WL .
JOURNAL OF INFECTIOUS DISEASES, 1996, 173 (04) :987-992
[5]   COMPARATIVE EFFICACY OF ANTIHERPES DRUGS AGAINST DIFFERENT STRAINS OF HERPES-SIMPLEX VIRUS [J].
DECLERCQ, E ;
DESCAMPS, J ;
VERHELST, G ;
WALKER, RT ;
JONES, AS ;
TORRENCE, PF ;
SHUGAR, D .
JOURNAL OF INFECTIOUS DISEASES, 1980, 141 (05) :563-574
[6]   A NOVEL SELECTIVE BROAD-SPECTRUM ANTI-DNA VIRUS AGENT [J].
DECLERCQ, E ;
HOLY, A ;
ROSENBERG, I ;
SAKUMA, T ;
BALZARINI, J ;
MAUDGAL, PC .
NATURE, 1986, 323 (6087) :464-467
[7]  
DELCORONA L, 1981, FARMACO-ED SCI, V36, P994
[8]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3-SUBSTITUTED IMIDAZO[1,2-A]PYRIDINES [J].
ELHAKMAOUI, A ;
GUEIFFIER, A ;
MILHAVET, JC ;
BLACHE, Y ;
CHAPAT, JP ;
CHAVIGNON, O ;
TEULADE, JC ;
SNOECK, R ;
ANDREI, G ;
DECLERCQ, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (16) :1937-1940
[9]   THE OUTCOME OF CONGENITAL CYTOMEGALOVIRUS-INFECTION IN RELATION TO MATERNAL ANTIBODY STATUS [J].
FOWLER, KB ;
STAGNO, S ;
PASS, RF ;
BRITT, WJ ;
BOLL, TJ ;
ALFORD, CA .
NEW ENGLAND JOURNAL OF MEDICINE, 1992, 326 (10) :663-667
[10]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF 2-SUBSTITUTED AND 3-SUBSTITUTED IMIDAZO[1,2-ALPHA]PYRIMIDINE [J].
GUEIFFIER, A ;
BLACHE, Y ;
CHAPAT, JP ;
ELHAKMAOUI, A ;
ESSASSI, EM ;
ANDREI, G ;
SNOECK, R ;
DECLERCQ, E ;
CHAVIGNON, O ;
TEULADE, JC ;
FAUVELLE, F .
NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5) :551-554