Short synthesis and anti-rhinoviral activity of imidazo[1,2-a]pyridines:: The effect of acyl groups at 3-position

被引：39

作者：

Hamdouchi, C

Ezquerra, J

Vega, JA

Vaquero, JJ

Alvarez-Builla, J

Heinz, BA

机构：

[1] Ctr Invest Lilly SA, Madrid 28108, Spain

[2] Univ Alcala de Henares, Dept Quim Organ, Madrid 28871, Spain

[3] Lilly Res Labs, Infect Dis Res, Indianapolis, IN 46285 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 10期

关键词：

D O I：

10.1016/S0960-894X(99)00193-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Various 2-amino-3-acyl-6-[(E)-1-phenyl-2-N-methylcarbamoylvinyl]-imidazo[1,2-a]pyridines, structurally related to Enviroxime were prepared to determine the effect of acyl groups on the anti-rhinoviral activity. A short and efficient means for the construction of the imidazo nucleus as well as biological evaluation of the final compounds are disclosed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1391 / 1394

页数：4

相关论文

共 10 条

[1] 2-amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imidazo-[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus:: Stereospecific synthesis and antiviral activity [J].

Hamdouchi, C ;

de Blas, J ;

del Prado, M ;

Gruber, J ;

Heinz, BA ;

Vance, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (01) :50-59

[2] THE ANTIVIRAL COMPOUND ENVIROXIME TARGETS THE 3A CODING REGION OF RHINOVIRUS AND POLIOVIRUS [J].

HEINZ, BA ;

VANCE, LM .

JOURNAL OF VIROLOGY, 1995, 69 (07) :4189-4197

[3] Sequence determinants of 3A-mediated resistance to enviroxime in rhinoviruses and enteroviruses [J].

Heinz, BA ;

Vance, LM .

JOURNAL OF VIROLOGY, 1996, 70 (07) :4854-4857

[4] CONTROLLED TRIAL OF ENVIROXIME AGAINST NATURAL RHINOVIRUS INFECTIONS IN A COMMUNITY [J].

MILLER, FD ;

MONTO, AS ;

DELONG, DC ;

EXELBY, A ;

BRYAN, ER ;

SRIVASTAVA, S .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1985, 27 (01) :102-106

[5]

PHILLPOTTS RJ, 1981, LANCET, V1, P1342

[6] VIRUCIDAL ACTIVITY OF HYPERICIN AGAINST ENVELOPED AND NONENVELOPED DNA AND RNA VIRUSES [J].

TANG, J ;

COLACINO, JM ;

LARSEN, SH ;

SPITZER, W .

ANTIVIRAL RESEARCH, 1990, 13 (06) :313-325

[7] Antirhino/enteroviral vinylacetylene benzimidazoles: A study of their activity and oral plasma levels in mice [J].

Tebbe, MJ ;

Spitzer, WA ;

Victor, F ;

Miller, SC ;

Lee, CC ;

Sattelberg, TR ;

McKinney, E ;

Tang, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3937-3946

[8] A new approach to the synthesis of 2-aminoimidazo[1,2-a]pyridine derivatives through microwave-assisted N-alkylation of 2-halopyridines [J].

Vega, JA ;

Vaquero, JJ ;

Alvarez-Builla, J ;

Ezquerra, J ;

Hamdouchi, C .

TETRAHEDRON, 1999, 55 (08) :2317-2326

[9] Synthesis and antiviral activity of C2 analogs of Enviroxime: An exploration of the role of critical functionality [J].

Victor, F ;

Loncharich, R ;

Tang, J ;

Spitzer, WA .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (21) :3478-3483

[10] SYNTHESIS OF SYN AND ANTI ISOMERS OF 6-[[(HYDROXYIMINO)PHENYL]METHYL]-1-[(1-METHYLETHYL)SULFONYL]-1H-BENZIMIDAZOL-2-AMINE - INHIBITORS OF RHINOVIRUS MULTIPLICATION [J].

WIKEL, JH ;

PAGET, CJ ;

DELONG, DC ;

NELSON, JD ;

WU, CYE ;

PASCHAL, JW ;

DINNER, A ;

TEMPLETON, RJ ;

CHANEY, MO ;

JONES, ND ;

CHAMBERLIN, JW .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (04) :368-372