阿昔洛韦和更昔洛韦的6-(4-联苯基)-3,9-二氢-9-氧代-5H-咪唑并[1,2-a]嘌呤类似物的合成及荧光性质

Synthesis and fluorescent properties of 6-(4-biphenylyl)-3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine analogues of acyclovir and ganciclovir.

作者信息

Goslinski Tomasz, Wenska Grazyna, Golankiewicz Bozenna, Balzarini Jan, De Clercq Erik

机构信息

Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):911-4. doi: 10.1081/NCN-120022684.

DOI:10.1081/NCN-120022684

PMID:14565309

Abstract

Tricyclic (T) analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2) carrying the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system [i.e., 6-(4-BrPh)TACV, 5 and 6-(4-BrPh)TGCV, 6] were transformed into 6-[(4'-R2)-4-biphenylyl] derivatives of TACV (7-9) and TGCV (10-12) by Suzuki cross coupling with 4-substituted phenylboronic acids. Compound 11 (R2 = CH2OH) showed a high (approximately 1000) selectivity index against herpes simplex virus type 1 (HSV-1) together with advantageous fluorescence properties (emission in visible region, little overlap with absorption and moderate intensity).

摘要

携带3,9-二氢-9-氧代-5H-咪唑并[1,2-a]嘌呤系统的阿昔洛韦（ACV，1）和更昔洛韦（GCV，2）的三环（T）类似物[即6-(4-溴苯基)TACV，5和6-(4-溴苯基)TGCV，6]通过与4-取代苯硼酸的铃木交叉偶联反应转化为TACV（7-9）和TGCV（10-12）的6-[(4'-R2)-4-联苯基]衍生物。化合物11（R2 = CH2OH）对单纯疱疹病毒1型（HSV-1）表现出高（约1000）选择性指数以及有利的荧光性质（在可见光区域发射，与吸收的重叠小且强度适中）。