Synthesis and antiherpetic activity of (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines

被引：0
|
作者：
A. V. Ivanov
V. L. Andronova
G. A. Galegov
M. V. Jasko
机构：
[1] Russian Academy of Sciences,Engelhardt Institute of Molecular Biology
[2] Russian Academy of Medical Sciences,Ivanovskii Institute of Virology
来源：
Russian Journal of Bioorganic Chemistry | 2005年 / 31卷
关键词：
herpes simplex virus; nucleotides; phosphonates;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
The isomeric (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines were synthesized. The stereoselectivity of double bond formation was studied by variation of sulfonyl groups. The resulting phosphonates exhibited a moderate antiherpetic activity in a culture of Vero cells infected with herpes simplex type 1 virus. The Z-isomer was shown to be a more effective inhibitor of virus reproduction in the case of both wild and acyclovir-resistant strains.
引用
收藏
页码：58 / 65
页数：7
相关论文
共 50 条
  • [1] Synthesis and antiherpetic activity of (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines
    Ivanov, AV
    Andronova, VL
    Galegov, GA
    Jasko, MV
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2005, 31 (01) : 58 - 65
  • [2] SYNTHESIS AND ANTIHERPETIC ACTIVITY OF (+/-)-9-[[(Z)-2-(HYDROXYMETHYL)CYCLOPROPYL]METHYL]GUANINE AND RELATED-COMPOUNDS
    ASHTON, WT
    MEURER, LC
    CANTONE, CL
    FIELD, AK
    HANNAH, J
    KARKAS, JD
    LIOU, R
    PATEL, GF
    PERRY, HC
    WAGNER, AF
    WALTON, E
    TOLMAN, RL
    JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) : 2304 - 2315
  • [3] The synthesis of an acyclic nucleotide analogue, (E)-9-(3-phosphonylmethoxypropen-1-yl)adenine
    Ivanov, AV
    Jasko, MV
    Skoblov, YS
    Kukhanova, MK
    CHEMISTRY OF NUCLEIC ACID COMPONENTS, 2002, 5 : 43 - 47
  • [4] (E)-9-(But-2-en-1-yl)-6-chloro-9H-purine
    Lundvall, Fredrik
    Kania, Jindrich
    Gundersen, Lise-Lotte
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O849 - +
  • [5] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 9-[4-HYDROXY-3-(HYDROXYMETHYL)BUT-1-YL]PURINES
    HARNDEN, MR
    JARVEST, RL
    BACON, TH
    BOYD, MR
    JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) : 1636 - 1642
  • [6] Fluoroanalogues of anti-cytomegalovirus agent cyclopropavir:: Synthesis and antiviral activity of (E)- and (Z)-9-{[2,2-bis(hydroxymethyl)-3-fluorocyclopropylidene]methyl}-adenines and guanines
    Zhou, Shaoman
    Zemlicka, Jiri
    Kern, Earl R.
    Drach, John C.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (03): : 231 - 243
  • [7] AN EFFICIENT SYNTHESIS OF 1,3(E),5(Z), 1,3(E),5(E) AND 1,3(Z),5(Z)-TRIENES - APPLICATION TO THE SYNTHESIS OF GALBANOLENES AND (9Z,11E)-9,11,13-TETRADECATRIEN-1-YL ACETATE
    ALAMI, M
    GUEUGNOT, S
    DOMINGUES, E
    LINSTRUMELLE, G
    TETRAHEDRON, 1995, 51 (04) : 1209 - 1220
  • [8] SYNTHESIS OF NEW 9-[3-(THYM-1-YL)PROPYL] PURINES
    WENSKA, G
    POLISH JOURNAL OF CHEMISTRY, 1981, 55 (05) : 1157 - 1161
  • [9] SYNTHESIS OF ANOMERIC 9-(2-DEOXY-1-D-GLUCOSYL)-ADENINES AND THEIR ANHYDRO DERIVATIVES
    NOVAK, JJK
    SORM, F
    EXPERIENTIA, 1962, 18 (05): : 213 - &
  • [10] Antiviral activity of [(Z)- and (E)-9-[3-(phosphonomethoxy)prop-1-en-1-purines] in cell cultures and evaluation of their diphosphates in cell-free system
    Kukhanova, M
    Ivanov, A
    Galegov, G
    Andronova, V
    Jasko, M
    ANTIVIRAL RESEARCH, 2006, 70 (01) : A86 - A86
12345