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肌苷酸脱氢酶抑制剂。2-取代肌苷酸

Inhibitors of inosinic acid dehydrogenase. 2-Substituted inosinic acids.

作者信息

Wong C G, Meyer R B

出版信息

J Med Chem. 1984 Apr;27(4):429-32. doi: 10.1021/jm00370a003.

DOI:10.1021/jm00370a003
PMID:6142953
Abstract

A series of 2-substituted inosine monophosphate (IMP) and inosine derivatives were synthesized and tested for inhibitory activity against IMP dehydrogenase from Escherichia coli. All of the IMP analogues that possessed electron-withdrawing substituents on the phenyl ring of a benzylthio group placed at the 2-position of IMP showed strong inhibition, which was competitive with IMP. No evidence of hydrophobic interactions of the 2-substituent with the enzyme was observed.

摘要

合成了一系列2-取代的肌苷一磷酸(IMP)和肌苷衍生物,并测试了它们对大肠杆菌IMP脱氢酶的抑制活性。所有在IMP 2位的苄硫基苯环上带有吸电子取代基的IMP类似物均表现出强烈的抑制作用,且与IMP具有竞争性。未观察到2-取代基与该酶存在疏水相互作用的证据。

相似文献

1
Inhibitors of inosinic acid dehydrogenase. 2-Substituted inosinic acids.肌苷酸脱氢酶抑制剂。2-取代肌苷酸
J Med Chem. 1984 Apr;27(4):429-32. doi: 10.1021/jm00370a003.
2
Inhibition of inosinic acid dehydrogenase by 8-substituted purine nucleotides.8-取代嘌呤核苷酸对次黄苷酸脱氢酶的抑制作用。
J Med Chem. 1981 Oct;24(10):1155-61. doi: 10.1021/jm00142a007.
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Affinity chromatography on immobilised nucleotides. The synthesis, specificity and applications of immobilised inosine 5'-monophosphate.固定化核苷酸亲和层析。固定化5'-肌苷单磷酸的合成、特异性及应用。
Eur J Biochem. 1980 Sep;110(1):279-88. doi: 10.1111/j.1432-1033.1980.tb04866.x.
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Inhibition of inosine monophosphate dehydrogenase (IMPDH) by the antiviral compound, 2-vinylinosine monophosphate.抗病毒化合物2-乙烯基肌苷单磷酸对肌苷单磷酸脱氢酶(IMPDH)的抑制作用
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Active-site modification of native and mutant forms of inosine 5'-monophosphate dehydrogenase from Escherichia coli K12.来自大肠杆菌K12的肌苷5'-单磷酸脱氢酶天然形式和突变形式的活性位点修饰
Biochem J. 1980 Nov 1;191(2):533-41. doi: 10.1042/bj1910533.
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Inosine 5'-monophosphate dehydrogenase of Escherichia coli. Purification by affinity chromatography, subunit structure and inhibition by guanosine 5'-monophosphate.大肠杆菌的肌苷5'-单磷酸脱氢酶。通过亲和色谱法纯化、亚基结构及受鸟苷5'-单磷酸的抑制作用
Biochem J. 1979 Dec 1;183(3):481-94. doi: 10.1042/bj1830481.
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[Ribonucleoside-5'-monophosphates with disubstituted phosphate residue do not interact with human inosine monophosphate dehydrogenase].具有二取代磷酸残基的核糖核苷-5'-单磷酸不与人肌苷单磷酸脱氢酶相互作用。
Bioorg Khim. 1997 Jan;23(1):42-5.
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Inhibition of inosine monophosphate dehydrogenase (IMPDH) by 2-[2-(Z)-fluorovinyl]inosine 5'-monophosphate.2-[2-(Z)-氟乙烯基]肌苷5'-单磷酸对肌苷单磷酸脱氢酶(IMPDH)的抑制作用
Bioorg Med Chem Lett. 2003 Feb 24;13(4):645-7. doi: 10.1016/s0960-894x(02)01053-3.
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Inhibition of inosine monophosphate dehydrogenase by sesquiterpene lactones.倍半萜内酯对肌苷单磷酸脱氢酶的抑制作用。
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Inosine 5'-monophosphate dehydrogenase of Escherichia coli K12: the nature of the inhibition by guanosine 5'-monophosphate.大肠杆菌K12的5'-肌苷酸脱氢酶:5'-鸟苷酸的抑制性质
Biochem J. 1973 Jul;133(3):607-8. doi: 10.1042/bj1330607.

引用本文的文献

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Synthesis and anti-Hantaan virus activity of N(1)-3-fluorophenyl-inosine.N(1)-3-氟苯基-肌苷的合成及其抗汉坦病毒活性
Antiviral Res. 2009 Jul;83(1):80-5. doi: 10.1016/j.antiviral.2009.03.007. Epub 2009 Apr 2.
2
IMP dehydrogenase: structure, mechanism, and inhibition.肌苷酸脱氢酶:结构、机制与抑制作用
Chem Rev. 2009 Jul;109(7):2903-28. doi: 10.1021/cr900021w.