异吲哚酮核糖核苷的合成与抗病毒评估
Synthesis and antiviral evaluation of isatin ribonucleosides.
作者信息
de Oliveira Mara R P, Torres José C, Garden Simon J, dos Santos Carla Veronica B, Alves Thatyana Rocha, Pinto Angelo C, Pereira Helena de S, Ferreira Luiz Roberto Leão, Moussatché Nissin, Frugulhetti Izabel Christina de P P, Ferreira Vitor F, de Souza Maria Cecília B V
机构信息
Universidade Federal do Rio de Janeiro, Instituto de Química, Departamento de Química Orgânica, Ilha do Fundão, CEP 21945-970, Rio de Janeiro, Brazil.
出版信息
Nucleosides Nucleotides Nucleic Acids. 2002 Nov-Dec;21(11-12):825-35. doi: 10.1081/NCN-120016510.
A series of novel substituted isatin ribonucleosides 3b-3f were synthesized in good yields by a TMSOTf catalysed coupling reaction between the silylated nitrogenated base (1b-1f) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (2). Isatin nucleoside 3a previously reported was also prepared using this method giving high yield. From the compounds tested, ribonucleoside 3f proved to be the most active one when assayed for antiviral activitiy on HSV-1 infected cells, leading to 66% of inhibition of virus yield. All the isatin derivatives tested did not inhibit HIV-1 Reverse Transcriptase (RT) activity.
通过三甲基硅基三氟甲磺酸酯（TMSOTf）催化的硅烷基化含氮碱基（1b - 1f）与1 - O - 乙酰基 - 2,3,5 - 三 - O - 苯甲酰基 - β - D - 呋喃核糖（2）之间的偶联反应，以良好的产率合成了一系列新型取代异吲哚酮核糖核苷3b - 3f。先前报道的异吲哚酮核苷3a也采用此方法制备，产率很高。在所测试的化合物中，核糖核苷3f在对单纯疱疹病毒1型（HSV - 1）感染细胞进行抗病毒活性测定时被证明是最具活性的，导致病毒产量抑制率达66%。所有测试的异吲哚酮衍生物均未抑制HIV - 1逆转录酶（RT）活性。
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