C5-Morpholinomethylation of N1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction†,Organic & Biomolecular Chemistry

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C5-Morpholinomethylation of N1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-03-15 00:00:00 , DOI: 10.1039/c8ob00253c
Josipa Matić _{1,

2,

3,

4,

5} , Irena Nekola _{4,

5,

6} , Aleksandar Višnjevac _{3,

4,

7,

8,

9} , Renata Kobetić _{1,

2,

3,

4,

5} , Irena Martin-Kleiner _{3,

4,

5,

10,

11} , Marijeta Kralj _{3,

4,

5,

10,

11} , Biserka Žinić _{1,

2,

3,

4,

5}

Affiliation

A fast and efficient route for the introduction of a methylene bridged-amine (morpholinomethyl) functionality in the C5 position of the sulfonylated cytosine nucleobase has been developed. First, novel N1-sulfonylcytosine derivatives 3–6 were prepared by the condensation of silylated cytosine with selected sulfonyl chlorides. They were subsequently transformed to 5-morpholinomethyl-N1-sulfonylcytosine derivatives (8, 12–15) using microwave irradiation. As a result of cytosine ring opening in N1-tosylcytosine, depending on the reaction conditions, peculiar tosyl-urea derivative 9 has been isolated, which provided additional insight into the reaction pathway. The influence of the C5-substituent on the antiproliferative activity has been evaluated by performing the MTT test on U251, MCF-7 and MOLT-4 tumor cell-lines.

中文翻译：

一锅微波辅助曼尼希反应对N 1-磺酰基胞嘧啶的C5-Morpholinomethylation †

已经开发了在磺酰化胞嘧啶核苷碱基的C5位引入亚甲基桥接胺（吗啉代甲基）官能团的快速有效途径。首先，通过将甲硅烷基化的胞嘧啶与选定的磺酰氯缩合制备新的N 1-磺酰基胞嘧啶衍生物3-6。他们随后被转化成5- morpholinomethyl- Ñ 1- sulfonylcytosine衍生物（8，12-15使用微波辐射）。由于N 1-tosylcytosine中的胞嘧啶开环，根据反应条件，异戊糖脲衍生物9已分离，这提供了对反应途径的进一步了解。通过对U251，MCF-7和MOLT-4肿瘤细胞系进行MTT试验，可以评估C5取代基对抗增殖活性的影响。

更新日期：2018-03-15

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