Synthesis and biological activities of new furo(3,4-b)carbazoles: potential topoisomerase II inhibitors.

Hajbi Y; Neagoie C; Biannic B; Chilloux A; Vedrenne E; Baldeyrou B; Bailly C; Merour JY; Rosca S; Routier S; Lansiaux A

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Synthesis and biological activities of new furo(3,4-b)carbazoles: potential topoisomerase II inhibitors.

机译：新呋喃（3,4-B）咔唑的合成和生物活性：潜在的拓扑异构酶II抑制剂。

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New 1,5-dihydro-4-(substituted phenyl)-3H-furo[3,4-b]carbazol-3-ones were synthesised via a key step Diels-Alder reaction under microwave irradiation. 3-Formylindole was successfully used in a 6-step synthesis to obtain those complex heterocycles. The Diels-Alder reaction generating the carbazole ring was optimised under thermal conditions or microwave irradiation. After cleavage of functional groups, DNA binding, topoisomerase inhibition and cytotoxic properties of the new-formed furocarbazoles were investigated. These carbazoles do not present a strong interaction with the DNA, and do not modify the relaxation of the DNA in the presence of topoisomerase I or II except for one promising compound. This compound is a potent topoisomerase II inhibitor, and its cellular activity is not moderated compared to etoposide. The synthesis of these molecules allowed the generalisation of the method using indole and 5-OBn indole and several benzaldehydes. The synthesis of these molecules produced chemical structures endowed with promising cytotoxic and topoisomerase II inhibition activities.

机译：通过微波辐射下的关键步骤Diels-Alder反应合成了新的1,5-二氢-4-（取代的苯基）-3H-Furo [3,4-B]咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3- 3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔唑-3-咔咔。在6步合成中成功地使用3-甲酰基吲哚，得到这些复合物杂环。在热条件或微波辐射下优化产生咔唑环的DIELS-桤木反应。研究了官能团的裂解后，研究了新型呋喃脲的DNA结合，拓扑异构酶抑制和细胞毒性特性。这些咔唑不存在与DNA的强相互作用，除了一个有希望化合物之外，在外甲基异构酶I或II的存在下，不会改变DNA的松弛。该化合物是有效的拓扑异构酶II抑制剂，与依托泊苷相比，其细胞活性未进行调节。这些分子的合成允许使用吲哚和5-OBN吲哚和几种苯甲醛的方法的概括。这些分子的合成产生了具有有前途的细胞毒性和拓扑异构酶II抑制活性的化学结构。

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《European Journal of Medicinal Chemistry: Chimie Therapeutique》 |2010年第11期|共10页
作者
Hajbi Y; Neagoie C; Biannic B; Chilloux A; Vedrenne E; Baldeyrou B; Bailly C; Merour JY; Rosca S; Routier S; Lansiaux A;
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Institut de Chimie Organique et Analytique Universite d'Orleans CNRS UMR 6005 B.P. 6759 45067 Orleans Cedex 2 France.;

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1. Synthesis and biological activities of new furo(3,4-b)carbazoles: potential topoisomerase II inhibitors. [J] . Hajbi Y, Neagoie C, Biannic B, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2010,第11期

机译：新型呋喃（3,4-b）咔唑的合成和生物活性：潜在的拓扑异构酶II抑制剂。
2. Synthesis and biological activities of new furo(3,4-b)carbazoles: potential topoisomerase II inhibitors. [J] . Hajbi Y, Neagoie C, Biannic B, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2010,第11期

机译：新呋喃（3,4-B）咔唑的合成和生物活性：潜在的拓扑异构酶II抑制剂。
3. Synthesis and biological activities of new furo(3,4-b)carbazoles: potential topoisomerase II inhibitors. [J] . Hajbi Y, Neagoie C, Biannic B, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2010,第11期

机译：新呋喃（3,4-B）咔唑的合成和生物活性：潜在的拓扑异构酶II抑制剂。
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6. Treatment with inhibitors of polyamine biosynthesis which selectively lower intracellular spermine does not affect the activity of alkylating agents but antagonizes the cytotoxicity of DNA topoisomerase II inhibitors. [O] . M. A. Desiderio, D. Bergamaschi, E. Mascellani, 1997

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机译：含氟杂环：第III部分。一些具有预期生物活性的新型呋喃并[2,3-b] - ，吡唑并[3,4-b] - 和噻吩并[2,3-b]吡啶的合成

Synthesis and biological activities of new furo(3,4-b)carbazoles: potential topoisomerase II inhibitors.

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