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一锅法合成具有生物活性的 1,2,3-三取代的吡咯并[2,3-b]喹喔啉:通过钯催化的带有内部炔基部分的反应。

One-pot synthesis of biologically active 1,2,3-trisubstituted pyrrolo[2,3-b]quinoxalines through a palladium-catalyzed reaction with internal alkyne moieties.

机构信息

Faculty of Chemistry, Shahrood University of Technology, Shahrood, 36199-95161, Iran.

Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, Zanjan, 45137-66731, Iran.

出版信息

Mol Divers. 2018 Nov;22(4):879-891. doi: 10.1007/s11030-018-9838-z. Epub 2018 Jun 16.

Abstract

Synthesis of 2,3-disubstituted 1-alkylpyrrolo[2,3-b]quinoxalines was accomplished through the reaction of 3-chloroquinoxalin-2-amines with internal alkynes in the presence of Pd(OAc)[Formula: see text], NaOAc, and KOtBu in DMSO. This method afforded desired pyrrolo[2,3-b]quinoxalines in 65-92% reaction yields. The minimum inhibition concentration and minimum bactericidal concentration determinations against Micrococcus luteus and Pseudomonas aeruginosa revealed that some of the synthesized compounds showed the same values compared to tetracycline. These compounds could be used in the future research for the development of new antibiotics.

摘要

通过在 Pd(OAc)[化学式见文本]、NaOAc 和 KOtBu 的存在下,用 3-氯喹喔啉-2-胺与内部炔烃反应,合成了 2,3-二取代的 1-烷基吡咯并[2,3-b]喹喔啉。该方法以 65-92%的反应产率得到所需的吡咯并[2,3-b]喹喔啉。对金黄色葡萄球菌和铜绿假单胞菌的最低抑制浓度和最低杀菌浓度测定表明,一些合成化合物与四环素具有相同的数值。这些化合物可用于未来开发新抗生素的研究。

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