Synthesis of Azahelicenes via Friedel‐Crafts‐Type Ring‐Closing Reaction of Axially Chiral Compounds

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI:10.1002/ajoc.202400128
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Abstract

Aza[6]helicene and aza[7]helicene were synthesized by Fridel‐Crafts‐type cyclization of axially chiral compounds. From the axially chiral compounds prepared by Fischer indole synthesis, aza[6]helicene and aza[7]helicene were synthesized. Aza[7]helicene was also synthesized from an axially chiral pyrrole compound prepared by Piloty‐Robinson‐type pyrrole synthesis through simultaneous cyclization on both sides of the pyrrole ring. Aza[6]helicene isomerized readily at room temperature, while aza[7]helicene isomerization at room temperature was less likely to proceed. The cell growth inhibitory activity of each enantiomer of N‐Me‐aza[7]helicene in HeLa cells was examined. Differences in the strength of activity between the enantiomers were observed.

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通过轴向手性化合物的 Friedel-Crafts 型闭环反应合成氮杂环烯
通过对轴向手性化合物进行 Fridel-Crafts 型环化,合成了氮杂[6]螺旋烯和氮杂[7]螺旋烯。从费舍尔吲哚合成法制备的轴手性化合物中合成出了氮杂[6]螺旋烯和氮杂[7]螺旋烯。此外,还利用 Piloty-Robinson 型吡咯合成法制备的轴手性吡咯化合物,通过吡咯环两侧的同时环化合成了氮杂[7]螺旋烯。氮杂[6]螺旋烯在室温下很容易异构化,而氮杂[7]螺旋烯在室温下异构化的可能性较小。研究了 N-Me-aza[7]helicene对映体在 HeLa 细胞中的细胞生长抑制活性。观察到对映体之间的活性强度存在差异。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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