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Pyranoindole compounds are a class of heterocyclic frameworks formed by the pyran and indole rings via various fusion modes. These structures are widely distributed in natural products derived from plants， fungi， and marine organisms. Owing to their unique electronic distributions， diverse fusion patterns， and abundant reactive sites， pyranoindoles exhibit a broad spectrum of biological activities， including anti-inflammatory， antibacterial， antitumor， and antiviral effects. Therefore， they have become a significant focus of research in medicinal chemistry. This review systematically summarizes the recent progress in the synthesis and biological evaluation of pyranoindole derivatives over the past decade， with a particular emphasis on classification according to the different fusion sites of the pyran and indole rings， such as [2，3-b]， [3，4-b]， [4，3-b]， [3，2-b]， [2，3-e]， [3，2-e]， and [2，3-g]. A diverse range of synthetic strategies has been developed. These include DABCO-catalyzed tandem Michael–Knoevenagel and oxa-Michael cyclization sequences， bifunctional squaramide-catalyzed Michael addition/cyclization， palladium-catalyzed decarboxylative cycloaddition enabling the dearomatization of 3-nitroindoles， iodine-promoted one-pot three-component reactions， electrochemical dual-oxidation cycloadditions， rhodium-catalyzed C-H activation and dual oxygen-coordinated annulations， graphene oxide-catalyzed tandem reactions in both organic and aqueous media， and BaTiO3 nanoparticle-assisted ultrasonic one-pot syntheses. Each strategy offers distinct advantages in terms of the substrate scope， stereocontrol， atom economy， and environmental compatibility. These methods have enabled the efficient assembly of structurally diverse pyranoindole scaffolds， including spirocyclic， tetracyclic， and fluorinated derivatives， with high yields and stereoselectivities in many cases. In terms of biological activities， representative pyranoindole derivatives have shown promising results in various pharmacological assays. Despite these findings， several challenges remain in the development of pyranoindole-based drug candidates. The natural sources of these compounds are limited， necessitating efficient chemical or biosynthetic approaches. However， existing synthetic routes often suffer from lengthy procedures， poor regio- and stereocontrol， and a limited substrate scope. Moreover， the structural diversity of pyranoindoles has not yet been fully exploited， particularly in terms of their asymmetric synthesis. Most biological studies are still in the preliminary stages of screening. The precise molecular targets， mechanisms of action， and comprehensive structure-activity relationships (SARs) remain largely unclear. To address these issues， future studies should focus on integrating synthetic organic chemistry and biology to develop efficient and sustainable synthetic strategies. Therefore， detailed SAR studies and target identification are urgently required to guide rational drug design. If these challenges are successfully addressed， pyranoindole compounds are expected to become promising candidates for treating various diseases， thereby offering new opportunities for drug discovery and development. This review serves as a valuable reference for the discovery and structural optimization of novel pyranoindole-based lead compounds.
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Basic Information:
DOI：10.13822/j.cnki.hxsj.2026.0106
China Classification Code:O626
Citation Information:
[1]GAN Xu-mei,CHEN Wei-jie,WANG Cui-xia ,et al.Research Progress on Synthesis and Biological Activities of Pyranoindole Compounds[J].Chemical Reagents().DOI:10.13822/j.cnki.hxsj.2026.0106.
Fund Information:
广西自然科学基金项目（2025GXNSFBA069322）; 广西高校中青年教师科研基础能力提升项目（2025KY0385）; 广西中医药大学第三批“岐黄工程“高层次人才团队培育项目（202408）;广西中医药大学大学生科研训练课题项目（2022DXS11）
2026-05-19
2026-05-19
2026-05-19