Efficient synthesis of some new antiproliferative N-fused indoles and isoquinolines via 1,3-dipolar cycloaddition reaction in an ionic liquid

Tushar R Sutariya,Rajni Kant,Vivek K Gupta,Balvantsingh M Labana,José M Padrón,Gabriela B Plata,Narsidas J Parmar

doi:10.1039/c4nj02308k

Tushar R Sutariya, Rajni Kant + Show 5 more

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https://doi.org/10.1039/c4nj02308k

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Abstract

Triethylammonium acetate (TEAA) as a new, recyclable and environmentally friendly reaction medium for the intramolecular[3+2] cycloaddition reaction.

Highlights

The heterocycles with a N-fused indole/isoquinoline-heterocyclic framework as one of their integral structural units constitute an important class of bioprofiles, and have attracted the interest of many in the research fields of medicines and pharmaceuticals
As part of our research program, we have reported the synthesis of many pyran-heterocycles.20h including aminobenzopyrans20h,i via 1,3 dipolar cycloaddition
Teterahydroisoquinolines 6 were used as received from commercial sources

Summary

Introduction

The heterocycles with a N-fused indole/isoquinoline-heterocyclic framework as one of their integral structural units constitute an important class of bioprofiles, and have attracted the interest of many in the research fields of medicines and pharmaceuticals. Containing the pyrrolo-indole nucleus, terpenoidal alkaloids and mitomycins exhibited antitumor activity (Fig. 1A). With pyrrolo[1,2-a]indole as a specific fusion, cyclopropamitosenes revealed cytotoxicity through bacterial cell division and DNA alkylation. Likewise, antimalarial Flinderole B,5 bioactive Isatisine A (Fig. 1B) and hallucinogenic Yuremamine (Fig. 1C), which are potential candidates of this class have attracted the interest of many chemists and biochemists.7Pyrrolo-isoquinoline alkaloids, on the other hand, showed promising results for depression in animals, with the pyrroloisoquinoline nucleus. A tricyclic hydropyrrolo [2,1-a] isoquinoline is a key fused-ring system with (2)-trolline structure, which (+)-crispine A (Fig. 1D) incorporates an analogous heterocyclic framework and has potential anti-proliferative activity against SKOV3, KB, and HeLa human cancer lines.. The heterocycles with a N-fused indole/isoquinoline-heterocyclic framework as one of their integral structural units constitute an important class of bioprofiles, and have attracted the interest of many in the research fields of medicines and pharmaceuticals.. Containing the pyrrolo-indole nucleus, terpenoidal alkaloids and mitomycins exhibited antitumor activity (Fig. 1A).. Antimalarial Flinderole B,5 bioactive Isatisine A (Fig. 1B) and hallucinogenic Yuremamine (Fig. 1C), which are potential candidates of this class have attracted the interest of many chemists and biochemists.. Pyrrolo-isoquinoline alkaloids, on the other hand, showed promising results for depression in animals, with the pyrroloisoquinoline nucleus.. A tricyclic hydropyrrolo [2,1-a] isoquinoline is a key fused-ring system with (2)-trolline structure, which (+)-crispine A (Fig. 1D) incorporates an analogous heterocyclic framework and has potential anti-proliferative activity against SKOV3, KB, and HeLa human cancer lines.

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Conclusion