1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity

Jean Guillon,Noël Pinaud,Solène Savrimoutou,Sandra Rubio,Vanessa Desplat,Mathieu Marchivie,Stéphane Moreau

doi:10.3390/m1113

Abstract

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells).

Highlights

Heterocyclic derivatives have attracted a lot of attention, due to their wide spread biological activities
We report on the synthesis and structural identification of the
The reaction of 3 with triphosgene in refluxing toluene gave the lactam 4, which was subsequently chlorodehydroxylated with phosphorous oxychloride (POCl3 ), leading to the 4-chloroquinoxaline

Summary

Introduction

Heterocyclic derivatives have attracted a lot of attention, due to their wide spread biological activities. We recently published a few series of new pyrrolo[1,2-a]quinoxaline derivatives endowed with promising biological activity towards the human leukemia cells [13,14,15,16]. These antileukemial pyrroloquinoxaline derivatives were previously reported as new structural analogues of derivative A6730 (Figure 1), a reference Protein kinase B

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Conclusion