Synthesis 2018; 50(07): 1417-1429
DOI: 10.1055/s-0036-1591947
short review
© Georg Thieme Verlag Stuttgart · New York

Isolation, Synthesis, and Biological Activity of Quindoline, a Valuable­ Indoloquinoline Natural Product and Useful Key Intermediate­

María V. Méndez
Instituto de Química Rosario (IQUIR, CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Suipacha 531 (S2002LRK) Rosario, Argentina   Email: kaufman@iquir-conicet.gov.ar
,
Andrea B. J. Bracca
Instituto de Química Rosario (IQUIR, CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Suipacha 531 (S2002LRK) Rosario, Argentina   Email: kaufman@iquir-conicet.gov.ar
,
Teodoro S. Kaufman*
Instituto de Química Rosario (IQUIR, CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Suipacha 531 (S2002LRK) Rosario, Argentina   Email: kaufman@iquir-conicet.gov.ar
› Author Affiliations
CONICET (PIP 2012-0471; PUE IQUIR 2016) and ANPCyT (PICT 2014-0445)
Further Information

Publication History

Received: 22 December 2017

Accepted after revision: 01 February 2018

Publication Date:
26 February 2018 (online)


Abstract

Quindoline is one of the simplest naturally occurring monomeric indoloquinoline alkaloids. Chemists exhibited interest in this compound before it was isolated from a natural source. The different approaches toward the total synthesis of the natural product and its performance in various biological tests are discussed. Aspects related to the isolation of quindoline from different ethnomedicinally relevant plants around the world are also reviewed.

1 Introduction

2 Isolation and Biogenetic Considerations

3 Total Syntheses of Quindoline

3.1 Early Synthetic Studies

3.2 Syntheses from Benzenoids

3.3 Syntheses from Indoles

3.4 Syntheses from Quinolines

4 Biological Activity Studies

5 Conclusions

 
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