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Synthesis 2018; 50(23): 4525-4538
DOI: 10.1055/s-0037-1610288
review
© Georg Thieme Verlag Stuttgart · New York

Utilization of 1H-Indole-3-carboxaldehyde as a Precursor for the Synthesis of Bioactive Indole Alkaloids

Eslam R. El-Sawy
a   Université de Lorraine, Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), 1 Boulevard Arago, 57070, France   Email: gilbert.kirsch@univ-lorraine.fr
b   Chemistry of Natural Compounds Department, National Research Centre, El-Behoos St. 33, Dokki-Cairo 12622, Egypt
,
Ahmed B. Abdelwahab
a   Université de Lorraine, Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), 1 Boulevard Arago, 57070, France   Email: gilbert.kirsch@univ-lorraine.fr
b   Chemistry of Natural Compounds Department, National Research Centre, El-Behoos St. 33, Dokki-Cairo 12622, Egypt
,
Gilbert Kirsch*
a   Université de Lorraine, Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), 1 Boulevard Arago, 57070, France   Email: gilbert.kirsch@univ-lorraine.fr
› Author AffiliationsThis work was supported by the French and Egyptian governments through a co-financed fellowship granted by the French Embassy in Egypt (Institut Français d'Egypte) and the Science and Technology Development Fund (STDF). Additionally, Plant Advanced Technologies (PAT) Company, Nancy, Franceis gratefully acknowledged for funding the postdoc program of A B. Abdelwahab.
Further Information

Publication History

Received: 09 July 2018

Accepted after revision: 23 August 2018

Publication Date:
15 October 2018 (online)

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Abstract

Indole alkaloids constitute a large class of natural products and their diverse and complex structures have been attributed to potent biological activities such as anticancer, anti-inflammatory, antimicrobial, antimalarial, antiplasmodial and protein kinase inhibition. The isolation of bioactive compounds from natural sources is difficult, costly and an extremely time-consuming process, therefore synthetic pathways are more convenient than natural separation to deliver such compounds in considerable amounts. In this respect, this review provides comprehensive information on the structures and the synthesis of bioactive indole alkaloids utilizing 1H-indole-3-carboxaldehyde and its derivatives as starting compounds.

1 Overview

2 Phytoalexins

2.1 Brassinin, Cyclobrassinin and Brassitin

2.2 1-Methoxybrassinin, 1-Methoxyspirobrassinol and 1-Methoxyspirobrassinin

2.3 4-Methoxybrassinin and 4-Methoxycyclobrassinin

2.4 Cyclobrassinone

2.5 Brassilexin

2.6 (S)-(–)-Spirobrassinin

2.7 Camalexin

3 Bis(indole) Alkaloids: Rhopaladines A–D

4 Coscinamides A and B

5 α-Cyclopiazonic Acid

6 Dipodazine

7 Isocryptolepine

8 Apparicine

9 Carbazole Alkaloids: Mukonine and Clausine E

10 Indolmycin

11 Conclusion

Key words

indoles - 1H-indole-3-carboxaldehyde - synthesis - alkaloids - bioactivity
 

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