Three overlooked chemical approaches toward 3-naphthalimide amonafide N-derivatives

Tamara Brider; Boris Redko; Flavio Grynszpan; Gary Gellerman

doi:10.1016/j.tetlet.2014.10.059

Three overlooked chemical approaches toward 3-naphthalimide amonafide N-derivatives

Tamara Brider
, Boris Redko
, Flavio Grynszpan
, Gary Gellerman

Ariel University

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Three efficient strategies for derivatization of the anticancer drug candidate amonafide (Quinamed, originally AS1413) are described. Unprecedented reductive amination of aryl aldehydes, S_NAr, and addition-elimination reactions, while using readily available starting materials, give quick entry to potential libraries of novel 3-aryl, 3-benzyl N-derivatives of amonafide. The selective anticancer activity of this important DNA intercalation agent is expected to be enhanced by expanding the diversity of amonafide N-derivatives. The synthetic routes reported in this work are general and readily applicable.

Original language	English
Pages (from-to)	6675-6679
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2014.10.059
State	Published - 3 Dec 2014
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

Keywords

Addition-elimination reaction
Amonafide
Anticancer
DNA intercalator
Hybrid
SAr

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10.1016/j.tetlet.2014.10.059

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AU - Redko, Boris

AU - Grynszpan, Flavio

AU - Gellerman, Gary

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KW - Addition-elimination reaction

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KW - Anticancer

KW - DNA intercalator

KW - Hybrid

KW - SAr

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JO - Tetrahedron Letters

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Three overlooked chemical approaches toward 3-naphthalimide amonafide N-derivatives

Abstract

Bibliographical note

Keywords

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