Derivatives of a PARP Inhibitor TIQ-A through the Synthesis of 8-Alkoxythieno[2,3- c]isoquinolin-5(4 H)-ones

Mirko M. Maksimainen, Antti Nurmesjärvi, Reima A. Terho, Michael D. Threadgill, Lari Lehtiö, Juha P. Heiskanen (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Thieno[2,3-c]isoquinolin-5(4H)-one is known for its potential as an anti-ischemic agent through the inhibition of poly(ADP-ribose) polymerase 1 (PARP1). However, the compound also inhibits many other enzymes of the PARP family, potentially limiting its usability. The broad inhibition profile, on the other hand, indicates that this molecule backbone could be potentially used as a scaffold for the development of specific inhibitors for certain PARP enzymes. These efforts call for novel synthetic strategies for substituted thieno[2,3-c]isoquinolin-5(4H)-one that could provide the needed selectivity. In this article, an efficient synthetic strategy for 8-alkoxythieno[2,3-c]isoquinolin-5(4H)-ones through eight steps is presented and other tested synthetic pathways are discussed in detail. Synthesis of 7-methoxythieno[2,3-c]isoquinolin-5(4H)-one is also demonstrated to show that the strategy can be applied widely in the syntheses of substituted alkoxythieno[2,3-c]isoquinolin-5(4H)-ones.

Original languageEnglish
Pages (from-to)13447-13453
Number of pages7
JournalACS Omega
Volume5
Issue number22
DOIs
Publication statusPublished - 9 Jun 2020
MoE publication typeA1 Journal article-refereed

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