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Derivatives of a PARP Inhibitor TIQ-A through the Synthesis of 8-Alkoxythieno[2,3-c]isoquinolin-5(4H)-ones
- Source :
- ACS Omega, Maksimainen, M M, Nurmesjärvi, A, Terho, R A, Threadgill, M D, Lehtiö, L & Heiskanen, J P 2020, ' Derivatives of a PARP Inhibitor TIQ-A through the Synthesis of 8-Alkoxythieno[2,3-c]isoquinolin-5(4 H)-ones ', ACS Omega, vol. 5, no. 22, pp. 13447-13453 . https://doi.org/10.1021/acsomega.0c01879, ACS Omega, Vol 5, Iss 22, Pp 13447-13453 (2020), Maksimainen, M, Nurmesjärvi, A, Terho, R, Threadgill, M, Lehtiö, L & Heiskanen, J 2020, ' Derivatives of a PARP inhibitor TIQ-A through synthesis of 8-alkoxythieno[2,3-c]isoquinolin-5(4H)-ones ', ACS OMEGA . https://doi.org/10.1021/acsomega.0c01879
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
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.
- Subjects :
- chemistry.chemical_classification
biology
010405 organic chemistry
Chemistry
Stereochemistry
General Chemical Engineering
Poly ADP ribose polymerase
General Chemistry
Limiting
010402 general chemistry
01 natural sciences
Article
0104 chemical sciences
PARP1
Enzyme
PARP inhibitor
biology.protein
Selectivity
QD1-999
Polymerase
Subjects
Details
- ISSN :
- 24701343
- Volume :
- 5
- Database :
- OpenAIRE
- Journal :
- ACS Omega
- Accession number :
- edsair.doi.dedup.....28f086bd03668080f6385211645b9ecc