One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors
Publication type: Journal Article
Publication date: 2019-11-26
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31769674
Organic Chemistry
Abstract
A new, efficient, and versatile one-pot cascade reaction of diverse Gewald's aminothiophenes, 2-hydroxy-4-oxobut-2-enoic acid, and derivatives of cyanoacetic acid catalyzed by Et3N is presented. It enables direct synthesis of diverse 1-(2-oxoethylidene)-2-oxothieno[3,2-e]pyrrolo[1,2-a]pyrimidine in good to excellent yields. The reaction exhibits a broad substrate scope and also presents an opportunity for further modification of the structure. The method offers a convenient practical alternative to the known procedures. The synthesized thieno[3,2-e]pyrrolo[1,2-a]pyrimidine scaffold is an important structural motif of new poly(ADP-ribose) polymerase (PARP) inhibitors, playing a useful role in multiple pharmacological applications.
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Total citations:
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Citations from 2024:
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(12.24%)
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GOST
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Shipilovskikh S. A., Rubtsov A. E. One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors // Journal of Organic Chemistry. 2019. Vol. 84. No. 24. pp. 15788-15796.
GOST all authors (up to 50)
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Shipilovskikh S. A., Rubtsov A. E. One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors // Journal of Organic Chemistry. 2019. Vol. 84. No. 24. pp. 15788-15796.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b00711
UR - https://doi.org/10.1021/acs.joc.9b00711
TI - One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors
T2 - Journal of Organic Chemistry
AU - Shipilovskikh, Sergei A
AU - Rubtsov, Aleksandr E
PY - 2019
DA - 2019/11/26
PB - American Chemical Society (ACS)
SP - 15788-15796
IS - 24
VL - 84
PMID - 31769674
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Shipilovskikh,
author = {Sergei A Shipilovskikh and Aleksandr E Rubtsov},
title = {One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.9b00711},
number = {24},
pages = {15788--15796},
doi = {10.1021/acs.joc.9b00711}
}
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MLA
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Shipilovskikh, Sergei A., et al. “One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors.” Journal of Organic Chemistry, vol. 84, no. 24, Nov. 2019, pp. 15788-15796. https://doi.org/10.1021/acs.joc.9b00711.