N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

Valentin Wydra; Stefan Gerstenecker; Dieter Schollmeyer; Stanislav Andreev; Teodor Dimitrov; Ricardo Augusto Massarico Serafim; Stefan Laufer; Matthias Gehringer

doi:10.3390/M1181

N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

Valentin Wydra
, Stefan Gerstenecker
, Dieter Schollmeyer
, Stanislav Andreev
, Teodor Dimitrov
, Ricardo Augusto Massarico Serafim
, Stefan Laufer
, Matthias Gehringer^*

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

5 Citations (Scopus)

Abstract

Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald-Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (H-1, C-13, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6K beta /S6K2).

Original language	English
Article number	M1181
Number of pages	6
Journal	Molbank
Volume	2021
Issue number	1
DOIs	https://doi.org/10.3390/M1181
Publication status	Published - Mar 2021
Externally published	Yes

Keywords

3-nitropyridines
Buchwald-Hartwig arylamination
Covalent inhibitors
Nucleophilic aromatic substitution
Protein kinase inhibitors

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title = "N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine",

abstract = "Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald-Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (H-1, C-13, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6K beta /S6K2).",

keywords = "3-nitropyridines, Buchwald-Hartwig arylamination, Covalent inhibitors, Nucleophilic aromatic substitution, Protein kinase inhibitors",

author = "Valentin Wydra and Stefan Gerstenecker and Dieter Schollmeyer and Stanislav Andreev and Teodor Dimitrov and \{Massarico Serafim\}, \{Ricardo Augusto\} and Stefan Laufer and Matthias Gehringer",

year = "2021",

month = mar,

doi = "10.3390/M1181",

language = "English",

volume = "2021",

journal = "Molbank",

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T1 - N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

AU - Wydra, Valentin

AU - Gerstenecker, Stefan

AU - Schollmeyer, Dieter

AU - Andreev, Stanislav

AU - Dimitrov, Teodor

AU - Massarico Serafim, Ricardo Augusto

AU - Laufer, Stefan

AU - Gehringer, Matthias

PY - 2021/3

Y1 - 2021/3

N2 - Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald-Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (H-1, C-13, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6K beta /S6K2).

AB - Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald-Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (H-1, C-13, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6K beta /S6K2).

KW - 3-nitropyridines

KW - Buchwald-Hartwig arylamination

KW - Covalent inhibitors

KW - Nucleophilic aromatic substitution

KW - Protein kinase inhibitors

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N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

Abstract

Keywords

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