NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives

J 2008

NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives

TSIKOURIS, Orestis, Tomáš BARTL, Jaromír TOUŠEK, Nikolaos LOUGIAKIS, Tony TITE et. al.

Basic information

Original name

NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives

Name in Czech

NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives

Authors

TSIKOURIS, Orestis (300 Greece), Tomáš BARTL (203 Czech Republic), Jaromír TOUŠEK (203 Czech Republic, belonging to the institution), Nikolaos LOUGIAKIS (300 Greece), Tony TITE (300 Greece), Panagiotis MARAKOS (300 Greece), Nicole POULI (300 Greece), Emmanuel MIKROS (300 Greece) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution)

Edition

Magnetic Resonance in Chemistry, John Wiley & Sons, 2008, 0749-1581

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

DOI: 10.1002/mrc.2226

Impact factor

Impact factor: 1.443

RIV identification code

RIV/00216224:14310/08:00025874

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/mrc.2226

UT WoS

000257052400005

Keywords in English

NMR; 1H; 13C; 15N; tautomerism; spin-spin coupling constant; purine; pyrazolo[3.4-c]pyridine; quantum-chemical calculation

Abstract

ORIG CZ

V originále

Substituted pyrazolopyridines are potent inhibitors of phosphodiesterases and cyclin-dependent kinases. In this study, NMR was used to investigate the potential N1-H and N2-H tautomerism of 5-substituted pyrazolo[3,4-c]pyridine derivatives. Six compounds were fully characterized by using 1H, 13C, and 15N chemical shifts and indirect 1H-13C and 1H-15N coupling constants. The 1H NMR spectra were measured over a broad range of temperatures. All of the compounds were shown to exist predominantly in the N1-H tautomeric form. Complementary quantum-chemical calculations of the chemical shieldings and indirect spin-spin couplings support the structural conclusions drawn.

In Czech

Tautomerní NMR studie 5-substituovaných derivátů pyrazolo[3,4-c]pyridinu.

Links

LC06030, research and development project

Name: Biomolekulární centrum

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre

MSM0021622413, plan (intention)

Name: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment

Files attached

MRC08_46_643.pdf

Request the author's version of the file

Citovat

TSIKOURIS, Orestis, Tomáš BARTL, Jaromír TOUŠEK, Nikolaos LOUGIAKIS, Tony TITE, Panagiotis MARAKOS, Nicole POULI, Emmanuel MIKROS and Radek MAREK. NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives. Magnetic Resonance in Chemistry. John Wiley & Sons, 2008, vol. 46, No 7, p. 643-649. ISSN 0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2226.

@article{763746,
   author = {Tsikouris, Orestis and Bartl, Tomáš and Toušek, Jaromír and Lougiakis, Nikolaos and Tite, Tony and Marakos, Panagiotis and Pouli, Nicole and Mikros, Emmanuel and Marek, Radek},
   article_number = {7},
   doi = {http://dx.doi.org/10.1002/mrc.2226},
   keywords = {NMR; 1H; 13C; 15N; tautomerism; spin-spin coupling constant; purine; pyrazolo[3.4-c]pyridine; quantum-chemical calculation},
   language = {eng},
   issn = {0749-1581},
   journal = {Magnetic Resonance in Chemistry},
   title = {NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives},
   url = {http://dx.doi.org/10.1002/mrc.2226},
   volume = {46},
   year = {2008}
}

TY  - JOUR
ID  - 763746
AU  - Tsikouris, Orestis - Bartl, Tomáš - Toušek, Jaromír - Lougiakis, Nikolaos - Tite, Tony - Marakos, Panagiotis - Pouli, Nicole - Mikros, Emmanuel - Marek, Radek
PY  - 2008
TI  - NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives
JF  - Magnetic Resonance in Chemistry
VL  - 46
IS  - 7
SP  - 643-649
EP  - 643-649
PB  - John Wiley & Sons
SN  - 07491581
KW  - NMR
KW  - 1H
KW  - 13C
KW  - 15N
KW  - tautomerism
KW  - spin-spin coupling constant
KW  - purine
KW  - pyrazolo[3.4-c]pyridine
KW  - quantum-chemical calculation
UR  - http://dx.doi.org/10.1002/mrc.2226
L2  - http://dx.doi.org/10.1002/mrc.2226
N2  - Substituted pyrazolopyridines are potent inhibitors of phosphodiesterases and cyclin-dependent kinases. In this study, NMR was used to investigate the potential N1-H and N2-H tautomerism of 5-substituted pyrazolo[3,4-c]pyridine derivatives. Six compounds were fully characterized by using 1H, 13C, and 15N chemical shifts and indirect 1H-13C and 1H-15N coupling constants. The 1H NMR spectra were measured over a broad range of temperatures. All of the compounds were shown to exist predominantly in the N1-H tautomeric form. Complementary quantum-chemical calculations of the chemical shieldings and indirect spin-spin couplings support the structural conclusions drawn.
ER  -

TSIKOURIS, Orestis, Tomáš BARTL, Jaromír TOUŠEK, Nikolaos LOUGIAKIS, Tony TITE, Panagiotis MARAKOS, Nicole POULI, Emmanuel MIKROS and Radek MAREK. NMR study of 5-substituted pyrazolo[3,4-c]pyridine derivatives. \textit{Magnetic Resonance in Chemistry}. John Wiley \&{} Sons, 2008, vol.~46, No~7, p.~643-649. ISSN~0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2226.

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