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Article

New Mono- and Diesters with Imidazoquinolinone Ring- Synthesis, Structure Characterization, and Molecular Modeling

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Department Organic Chemistry, Institution Rzeszów University of Technology, Powstańców Warszawy 6, 35-959 Rzeszów, Poland
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Department Chemistry, Institution Tomas Bata University in Zlin, CZ-76272 Zlin, Czech Republic
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Department Biotechnology and Bioinformatic, Institution Rzeszów University of Technology, Powstańców Warszawy 6, 35-959 Rzeszów, Poland
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Research Institute for Organic Syntheses (VUOS), CZ-53354 Pardubice, Czech Republic
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Author to whom correspondence should be addressed.
Molecules 2020, 25(18), 4303; https://doi.org/10.3390/molecules25184303
Received: 27 August 2020 / Revised: 11 September 2020 / Accepted: 17 September 2020 / Published: 19 September 2020
(This article belongs to the Section Molecular Structure)
The objective of the studies was to synthesize and characterize new mono- and diesters with an imidazoquinolin-2-one ring with the use of 2,3-dihydro-2-thioxo-1H-imidazo[4 ,5-c]-quinolin-4(5H)-ones and ethyl bromoacetate. The products were isolated at high yield and characterized by instrumental methods (IR, 1H-, 13C-, and 15N- NMR, MS-ESI, HR-MS, EA). In order to clarify the places of substitution and the structure of the derivatives obtained, molecular modeling of substrates and products was performed. Consideration of the possible tautomeric structures of the substrates confirmed the existence only the most stable keto form. Based on the free energy of monosubstituted ester derivatives, the most stable form were derivatives substituted at sulfur atom of enolic form the used imidazoquinolones. Enolic form referred only to nitrogen atom no 1. The modeling results were consistent with the experimental data. The HOMO electron densities at selected atoms of each substrate has shown that the most reactive atom is sulfur atom. It explained the formation of monoderivatives substituted at sulfur atom. The diester derivatives of the used imidazoquinolones had second substituent at nitrogen atom no. 3. The new diesters can be used as raw material for synthesis of thermally stable polymers, and they can also have biological activity. View Full-Text
Keywords: ammonium thiocyanate; debenzylation; 3-hydroxyquinolinediones; thioxoimidazoquinolinone ring; molecular modeling ammonium thiocyanate; debenzylation; 3-hydroxyquinolinediones; thioxoimidazoquinolinone ring; molecular modeling
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MDPI and ACS Style

Zarzyka, I.; Klásek, A.; Hęclik, K.; Lyčka, A.; Bartošík, R.; Dobrowolski, L. New Mono- and Diesters with Imidazoquinolinone Ring- Synthesis, Structure Characterization, and Molecular Modeling. Molecules 2020, 25, 4303. https://doi.org/10.3390/molecules25184303

AMA Style

Zarzyka I, Klásek A, Hęclik K, Lyčka A, Bartošík R, Dobrowolski L. New Mono- and Diesters with Imidazoquinolinone Ring- Synthesis, Structure Characterization, and Molecular Modeling. Molecules. 2020; 25(18):4303. https://doi.org/10.3390/molecules25184303

Chicago/Turabian Style

Zarzyka, Iwona, Antonin Klásek, Karol Hęclik, Antonin Lyčka, Radek Bartošík, and Lucjan Dobrowolski. 2020. "New Mono- and Diesters with Imidazoquinolinone Ring- Synthesis, Structure Characterization, and Molecular Modeling" Molecules 25, no. 18: 4303. https://doi.org/10.3390/molecules25184303

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