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Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.

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2019
Biological_Potential_of_acc_2019.pdf (1.271Mb)
Authors
Sović, Irena
Cindrić, Maja
Perin, Nataša
Boček, Ida
Novaković, Irena
Damjanović, Ana
Stanojković, Tatjana
Zlatović, Mario
Hranjec, Marijana
Bertoša, Branimir
Article (Accepted Version)
,
American Chemical Society (ACS)
Metadata
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Abstract
This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compound...s are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.

Source:
Chemical Research in Toxicology, 2019, 32, 9, 1880-1892
Publisher:
  • American Chemical Society (ACS)
Funding / projects:
  • Croatian Science Foundation under the project 4379 entitled Exploring the antioxidative potential of benzazole scaffold in the design of novel antitumor agents.
Note:
  • This is the peer-reviewed version of the following article: Sović, I.; Cindrić, M.; Perin, N.; Boček, I.; Novaković, I. T.; Damjanović, A.; Stanojković, T.; Zlatović, M.; Hranjec, M.; Bertoša, B. Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity. Chemical Research in Toxicology 2019, 32 (9), 1880. https://doi.org/10.1021/acs.chemrestox.9b00256
  • The published version: http://cer.ihtm.bg.ac.rs/handle/123456789/3416

DOI: 10.1021/acs.chemrestox.9b00256

ISSN: 0893-228X

WoS: 000486565700015

Scopus: 2-s2.0-85071730814
[ Google Scholar ]
5
5
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3464
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Sović, Irena
AU  - Cindrić, Maja
AU  - Perin, Nataša
AU  - Boček, Ida
AU  - Novaković, Irena
AU  - Damjanović, Ana
AU  - Stanojković, Tatjana
AU  - Zlatović, Mario
AU  - Hranjec, Marijana
AU  - Bertoša, Branimir
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3464
AB  - This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compounds are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.
PB  - American Chemical Society (ACS)
T2  - Chemical Research in Toxicology
T1  - Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.
VL  - 32
IS  - 9
SP  - 1880
EP  - 1892
DO  - 10.1021/acs.chemrestox.9b00256
ER  - 
@article{
author = "Sović, Irena and Cindrić, Maja and Perin, Nataša and Boček, Ida and Novaković, Irena and Damjanović, Ana and Stanojković, Tatjana and Zlatović, Mario and Hranjec, Marijana and Bertoša, Branimir",
year = "2019",
abstract = "This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compounds are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.",
publisher = "American Chemical Society (ACS)",
journal = "Chemical Research in Toxicology",
title = "Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.",
volume = "32",
number = "9",
pages = "1880-1892",
doi = "10.1021/acs.chemrestox.9b00256"
}
Sović, I., Cindrić, M., Perin, N., Boček, I., Novaković, I., Damjanović, A., Stanojković, T., Zlatović, M., Hranjec, M.,& Bertoša, B.. (2019). Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.. in Chemical Research in Toxicology
American Chemical Society (ACS)., 32(9), 1880-1892.
https://doi.org/10.1021/acs.chemrestox.9b00256
Sović I, Cindrić M, Perin N, Boček I, Novaković I, Damjanović A, Stanojković T, Zlatović M, Hranjec M, Bertoša B. Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.. in Chemical Research in Toxicology. 2019;32(9):1880-1892.
doi:10.1021/acs.chemrestox.9b00256 .
Sović, Irena, Cindrić, Maja, Perin, Nataša, Boček, Ida, Novaković, Irena, Damjanović, Ana, Stanojković, Tatjana, Zlatović, Mario, Hranjec, Marijana, Bertoša, Branimir, "Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity." in Chemical Research in Toxicology, 32, no. 9 (2019):1880-1892,
https://doi.org/10.1021/acs.chemrestox.9b00256 . .

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