Design and Synthesis of 1,3-Diarylpyrazoles and Investigation of Their Cytotoxicity and Antiparasitic Profile

Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound /HIT 8. We previously identified this molecule as a 'hit' during a high-throughput screening campaign for autophagy inducers. A variety of synthetic strategies were utilized to modify the 1,3-diarylpyrazole co...

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Published inInternational journal of molecular sciences Vol. 25; no. 9; p. 4693
Main Authors Bozdag, Murat, Mertens, Freke, Matheeussen, An, Van Pelt, Natascha, Foubert, Kenn, Hermans, Nina, De Meyer, Guido R Y, Augustyns, Koen, Martinet, Wim, Caljon, Guy, Van der Veken, Pieter
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.05.2024
Subjects
1,3-diarylpyrazole
Acids
antiparasitic activity
Antiparasitic Agents - chemical synthesis
Antiparasitic Agents - chemistry
Antiparasitic Agents - pharmacology
Antiprotozoal Agents - chemical synthesis
Antiprotozoal Agents - chemistry
Antiprotozoal Agents - pharmacology
Autophagy
Cells
Chemistry
Crizotinib
Cytotoxicity
Drug Design
Gram-positive bacteria
Humans
Investigations
Kinases
Leishmania infantum - drug effects
Nonsteroidal anti-inflammatory drugs
Permeability
pyrazole
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Stanozolol
Structure-Activity Relationship
Tropical diseases
Trypanosoma brucei rhodesiense - drug effects
Trypanosoma cruzi - drug effects
Belgium
pyrazole
antiparasitic activity
1,3-diarylpyrazole
cytotoxicity
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Abstract Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound /HIT 8. We previously identified this molecule as a 'hit' during a high-throughput screening campaign for autophagy inducers. A variety of synthetic strategies were utilized to modify the 1,3-diarylpyrazole core at its 1-, 3-, and 4-position. Compounds were assessed in vitro to identify their cytotoxicity properties. Of note, several compounds in the series displayed relevant cytotoxicity, which warrants scrutiny while interpreting biological activities that have been reported for structurally related molecules. In addition, antiparasitic activities were recorded against a range of human-infective protozoa, including , , and . The most interesting compounds displayed low micromolar whole-cell potencies against individual or several parasitic species, while lacking cytotoxicity against human cells.
AbstractList Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound 26/HIT 8. We previously identified this molecule as a ‘hit’ during a high-throughput screening campaign for autophagy inducers. A variety of synthetic strategies were utilized to modify the 1,3-diarylpyrazole core at its 1-, 3-, and 4-position. Compounds were assessed in vitro to identify their cytotoxicity properties. Of note, several compounds in the series displayed relevant cytotoxicity, which warrants scrutiny while interpreting biological activities that have been reported for structurally related molecules. In addition, antiparasitic activities were recorded against a range of human-infective protozoa, including Trypanosoma cruzi, T. brucei rhodesiense, and Leishmania infantum. The most interesting compounds displayed low micromolar whole-cell potencies against individual or several parasitic species, while lacking cytotoxicity against human cells.
Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound 26/HIT 8. We previously identified this molecule as a 'hit' during a high-throughput screening campaign for autophagy inducers. A variety of synthetic strategies were utilized to modify the 1,3-diarylpyrazole core at its 1-, 3-, and 4-position. Compounds were assessed in vitro to identify their cytotoxicity properties. Of note, several compounds in the series displayed relevant cytotoxicity, which warrants scrutiny while interpreting biological activities that have been reported for structurally related molecules. In addition, antiparasitic activities were recorded against a range of human-infective protozoa, including Trypanosoma cruzi, T. brucei rhodesiense, and Leishmania infantum. The most interesting compounds displayed low micromolar whole-cell potencies against individual or several parasitic species, while lacking cytotoxicity against human cells.Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound 26/HIT 8. We previously identified this molecule as a 'hit' during a high-throughput screening campaign for autophagy inducers. A variety of synthetic strategies were utilized to modify the 1,3-diarylpyrazole core at its 1-, 3-, and 4-position. Compounds were assessed in vitro to identify their cytotoxicity properties. Of note, several compounds in the series displayed relevant cytotoxicity, which warrants scrutiny while interpreting biological activities that have been reported for structurally related molecules. In addition, antiparasitic activities were recorded against a range of human-infective protozoa, including Trypanosoma cruzi, T. brucei rhodesiense, and Leishmania infantum. The most interesting compounds displayed low micromolar whole-cell potencies against individual or several parasitic species, while lacking cytotoxicity against human cells.
Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound /HIT 8. We previously identified this molecule as a 'hit' during a high-throughput screening campaign for autophagy inducers. A variety of synthetic strategies were utilized to modify the 1,3-diarylpyrazole core at its 1-, 3-, and 4-position. Compounds were assessed in vitro to identify their cytotoxicity properties. Of note, several compounds in the series displayed relevant cytotoxicity, which warrants scrutiny while interpreting biological activities that have been reported for structurally related molecules. In addition, antiparasitic activities were recorded against a range of human-infective protozoa, including , , and . The most interesting compounds displayed low micromolar whole-cell potencies against individual or several parasitic species, while lacking cytotoxicity against human cells.
Audience Academic
Author De Meyer, Guido R Y
Martinet, Wim
Caljon, Guy
Mertens, Freke
Van Pelt, Natascha
Hermans, Nina
Van der Veken, Pieter
Bozdag, Murat
Matheeussen, An
Augustyns, Koen
Foubert, Kenn
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  givenname: Wim
  orcidid: 0000-0003-1967-9343
  surname: Martinet
  fullname: Martinet, Wim
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  givenname: Guy
  orcidid: 0000-0002-4870-3202
  surname: Caljon
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  surname: Van der Veken
  fullname: Van der Veken, Pieter
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Snippet Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound /HIT 8. We previously identified this molecule as a 'hit' during a...
Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound 26/HIT 8. We previously identified this molecule as a ‘hit’ during a...
Herein, we report a series of 1,3-diarylpyrazoles that are analogues of compound 26/HIT 8. We previously identified this molecule as a 'hit' during a...
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StartPage 4693
SubjectTerms 1,3-diarylpyrazole
Acids
antiparasitic activity
Antiparasitic Agents - chemical synthesis
Antiparasitic Agents - chemistry
Antiparasitic Agents - pharmacology
Antiprotozoal Agents - chemical synthesis
Antiprotozoal Agents - chemistry
Antiprotozoal Agents - pharmacology
Autophagy
Cells
Chemistry
Crizotinib
Cytotoxicity
Drug Design
Gram-positive bacteria
Humans
Investigations
Kinases
Leishmania infantum - drug effects
Nonsteroidal anti-inflammatory drugs
Permeability
pyrazole
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Stanozolol
Structure-Activity Relationship
Tropical diseases
Trypanosoma brucei rhodesiense - drug effects
Trypanosoma cruzi - drug effects
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Title Design and Synthesis of 1,3-Diarylpyrazoles and Investigation of Their Cytotoxicity and Antiparasitic Profile
URI https://www.ncbi.nlm.nih.gov/pubmed/38731916
https://www.proquest.com/docview/3053192743
https://www.proquest.com/docview/3053977081
https://doaj.org/article/18dabefed2da4cbd90ffbaf508400672
Volume 25
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