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Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor
The current study describes synthesis of diindolylmethane (DIM) derivatives based-thiadiazole as a new class of urease inhibitors. Diindolylmethane is natural product alkaloid reported to use in medicinal chemistry extensively. Diindolylmethane-based-thiadiazole analogs (1–18) were synthesized and c...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7224224/ https://www.ncbi.nlm.nih.gov/pubmed/32409737 http://dx.doi.org/10.1038/s41598-020-64729-3 |
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author | Taha, Muhammad Rahim, Fazal Khan, Aftab Ahmad Anouar, El Hassane Ahmed, Naveed Shah, Syed Adnan Ali Ibrahim, Mohamed Zakari, Zainul Amiruddin |
author_facet | Taha, Muhammad Rahim, Fazal Khan, Aftab Ahmad Anouar, El Hassane Ahmed, Naveed Shah, Syed Adnan Ali Ibrahim, Mohamed Zakari, Zainul Amiruddin |
author_sort | Taha, Muhammad |
collection | PubMed |
description | The current study describes synthesis of diindolylmethane (DIM) derivatives based-thiadiazole as a new class of urease inhibitors. Diindolylmethane is natural product alkaloid reported to use in medicinal chemistry extensively. Diindolylmethane-based-thiadiazole analogs (1–18) were synthesized and characterized by various spectroscopic techniques (1)HNMR, (13)C-NMR, EI-MS and evaluated for urease (jack bean urease) inhibitory potential. All compounds showed excellent to moderate inhibitory potential having IC(50) value within the range of 0.50 ± 0.01 to 33.20 ± 1.20 µM compared with the standard thiourea (21.60 ± 0.70 µM). Compound 8 (IC(50) = 0.50 ± 0.01 µM) was the most potent inhibitor amongst all derivatives. Structure-activity relationships have been established for all compounds. The key binding interactions of most active compounds with enzyme were confirmed through molecular docking studies. |
format | Online Article Text |
id | pubmed-7224224 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-72242242020-05-20 Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor Taha, Muhammad Rahim, Fazal Khan, Aftab Ahmad Anouar, El Hassane Ahmed, Naveed Shah, Syed Adnan Ali Ibrahim, Mohamed Zakari, Zainul Amiruddin Sci Rep Article The current study describes synthesis of diindolylmethane (DIM) derivatives based-thiadiazole as a new class of urease inhibitors. Diindolylmethane is natural product alkaloid reported to use in medicinal chemistry extensively. Diindolylmethane-based-thiadiazole analogs (1–18) were synthesized and characterized by various spectroscopic techniques (1)HNMR, (13)C-NMR, EI-MS and evaluated for urease (jack bean urease) inhibitory potential. All compounds showed excellent to moderate inhibitory potential having IC(50) value within the range of 0.50 ± 0.01 to 33.20 ± 1.20 µM compared with the standard thiourea (21.60 ± 0.70 µM). Compound 8 (IC(50) = 0.50 ± 0.01 µM) was the most potent inhibitor amongst all derivatives. Structure-activity relationships have been established for all compounds. The key binding interactions of most active compounds with enzyme were confirmed through molecular docking studies. Nature Publishing Group UK 2020-05-14 /pmc/articles/PMC7224224/ /pubmed/32409737 http://dx.doi.org/10.1038/s41598-020-64729-3 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Taha, Muhammad Rahim, Fazal Khan, Aftab Ahmad Anouar, El Hassane Ahmed, Naveed Shah, Syed Adnan Ali Ibrahim, Mohamed Zakari, Zainul Amiruddin Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor |
title | Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor |
title_full | Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor |
title_fullStr | Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor |
title_full_unstemmed | Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor |
title_short | Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor |
title_sort | synthesis of diindolylmethane (dim) bearing thiadiazole derivatives as a potent urease inhibitor |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7224224/ https://www.ncbi.nlm.nih.gov/pubmed/32409737 http://dx.doi.org/10.1038/s41598-020-64729-3 |
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