Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase
In this study, a stepwise reaction afforded thiazolidinone-based benzothiazole derivatives <b>1</b>–<b>15</b>, and the synthesized derivatives were then screened for biological significance and found to be the leading candidates against α-amylase and α-glucosidase enzymes. Al...
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| Format: | Article |
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MDPI AG
2022-09-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/15/10/1164 |
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| author | Shoaib Khan Shahid Iqbal Marwa Khan Wajid Rehman Mazloom Shah Rafaqat Hussain Liaqat Rasheed Yousaf Khan Ayed A. Dera Rami Adel Pashameah Eman Alzahrani Abd-ElAziem Farouk |
| author_facet | Shoaib Khan Shahid Iqbal Marwa Khan Wajid Rehman Mazloom Shah Rafaqat Hussain Liaqat Rasheed Yousaf Khan Ayed A. Dera Rami Adel Pashameah Eman Alzahrani Abd-ElAziem Farouk |
| author_sort | Shoaib Khan |
| collection | DOAJ |
| description | In this study, a stepwise reaction afforded thiazolidinone-based benzothiazole derivatives <b>1</b>–<b>15</b>, and the synthesized derivatives were then screened for biological significance and found to be the leading candidates against α-amylase and α-glucosidase enzymes. Almost all derivatives showed excellent to good activity ranging against α-amylase, IC50 = 2.10 ± 0.70 to 37.50 ± 0.70 μM, and α-glucosidase, IC50 = 3.20 ± 0.05 to 39.40 ± 0.80 μM. Some analogues such as <b>4</b> (2.40 ± 0.70 and 3.50 ± 0.70 μM), <b>5</b> (2.30 ± 0.05 and 4.80 ± 0.10 μM), and <b>6</b> (2.10 ± 0.70 and 3.20 ± 0.70 μM) were found with folds better activity than that of the standard drug acarbose (9.10 ± 0.10 and 10.70 ± 0.10 μM), respectively. Moreover, the structure–activity relationship (SAR) has been established for all compounds. A molecular docking study has been carried out to explore the binding interactions against α-amylase and α-glucosidase enzymes. |
| first_indexed | 2024-03-09T19:37:37Z |
| format | Article |
| id | doaj.art-78f6e5085b48465a85e293eb392d90c8 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-09T19:37:37Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-78f6e5085b48465a85e293eb392d90c82023-11-24T01:50:10ZengMDPI AGPharmaceuticals1424-82472022-09-011510116410.3390/ph15101164Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-GlucosidaseShoaib Khan0Shahid Iqbal1Marwa Khan2Wajid Rehman3Mazloom Shah4Rafaqat Hussain5Liaqat Rasheed6Yousaf Khan7Ayed A. Dera8Rami Adel Pashameah9Eman Alzahrani10Abd-ElAziem Farouk11Department of Chemistry, Hazara University, Mansehra 21120, PakistanDepartment of Chemistry, School of Natural Sciences (SNS), National University of Science and Technology (NUST), H-12, Islamabad 46000, PakistanDepartment of Chemistry, Hazara University, Mansehra 21120, PakistanDepartment of Chemistry, Hazara University, Mansehra 21120, PakistanDepartment of Chemistry, Abbottabad University of Science and Technology (AUST), Abbottabad 22500, PakistanDepartment of Chemistry, Hazara University, Mansehra 21120, PakistanDepartment of Chemistry, Hazara University, Mansehra 21120, PakistanDepartment of Chemistry, COMSATS University Islamabad Campus, Islamabad 45550, PakistanDepartment of Clinical Laboratory Sciences, College of Applied Medical Sciences, King Khalid University, Abha 61421, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi ArabiaDepartment of Chemistry, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi ArabiaDepartment of Biotechnology, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi ArabiaIn this study, a stepwise reaction afforded thiazolidinone-based benzothiazole derivatives <b>1</b>–<b>15</b>, and the synthesized derivatives were then screened for biological significance and found to be the leading candidates against α-amylase and α-glucosidase enzymes. Almost all derivatives showed excellent to good activity ranging against α-amylase, IC50 = 2.10 ± 0.70 to 37.50 ± 0.70 μM, and α-glucosidase, IC50 = 3.20 ± 0.05 to 39.40 ± 0.80 μM. Some analogues such as <b>4</b> (2.40 ± 0.70 and 3.50 ± 0.70 μM), <b>5</b> (2.30 ± 0.05 and 4.80 ± 0.10 μM), and <b>6</b> (2.10 ± 0.70 and 3.20 ± 0.70 μM) were found with folds better activity than that of the standard drug acarbose (9.10 ± 0.10 and 10.70 ± 0.10 μM), respectively. Moreover, the structure–activity relationship (SAR) has been established for all compounds. A molecular docking study has been carried out to explore the binding interactions against α-amylase and α-glucosidase enzymes.https://www.mdpi.com/1424-8247/15/10/1164synthesisα-amylase and α-glucosidase enzymesthiazolidinonebenzothiazoleSARmolecular docking |
| spellingShingle | Shoaib Khan Shahid Iqbal Marwa Khan Wajid Rehman Mazloom Shah Rafaqat Hussain Liaqat Rasheed Yousaf Khan Ayed A. Dera Rami Adel Pashameah Eman Alzahrani Abd-ElAziem Farouk Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase Pharmaceuticals synthesis α-amylase and α-glucosidase enzymes thiazolidinone benzothiazole SAR molecular docking |
| title | Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase |
| title_full | Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase |
| title_fullStr | Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase |
| title_full_unstemmed | Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase |
| title_short | Design, Synthesis, In Silico Testing, and In Vitro Evaluation of Thiazolidinone-Based Benzothiazole Derivatives as Inhibitors of α-Amylase and α-Glucosidase |
| title_sort | design synthesis in silico testing and in vitro evaluation of thiazolidinone based benzothiazole derivatives as inhibitors of α amylase and α glucosidase |
| topic | synthesis α-amylase and α-glucosidase enzymes thiazolidinone benzothiazole SAR molecular docking |
| url | https://www.mdpi.com/1424-8247/15/10/1164 |
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