Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor
A series of twenty indole hydrazone analogs (1–21) were synthesized, characterized by different spectroscopic techniques such as 1H NMR and EI-MS, and screened for α-amylase inhibitory activity. All analogs showed a variable degree of α-amylase inhibition with IC50 values ranging between 1.66 and 2....
| Published in: | Bioorganic Chemistry |
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| Language: | English |
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Academic Press Inc.
2017
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| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85021060841&doi=10.1016%2fj.bioorg.2017.06.007&partnerID=40&md5=d9e7c98d5a0decd20b6a24143a22fabd |
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2-s2.0-85021060841 Imran S.; Taha M.; Selvaraj M.; Ismail N.H.; Chigurupati S.; Mohammad J.I. Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor 2017 Bioorganic Chemistry 73 10.1016/j.bioorg.2017.06.007 https://www.scopus.com/inward/record.uri?eid=2-s2.0-85021060841&doi=10.1016%2fj.bioorg.2017.06.007&partnerID=40&md5=d9e7c98d5a0decd20b6a24143a22fabd A series of twenty indole hydrazone analogs (1–21) were synthesized, characterized by different spectroscopic techniques such as 1H NMR and EI-MS, and screened for α-amylase inhibitory activity. All analogs showed a variable degree of α-amylase inhibition with IC50 values ranging between 1.66 and 2.65 μM. Nine compounds that are 1 (2.23 ± 0.01 μM), 8 (2.44 ± 0.12 μM), 10 (1.92 ± 0.12 μM), 12 (2.49 ± 0.17 μM), 13 (1.66 ± 0.09 μM), 17 (2.25 ± 0.1 μM), 18 (1.87 ± 0.25 μM), 20 (1.83 ± 0.63 μM), and 19 (1.97 ± 0.02 μM) showed potent α-amylase inhibition when compared with the standard acarbose (1.05 ± 0.29 μM). Other analogs showed good to moderate α-amylase inhibition. The structure activity relationship is mainly focusing on difference of substituents on phenyl part. Molecular docking studies were carried out to understand the binding interaction of the most active compounds. © 2017 Elsevier Inc. Academic Press Inc. 452068 English Article |
| author |
Imran S.; Taha M.; Selvaraj M.; Ismail N.H.; Chigurupati S.; Mohammad J.I. |
| spellingShingle |
Imran S.; Taha M.; Selvaraj M.; Ismail N.H.; Chigurupati S.; Mohammad J.I. Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| author_facet |
Imran S.; Taha M.; Selvaraj M.; Ismail N.H.; Chigurupati S.; Mohammad J.I. |
| author_sort |
Imran S.; Taha M.; Selvaraj M.; Ismail N.H.; Chigurupati S.; Mohammad J.I. |
| title |
Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| title_short |
Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| title_full |
Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| title_fullStr |
Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| title_full_unstemmed |
Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| title_sort |
Synthesis and biological evaluation of indole derivatives as α-amylase inhibitor |
| publishDate |
2017 |
| container_title |
Bioorganic Chemistry |
| container_volume |
73 |
| container_issue |
|
| doi_str_mv |
10.1016/j.bioorg.2017.06.007 |
| url |
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85021060841&doi=10.1016%2fj.bioorg.2017.06.007&partnerID=40&md5=d9e7c98d5a0decd20b6a24143a22fabd |
| description |
A series of twenty indole hydrazone analogs (1–21) were synthesized, characterized by different spectroscopic techniques such as 1H NMR and EI-MS, and screened for α-amylase inhibitory activity. All analogs showed a variable degree of α-amylase inhibition with IC50 values ranging between 1.66 and 2.65 μM. Nine compounds that are 1 (2.23 ± 0.01 μM), 8 (2.44 ± 0.12 μM), 10 (1.92 ± 0.12 μM), 12 (2.49 ± 0.17 μM), 13 (1.66 ± 0.09 μM), 17 (2.25 ± 0.1 μM), 18 (1.87 ± 0.25 μM), 20 (1.83 ± 0.63 μM), and 19 (1.97 ± 0.02 μM) showed potent α-amylase inhibition when compared with the standard acarbose (1.05 ± 0.29 μM). Other analogs showed good to moderate α-amylase inhibition. The structure activity relationship is mainly focusing on difference of substituents on phenyl part. Molecular docking studies were carried out to understand the binding interaction of the most active compounds. © 2017 Elsevier Inc. |
| publisher |
Academic Press Inc. |
| issn |
452068 |
| language |
English |
| format |
Article |
| accesstype |
|
| record_format |
scopus |
| collection |
Scopus |
| _version_ |
1809677908796506112 |