Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors

Indazole-based Schiff base analogues (1-27) were synthesized by a three-step reaction pathway starting from 1-methyl-1H-indazole-3-carboxylic acid as the basic compound. The structure of the new indazoles was characterized and confirmed by mass spectral analyses as well as NMR spectroscopic data. Al...

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Published in:JOURNAL OF MOLECULAR STRUCTURE
Main Authors: Taha, Muhammad; Gilani, Sadaf Jamal; Kazmi, Imran; Rahim, Fazal; Adalat, Bushra; Ullah, Hayat; Nawaz, Faisal; Wadood, Abdul; Ali, Zarshad; Shah, Syed Adnan Ali; Khan, Khalid Mohammed
Format: Article; Early Access
Language:English
Published: ELSEVIER 2024
Subjects:
Online Access:https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001134539200001
author Taha
Muhammad; Gilani
Sadaf Jamal; Kazmi
Imran; Rahim
Fazal; Adalat
Bushra; Ullah
Hayat; Nawaz
Faisal; Wadood
Abdul; Ali
Zarshad; Shah
Syed Adnan Ali; Khan
Khalid Mohammed
spellingShingle Taha
Muhammad; Gilani
Sadaf Jamal; Kazmi
Imran; Rahim
Fazal; Adalat
Bushra; Ullah
Hayat; Nawaz
Faisal; Wadood
Abdul; Ali
Zarshad; Shah
Syed Adnan Ali; Khan
Khalid Mohammed
Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
Chemistry
author_facet Taha
Muhammad; Gilani
Sadaf Jamal; Kazmi
Imran; Rahim
Fazal; Adalat
Bushra; Ullah
Hayat; Nawaz
Faisal; Wadood
Abdul; Ali
Zarshad; Shah
Syed Adnan Ali; Khan
Khalid Mohammed
author_sort Taha
spelling Taha, Muhammad; Gilani, Sadaf Jamal; Kazmi, Imran; Rahim, Fazal; Adalat, Bushra; Ullah, Hayat; Nawaz, Faisal; Wadood, Abdul; Ali, Zarshad; Shah, Syed Adnan Ali; Khan, Khalid Mohammed
Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
JOURNAL OF MOLECULAR STRUCTURE
English
Article; Early Access
Indazole-based Schiff base analogues (1-27) were synthesized by a three-step reaction pathway starting from 1-methyl-1H-indazole-3-carboxylic acid as the basic compound. The structure of the new indazoles was characterized and confirmed by mass spectral analyses as well as NMR spectroscopic data. All synthesized analogues were screened for their in vitro alpha-glucosidase and alpha-amylase inhibitory activities. All analogues of the series exhibited good inhibitory potentials, with IC50 values ranging from 0.40 +/- 0.01 to 16.20 +/- 0.30 mu M for alpha-glucosidase and 0.70 +/- 0.01 to 17.40 +/- 0.30 mu M for alpha-amylase as compared to the standard drug acarbose (IC50 = 12.90 +/- 0.10 and 12.80 +/- 0.10 mu M, respectively). The most effective analogue of the series is analogue 22 having 3-hydroxyl groups with an IC50 value of 0.40 +/- 0.01 mu M and 0.70 +/- 0.01 mu M for alpha-glucosidase and alpha-amylase, respectively. Structure-activity relationship was carried out, which mainly depends upon the nature, number, position, and electron donating/withdrawing effect of the substituent(s) attached to the phenyl ring. To investigate the binding interaction of the potent analogue with the active site of an enzyme, molecular docking studies were carried out.
ELSEVIER
0022-2860
1872-8014
2024
1300

10.1016/j.molstruc.2023.137189
Chemistry

WOS:001134539200001
https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001134539200001
title Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
title_short Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
title_full Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
title_fullStr Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
title_full_unstemmed Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
title_sort Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors
container_title JOURNAL OF MOLECULAR STRUCTURE
language English
format Article; Early Access
description Indazole-based Schiff base analogues (1-27) were synthesized by a three-step reaction pathway starting from 1-methyl-1H-indazole-3-carboxylic acid as the basic compound. The structure of the new indazoles was characterized and confirmed by mass spectral analyses as well as NMR spectroscopic data. All synthesized analogues were screened for their in vitro alpha-glucosidase and alpha-amylase inhibitory activities. All analogues of the series exhibited good inhibitory potentials, with IC50 values ranging from 0.40 +/- 0.01 to 16.20 +/- 0.30 mu M for alpha-glucosidase and 0.70 +/- 0.01 to 17.40 +/- 0.30 mu M for alpha-amylase as compared to the standard drug acarbose (IC50 = 12.90 +/- 0.10 and 12.80 +/- 0.10 mu M, respectively). The most effective analogue of the series is analogue 22 having 3-hydroxyl groups with an IC50 value of 0.40 +/- 0.01 mu M and 0.70 +/- 0.01 mu M for alpha-glucosidase and alpha-amylase, respectively. Structure-activity relationship was carried out, which mainly depends upon the nature, number, position, and electron donating/withdrawing effect of the substituent(s) attached to the phenyl ring. To investigate the binding interaction of the potent analogue with the active site of an enzyme, molecular docking studies were carried out.
publisher ELSEVIER
issn 0022-2860
1872-8014
publishDate 2024
container_volume 1300
container_issue
doi_str_mv 10.1016/j.molstruc.2023.137189
topic Chemistry
topic_facet Chemistry
accesstype
id WOS:001134539200001
url https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001134539200001
record_format wos
collection Web of Science (WoS)
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