PMID- 36528921
OWN - NLM
STAT- MEDLINE
DCOM- 20230120
LR  - 20230201
IS  - 1090-2120 (Electronic)
IS  - 0045-2068 (Linking)
VI  - 131
DP  - 2023 Feb
TI  - Synthesis of new phenoxymethylcoumarin clubbed 4-arylthiazolylhydrazines as 
      alpha-glucosidase inhibitors and their kinetics and molecular docking studies.
PG  - 106302
LID - S0045-2068(22)00708-8 [pii]
LID - 10.1016/j.bioorg.2022.106302 [doi]
AB  - The current studies mainly demonstrate the coumarin based azomethine-clubbed 
      thiazoles synthesis and their in-vitro evaluation for the first time against 
      alpha-glucosidase. Due to the catalytic role of alpha-glucosidase, it has become a 
      precise target for the treatment of type diabetes mellitus (T2DM). The high rate 
      of prevalence of diabetes and its associated health related problems led us to 
      scrutinize the anti-diabetic capability of the synthesized thiazole derivatives 
      (6a-6k). The anticipated structures of prepared compounds were confirmed through 
      FT-IR and NMR spectroscopic methods. All the compounds showed several times 
      potent activity than the standard drug, acarbose (IC(50) = 873.34 +/- 1.67 microM) 
      against alpha-glucosidase with IC(50) values in range of 
      0.87 +/- 0.02-322.61 +/- 1.14 microM. The compound 6k displayed the highest anti-diabetic 
      activity (IC(50) = 1.88 +/- 0.03 microM). Kinetic study revealed that these are 
      competitive inhibitors for alpha-glucosidase. The mode of binding of the synthesized 
      molecules were further evaluated by molecular docking, which reflects the 
      importance of azomethine group in protein-ligand interaction. The docking scores 
      are complementary with the IC(50) values of compounds while the interaction 
      pattern of the compounds clearly demonstrates their structure-activity 
      relationship. Current study reported medicinal importance of thiazole derivative 
      as future drug candidates for the management of Type 2 Diabetes Mellitus (T2DM).
CI  - Copyright (c) 2022. Published by Elsevier Inc.
FAU - Ul Ain, Qurat
AU  - Ul Ain Q
AD  - Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
FAU - Saeed, Aamer
AU  - Saeed A
AD  - Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. 
      Electronic address: asaeed@qau.edu.pk.
FAU - Khan, Ajmal
AU  - Khan A
AD  - Natural and Medical Sciences Research Center, University of Nizwa, 
      Birkat-ul-Mouz, 616, Nizwa, Oman.
FAU - Ahmed, Atteeque
AU  - Ahmed A
AD  - Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
FAU - Ullah, Saeed
AU  - Ullah S
AD  - Natural and Medical Sciences Research Center, University of Nizwa, 
      Birkat-ul-Mouz, 616, Nizwa, Oman; H. E. J. Research Institute of Chemistry, 
      International Center for Chemical and Biological Sciences, University of Karachi, 
      Karachi 75270, Pakistan; Department of Chemistry, Khawaja Farid University of 
      Engineering and Information Technology, Rahim Yar Khan, Pakistan.
FAU - Ahsan Halim, Sobia
AU  - Ahsan Halim S
AD  - Natural and Medical Sciences Research Center, University of Nizwa, 
      Birkat-ul-Mouz, 616, Nizwa, Oman.
FAU - Irfan, Madiha
AU  - Irfan M
AD  - H. E. J. Research Institute of Chemistry, International Center for Chemical and 
      Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
FAU - Tehzeeb, Arfa
AU  - Tehzeeb A
AD  - Department of Pharmacy, Quaid-i-Azam University, Islamabad 45320, Pakistan.
FAU - El-Seedi, Hesham R
AU  - El-Seedi HR
AD  - School of Food and Biological Engineering, Jiangsu University, Zhenjiang 212013, 
      China; International Joint Research Laboratory of Intelligent Agriculture and 
      Agri-Products Processing, Jiangsu Education Department, Jiangsu University, 
      Zhenjiang, China; Department of Chemistry, Faculty of Science, Menoufia 
      University, Shebin El-Kom 32512, Egypt.
FAU - Bin Muhsinah, Abdullatif
AU  - Bin Muhsinah A
AD  - Department of Pharmacognosy, College of Pharmacy, King Khalid University, Abha 
      62529, Saudi Arabia.
FAU - Al-Harrasi, Ahmed
AU  - Al-Harrasi A
AD  - Natural and Medical Sciences Research Center, University of Nizwa, 
      Birkat-ul-Mouz, 616, Nizwa, Oman. Electronic address: aharrasi@unizwa.edu.om.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20221128
PL  - United States
TA  - Bioorg Chem
JT  - Bioorganic chemistry
JID - 1303703
RN  - 0 (Glycoside Hydrolase Inhibitors)
RN  - 0 (azomethine)
RN  - EC 3.2.1.20 (alpha-Glucosidases)
RN  - 0 (Thiazoles)
SB  - IM
MH  - Humans
MH  - *Glycoside Hydrolase Inhibitors/chemistry
MH  - Molecular Docking Simulation
MH  - Molecular Structure
MH  - *Diabetes Mellitus, Type 2/drug therapy
MH  - alpha-Glucosidases/metabolism
MH  - Spectroscopy, Fourier Transform Infrared
MH  - Structure-Activity Relationship
MH  - Kinetics
MH  - Thiazoles/chemistry
OTO - NOTNLM
OT  - Molecular docking
OT  - Phenoxymethylcoumarin clubbed 4-arylthiazolylhydrazines
OT  - Synthesis
OT  - alpha-glucosidase
COIS- Declaration of Competing Interest The authors declare that they have no known 
      competing financial interests or personal relationships that could have appeared 
      to influence the work reported in this paper.
EDAT- 2022/12/19 06:00
MHDA- 2023/01/21 06:00
CRDT- 2022/12/18 18:13
PHST- 2022/09/12 00:00 [received]
PHST- 2022/11/12 00:00 [revised]
PHST- 2022/11/23 00:00 [accepted]
PHST- 2022/12/19 06:00 [pubmed]
PHST- 2023/01/21 06:00 [medline]
PHST- 2022/12/18 18:13 [entrez]
AID - S0045-2068(22)00708-8 [pii]
AID - 10.1016/j.bioorg.2022.106302 [doi]
PST - ppublish
SO  - Bioorg Chem. 2023 Feb;131:106302. doi: 10.1016/j.bioorg.2022.106302. Epub 2022 
      Nov 28.