PMID- 37478545
OWN - NLM
STAT- MEDLINE
DCOM- 20230814
LR  - 20230814
IS  - 1090-2120 (Electronic)
IS  - 0045-2068 (Linking)
VI  - 139
DP  - 2023 Oct
TI  - Synthesis, biological evaluation and molecular modelling of 
      3-Formyl-6-isopropylchromone derived thiosemicarbazones as alpha-glucosidase 
      inhibitors.
PG  - 106739
LID - S0045-2068(23)00400-5 [pii]
LID - 10.1016/j.bioorg.2023.106739 [doi]
AB  - Type-2 Diabetes Mellitus (T2DM) is one of the most common metabolic disorders in 
      the world and over the past three decades its incidence has increased 
      drastically. alpha-Glucosidase inhibitors are used to control the hyperglycemic 
      affect of T2DM. Herein, we report the synthesis, alpha-glucosidase inhibition, 
      structure activity relationship, pharmacokinetics and docking analysis of various 
      novel chromone based thiosemicarbazones 3(a-r). The derivatives displayed potent 
      activity against alpha-glucosidase with IC(50) in range of 
      0.11 +/- 0.01-79.37 +/- 0.71 microM. Among all the synthesized compounds, 3a 
      (IC(50) = 0.17 +/- 0.026 microM), 3 g (IC(50) = 0.11 +/- 0.01 microM), 3n 
      (IC(50) = 0.55 +/- 0.02 microM), and 3p (IC(50) = 0.43 +/- 0.025 microM) displayed higher 
      inhibitory activity as compared to the standard, acarbose. Moreover, we have 
      developed a statistically significant 2D-QSAR model (R(2)(tr):0.9693; F: 50.4647 
      and Q(2)(LOO):0.9190), which can be used in future to further design potent 
      thiosemicarbazones as inhibitors of alpha-glucosidase.
CI  - Copyright (c) 2023 Elsevier Inc. All rights reserved.
FAU - Basri, Rabia
AU  - Basri R
AD  - Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, 
      Pakistan.
FAU - Ullah, Saeed
AU  - Ullah S
AD  - Natural and Medical Sciences Research Centre, University of Nizwa, P.O. Box 33, 
      PC 616, Birkat Al Mauz, Nizwa, Sultanate of Oman.
FAU - Khan, Ajmal
AU  - Khan A
AD  - Natural and Medical Sciences Research Centre, University of Nizwa, P.O. Box 33, 
      PC 616, Birkat Al Mauz, Nizwa, Sultanate of Oman.
FAU - Mali, Suraj N
AU  - Mali SN
AD  - Department of Pharmaceutical Science and Technology, Birla Institute of 
      Technology, Mesra 835215, India.
FAU - Abchir, Oussama
AU  - Abchir O
AD  - Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M'Sik, 
      Hassan II University of Casablanca, Casablanca B.P 7955, Morocco.
FAU - Chtita, Samir
AU  - Chtita S
AD  - Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M'Sik, 
      Hassan II University of Casablanca, Casablanca B.P 7955, Morocco.
FAU - El-Gokha, Ahmed
AU  - El-Gokha A
AD  - Chemistry Department, Faculty of Science, Menoufia University Menoufia, Egypt.
FAU - Taslimi, Parham
AU  - Taslimi P
AD  - Department of Biotechnology, Faculty of Science, Bartin University, 74100 Bartin, 
      Turkey.
FAU - Binsaleh, Ammena Y
AU  - Binsaleh AY
AD  - Department of Pharmacy Practice, College of Pharmacy, Princess Nourah bint 
      Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi Arabia.
FAU - El-Kott, Attalla F
AU  - El-Kott AF
AD  - Department of Biology, College of Science, King Khalid University, Abha 61421, 
      Saudi Arabia; Department of Zoology, College of Science, Damanhour University, 
      Damanhour 22511, Egypt.
FAU - Al-Harrasi, Ahmed
AU  - Al-Harrasi A
AD  - Natural and Medical Sciences Research Centre, University of Nizwa, P.O. Box 33, 
      PC 616, Birkat Al Mauz, Nizwa, Sultanate of Oman. Electronic address: 
      aharrasi@unizwa.edu.om.
FAU - Shafiq, Zahid
AU  - Shafiq Z
AD  - Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, 
      Pakistan; Department of Pharmaceutical & Medicinal Chemistry, An der Immenburg 4, 
      D-53121 Bonn, Germany. Electronic address: zahidshafiq@bzu.edu.pk.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20230717
PL  - United States
TA  - Bioorg Chem
JT  - Bioorganic chemistry
JID - 1303703
RN  - 0 (Glycoside Hydrolase Inhibitors)
RN  - 0 (Thiosemicarbazones)
RN  - EC 3.2.1.20 (alpha-Glucosidases)
SB  - IM
MH  - Humans
MH  - Glycoside Hydrolase Inhibitors/chemistry
MH  - *Thiosemicarbazones/pharmacology
MH  - alpha-Glucosidases/metabolism
MH  - Molecular Docking Simulation
MH  - Structure-Activity Relationship
MH  - *Diabetes Mellitus, Type 2/drug therapy/metabolism
MH  - Molecular Structure
OTO - NOTNLM
OT  - Chromene
OT  - Diabetes Mellitus
OT  - Molecular Docking
OT  - Thiosemicarbazones
OT  - alpha-glucosidase inhibition
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- 2023/07/22 10:42
MHDA- 2023/08/14 06:42
CRDT- 2023/07/21 18:02
PHST- 2023/06/12 00:00 [received]
PHST- 2023/07/11 00:00 [revised]
PHST- 2023/07/15 00:00 [accepted]
PHST- 2023/08/14 06:42 [medline]
PHST- 2023/07/22 10:42 [pubmed]
PHST- 2023/07/21 18:02 [entrez]
AID - S0045-2068(23)00400-5 [pii]
AID - 10.1016/j.bioorg.2023.106739 [doi]
PST - ppublish
SO  - Bioorg Chem. 2023 Oct;139:106739. doi: 10.1016/j.bioorg.2023.106739. Epub 2023 
      Jul 17.