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Synthesis of Novel Triazinoindole-Based Thiourea Hybrid: A Study on α-Glucosidase Inhibitors and Their Molecular Docking

Taha M 1 , Alshamrani FJ 2 , Rahim F 3 , Hayat S 4 , Ullah H 5 , Zaman K 6 Show all authors , Imran S 7 , Khan KM 8 , Naz F 9

Affiliations 

  • 1 Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia. mtaha@iau.edu.sa
  • 2 Neurology Department, King Fahad hospital of University, Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 34211, Saudi Arabia. Fshamrani@uod.edu.sa
  • 3 Department of Chemistry, Hazara University, Mansehra-21300, Khyber Pakhtunkhwa, Pakistan. fazalstar@gmail.com
  • 4 Department of Chemistry, Hazara University, Mansehra-21300, Khyber Pakhtunkhwa, Pakistan. shawkathayat866@yahoo.com
  • 5 Department of Chemistry, Hazara University, Mansehra-21300, Khyber Pakhtunkhwa, Pakistan. ayaanwazir366@gmail.com
  • 6 Department of Chemistry, Hazara University, Mansehra-21300, Khyber Pakhtunkhwa, Pakistan. khalidchemist69@yahoo.com
  • 7 Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D.E., Malaysia. imran@isiswa.uitm.edu.my
  • 8 H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. khalid.khan@iccs.edu
  • 9 Department of Chemistry, Jinnah University for Women, 5-C, Nazimabad, Karachi-74600, Pakistan. farzanahej@yahoo.com
Molecules, 2019 Oct 23;24(21).
PMID: 31652777 DOI: 10.3390/molecules24213819

Abstract

A new class of triazinoindole-bearing thiosemicarbazides (1-25) was synthesized and evaluated for α-glucosidase inhibitory potential. All synthesized analogs exhibited excellent inhibitory potential, with IC50 values ranging from 1.30 ± 0.01 to 35.80 ± 0.80 µM when compared to standard acarbose (an IC50 value of 38.60 ± 0.20 µM). Among the series, analogs 1 and 23 were found to be the most potent, with IC50 values of 1.30 ± 0.05 and 1.30 ± 0.01 µM, respectively. The structure-activity relationship (SAR) was mainly based upon bringing about different substituents on the phenyl rings. To confirm the binding interactions, a molecular docking study was performed.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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