Synthesis and in vitro study of benzofuran hydrazone derivatives as novel alpha-amylase inhibitor

Muhammad Taha, Syed Adnan Ali Shah, Syahrul Imran, Muhammad Afifi, Sridevi Chigurupati, Manikandan Selvaraj, Fazal Rahim, Hayat Ullah, Khalid Zaman, Shantini Vijayabalan

Research output: Contribution to journalArticleResearchpeer-review

19 Citations (Scopus)

Abstract

The α-amylase acts as attractive target to treat type-2 diabetes mellitus. Therefore in discovering a small molecule as α-amylase inhibitor, we have synthesized benzofuran carbohydrazide analogs (1–25), characterized through different spectroscopic techniques such as 1HNMR and EI-MS. All screened analog shows good α-amylase inhibitory potentials with IC50 value ranging between 1.078 ± 0.19 and 2.926 ± 0.05 µM when compared with acarbose having IC50 = 0.62 ± 0.22 µM. Only nine analogs among the series such as analogs 3, 5, 7, 8, 10, 12, 21, 23 and 24 exhibit good inhibitory potential with IC50 values 1.644 ± 0.128, 1.078 ± 0.19, 1.245 ± 0.25, 1.843 ± 0.19, 1.350 ± 0.24, 1.629 ± 0.015, 1.353 ± 0.232, 1.359 ± 0.119 and 1.488 ± 0.07 µM when compare with standard drug acarbose. All other analogs showed good to moderate α-amylase inhibitory potentials. The SAR study was conducted on the basis of substituent difference at the phenyl ring. The binding interaction between analogs and active site of enzyme was confirmed by docking studies.

Original languageEnglish
Pages (from-to)78-85
Number of pages8
JournalBioorganic Chemistry
Volume75
DOIs
Publication statusPublished - Dec 2017
Externally publishedYes

Keywords

  • Benzofuran-2-carbohydrazide
  • Molecular docking
  • SAR
  • Synthesis
  • α-Amylase

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