Synthesis of some chalcones derivatives series and their antituberculosis activity

Noviany Noviany; Hasnah Osman; Suriyati Mohamad; Sutopo Hadi; Heri Satria; Buhani Buhani

doi:10.1515/pac-2023-1127

Published online by De Gruyter January 24, 2024

Synthesis of some chalcones derivatives series and their antituberculosis activity

Noviany Noviany , Hasnah Osman , Suriyati Mohamad , Sutopo Hadi , Heri Satria and Buhani Buhani

From the journal Pure and Applied Chemistry

https://doi.org/10.1515/pac-2023-1127

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Abstract

Chalcone is an important biosynthetic precursor, due to the diverse pharmacological activities. The aim of this current study was to synthesize 14 new chalcone derivatives compounds by incorporating p-alkoxyacetophenones with substituted benzaldehydes. Two new series of chalcone derivatives have been synthesized using the alkylation and the base catalysed Claisen-Schmidt condensation. All the synthesized compounds were fully characterized by IR, 1D NMR (¹H and ¹³C NMR) and 2D NMR (COSY, HMQC, HMBC) as well as mass spectrometry analysis. All the synthesized compounds were assayed in vitro for their antituberculosis activities against Mycobacterium tuberculosis strain. Among them, compounds (E)-1-[4-(heptoxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5a), (E)-1-[4-(octyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5b) and (E)-1-[4-(decyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5d) showed good activities with the lowest MIC value of 12.5 μg/mL.

Keywords: antituberculosis activity; chalcones derivatives; Mycobacterium tuberculosis ; VCCA – 2023

Corresponding author: Noviany Noviany, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Lampung, Bandar Lampung 35145, Indonesia, e-mail: noviany@fmipa.unila.ac.id

Article note: A collection of invited papers based on presentations at the Virtual Conference on Chemistry and its Applications 2023 (VCCA-2023).

Funding source: Universitas Lampung

Award Identifier / Grant number: 778/UN26.21/PN/2022

Funding source: Universitas Lampung HETI

Award Identifier / Grant number: 6047/UN26/HK.01.03/2022-2023

Acknowledgments

I would like to forward my appreciation to the technical and laboratory staffs of USM, Mr. Zahari Othman, Ms. Nabiha and Mr. Thaigarajan Parumasivam for their assistance.

Research funding: The authors thank the Higher Education for Technology and Innovation (HETI) Project Implementation Unit (PIU) University of Lampung with agreement numbers of 6047/UN26/HK.01.03/2022-2023 and PT-BLU University of Lampung with agreement numbers of 778/UN26.21/PN/2022.

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Published Online: 2024-01-24

Synthesis of some chalcones derivatives series and their antituberculosis activity

Abstract

Acknowledgments

References

Journal