Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones

Researchers have put so much effort in N-acylhydrazones recently due to their biological activities such as antibacterial, antitumor, anticancer, antioxidant and anti-inflammatory. A series of new N-acylhydrazone derivatives SB 1- SB 10 were synthesized in yields ranging from 52 to 78% through the r...

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Main Author: Khong, Pek Yao
Format: Final Year Project / Dissertation / Thesis
Published: 2023
Subjects:
Online Access:http://eprints.utar.edu.my/5411/
http://eprints.utar.edu.my/5411/1/fyp_CE_2023_KPY.pdf
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author Khong, Pek Yao
author_facet Khong, Pek Yao
author_sort Khong, Pek Yao
building UTAR Institutional Repository
collection Online Access
description Researchers have put so much effort in N-acylhydrazones recently due to their biological activities such as antibacterial, antitumor, anticancer, antioxidant and anti-inflammatory. A series of new N-acylhydrazone derivatives SB 1- SB 10 were synthesized in yields ranging from 52 to 78% through the reactions of carboxylic acid hydrazide with a variety of substituted benzaldehydes. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C NMR, DEPT, NOE, HMQC and HMBC spectral data. From the relative configuration of imine double bond and the conformation of CONH bond of synthesized compounds, the C=N double bonds of N-acylhydrazones showed (E)-configuration, while the NMR data of all synthesized N-acylhydrazones indicated the existence of cis-/trans- conformers for each compound in DMSO-d6. In N-acylhydrazones SB 1 – SB 5, the signals of the cis- and trans amide conformers coalesced as the temperature increased between 298 and 373 K. The synthesized compounds were evaluated for their antibacterial activities against three microbial strains which were two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and one Gram-negative ii bacteria (Pseudomonas aeruginosa). The result suggested that SB 1 - SB 9 exhibited poor antibacterial activities against all tested bacteria strain. Particularly, compound SB 10 (2- OH, 4NEt2) showed moderate antibacterial activity against Gram-negative bacteria Pseudomonas aeruginosa at MIC value of 62.5 µg/mL
first_indexed 2025-11-15T19:38:02Z
format Final Year Project / Dissertation / Thesis
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institution Universiti Tunku Abdul Rahman
institution_category Local University
last_indexed 2025-11-15T19:38:02Z
publishDate 2023
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spelling utar-54112023-09-11T13:29:00Z Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones Khong, Pek Yao Q Science (General) QD Chemistry Researchers have put so much effort in N-acylhydrazones recently due to their biological activities such as antibacterial, antitumor, anticancer, antioxidant and anti-inflammatory. A series of new N-acylhydrazone derivatives SB 1- SB 10 were synthesized in yields ranging from 52 to 78% through the reactions of carboxylic acid hydrazide with a variety of substituted benzaldehydes. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C NMR, DEPT, NOE, HMQC and HMBC spectral data. From the relative configuration of imine double bond and the conformation of CONH bond of synthesized compounds, the C=N double bonds of N-acylhydrazones showed (E)-configuration, while the NMR data of all synthesized N-acylhydrazones indicated the existence of cis-/trans- conformers for each compound in DMSO-d6. In N-acylhydrazones SB 1 – SB 5, the signals of the cis- and trans amide conformers coalesced as the temperature increased between 298 and 373 K. The synthesized compounds were evaluated for their antibacterial activities against three microbial strains which were two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and one Gram-negative ii bacteria (Pseudomonas aeruginosa). The result suggested that SB 1 - SB 9 exhibited poor antibacterial activities against all tested bacteria strain. Particularly, compound SB 10 (2- OH, 4NEt2) showed moderate antibacterial activity against Gram-negative bacteria Pseudomonas aeruginosa at MIC value of 62.5 µg/mL 2023-01 Final Year Project / Dissertation / Thesis NonPeerReviewed application/pdf http://eprints.utar.edu.my/5411/1/fyp_CE_2023_KPY.pdf Khong, Pek Yao (2023) Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones. Final Year Project, UTAR. http://eprints.utar.edu.my/5411/
spellingShingle Q Science (General)
QD Chemistry
Khong, Pek Yao
Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones
title Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones
title_full Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones
title_fullStr Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones
title_full_unstemmed Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones
title_short Synthesis, characterization, conformational study and antibacterial activity of N-acylhydrazones
title_sort synthesis, characterization, conformational study and antibacterial activity of n-acylhydrazones
topic Q Science (General)
QD Chemistry
url http://eprints.utar.edu.my/5411/
http://eprints.utar.edu.my/5411/1/fyp_CE_2023_KPY.pdf