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Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid

This study presents the synthesis of a series of methoxybenzoylthiourea amino acid derivatives. The compounds were obtained from the reactions between 2/3/4-methoxybenzoyl isothiocyanate with threonine. All of the compounds were characterized via mass spectrometry, 1H and 13C NMR spectrometry, UV-Vi...

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Main Authors: Mohd Yusof, Mohd Sukeri, Ramli, R., Che Soh, Siti Kamilah, Ngah, Nurziana
Format: Article
Language:English
Published: World Academy of Science, Engineering and Technology 2019
Subjects:
QD Chemistry
Online Access:http://irep.iium.edu.my/77587/1/Synthesis-Characterization-and-Antibacterial-Screening-of-3-Hydroxy-2-3-234-MethoxybenzoylThioureidoButyric-Acid.pdf
http://irep.iium.edu.my/77587/
https://publications.waset.org/10009921/pdf
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spelling my.iium.irep.775872020-02-26T19:56:05Z http://irep.iium.edu.my/77587/ Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid Mohd Yusof, Mohd Sukeri Ramli, R. Che Soh, Siti Kamilah Ngah, Nurziana QD Chemistry This study presents the synthesis of a series of methoxybenzoylthiourea amino acid derivatives. The compounds were obtained from the reactions between 2/3/4-methoxybenzoyl isothiocyanate with threonine. All of the compounds were characterized via mass spectrometry, 1H and 13C NMR spectrometry, UV-Vis spectrophotometer and FT-IR spectroscopy. Mass spectra for all of the compounds showed the presence of molecular ion [M]+ peaks at m/z 312, which are in agreement to the calculated molecular weight. For 1H NMR spectra, the presence of OCH3, C=S-NH and C=O-NH protons were observed within the range of δH 3.8-4.0 ppm, 11.1-11.5 ppm and 10.0-11.5 ppm, respectively. 13C NMR spectra in all compounds displayed the presence of OCH3, C=O-NH, C=O-OH and C=S carbon resonances within range of δC 55.0-57.0 ppm, 165.0- 168.0 ppm, 170.0-171.0 ppm and 180.0-182.0 ppm, respectively. In UV spectra, two absorption bands have been observed and both were assigned to the n-π* and π-π* transitions. Six vibrational modes of v(N-H), v(O-H), v(C=O-OH), v(C=O-NH), v(C=C) aromatic and v(C=S) appeared in the FT-IR spectra within the range of 3241-3467 cm-1, 2976-3302 cm-1, 1720-1768 cm-1, 1655-1672 cm-1, 1519-1525 cm-1 and 754-763 cm-1, respectively. The antibacterial activity for all of the compounds was screened against Staphylococcus aureus, Staphylococcus epidermidis, Salmonella typhimurium and Escherichia coli. However, no activity was observed. World Academy of Science, Engineering and Technology 2019 Article PeerReviewed application/pdf en http://irep.iium.edu.my/77587/1/Synthesis-Characterization-and-Antibacterial-Screening-of-3-Hydroxy-2-3-234-MethoxybenzoylThioureidoButyric-Acid.pdf Mohd Yusof, Mohd Sukeri and Ramli, R. and Che Soh, Siti Kamilah and Ngah, Nurziana (2019) Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid. International Journal of Chemical and Molecular Engineering, 13 (1). pp. 1-4. E-ISSN 1307-6892 https://publications.waset.org/10009921/pdf 10.5281/zenodo.3461810
institution Universiti Islam Antarabangsa Malaysia
building IIUM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider International Islamic University Malaysia
content_source IIUM Repository (IREP)
url_provider http://irep.iium.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Mohd Yusof, Mohd Sukeri
Ramli, R.
Che Soh, Siti Kamilah
Ngah, Nurziana
Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
description This study presents the synthesis of a series of methoxybenzoylthiourea amino acid derivatives. The compounds were obtained from the reactions between 2/3/4-methoxybenzoyl isothiocyanate with threonine. All of the compounds were characterized via mass spectrometry, 1H and 13C NMR spectrometry, UV-Vis spectrophotometer and FT-IR spectroscopy. Mass spectra for all of the compounds showed the presence of molecular ion [M]+ peaks at m/z 312, which are in agreement to the calculated molecular weight. For 1H NMR spectra, the presence of OCH3, C=S-NH and C=O-NH protons were observed within the range of δH 3.8-4.0 ppm, 11.1-11.5 ppm and 10.0-11.5 ppm, respectively. 13C NMR spectra in all compounds displayed the presence of OCH3, C=O-NH, C=O-OH and C=S carbon resonances within range of δC 55.0-57.0 ppm, 165.0- 168.0 ppm, 170.0-171.0 ppm and 180.0-182.0 ppm, respectively. In UV spectra, two absorption bands have been observed and both were assigned to the n-π* and π-π* transitions. Six vibrational modes of v(N-H), v(O-H), v(C=O-OH), v(C=O-NH), v(C=C) aromatic and v(C=S) appeared in the FT-IR spectra within the range of 3241-3467 cm-1, 2976-3302 cm-1, 1720-1768 cm-1, 1655-1672 cm-1, 1519-1525 cm-1 and 754-763 cm-1, respectively. The antibacterial activity for all of the compounds was screened against Staphylococcus aureus, Staphylococcus epidermidis, Salmonella typhimurium and Escherichia coli. However, no activity was observed.
format Article
author Mohd Yusof, Mohd Sukeri
Ramli, R.
Che Soh, Siti Kamilah
Ngah, Nurziana
author_facet Mohd Yusof, Mohd Sukeri
Ramli, R.
Che Soh, Siti Kamilah
Ngah, Nurziana
author_sort Mohd Yusof, Mohd Sukeri
title Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
title_short Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
title_full Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
title_fullStr Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
title_full_unstemmed Synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
title_sort synthesis, characterization and antibacterial screening of 3-hydroxy-2-[3-(2/3/4-methoxybenzoyl) thioureido] butyric acid
publisher World Academy of Science, Engineering and Technology
publishDate 2019
url http://irep.iium.edu.my/77587/1/Synthesis-Characterization-and-Antibacterial-Screening-of-3-Hydroxy-2-3-234-MethoxybenzoylThioureidoButyric-Acid.pdf
http://irep.iium.edu.my/77587/
https://publications.waset.org/10009921/pdf
_version_ 1662753784919490560
score 13.211869

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