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New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study

A series of thiazole derivatives 1-4 were synthesized employing simple one-pot reaction pathway and characterized via Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (1H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). The newly synthesized co...

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Main Authors: Abdullah Ripain, Iswatun Hasanah, Darnis, Deny Susanti, Muhamad Bunnori, Noraslinda, Ngah, Nurziana
Format: Article
Language:English
English
Published: Universiti Teknologi Malaysia 2020
Subjects:
QD Chemistry
Online Access:http://irep.iium.edu.my/80658/1/80685_New%202%2C4%2C5-trisubstituted-1%2C3-thiazole%20derivatives.pdf
http://irep.iium.edu.my/80658/2/80685_New%202%2C4%2C5-trisubstituted-1%2C3-thiazole%20derivatives_WOS.pdf
http://irep.iium.edu.my/80658/
https://doi.org/10.11113/jt.v82.13666
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spelling my.iium.irep.806582020-06-18T03:19:47Z http://irep.iium.edu.my/80658/ New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study Abdullah Ripain, Iswatun Hasanah Darnis, Deny Susanti Muhamad Bunnori, Noraslinda Ngah, Nurziana QD Chemistry A series of thiazole derivatives 1-4 were synthesized employing simple one-pot reaction pathway and characterized via Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (1H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). The newly synthesized compounds were evaluated for their in vitro antimicrobial properties against several bacterial strains including Gram-positive and Gram-negative as well as fungus using broth microdilution method. The results revealed that all of the compounds exhibited good activity with a range of MIC values between 1.25-5.0 mg/mL. From the MIC and MBC results, compound 1 exhibited good activities with same MIC value of 1.25 mg/mL and MBC value of 5 mg/mL against B. cereus and S. flexneri. In order to support antimicrobial results, the molecular docking studies were carried out for inhibition of the GlcN-6-P synthase as the target. Out of four compounds underwent for molecular docking studies, 5-acetyl-4-methyl-2-(4-aminobiphenyl)-1,3- thiazole (1) shows the lowest minimum binding energy at -7.32 kcal/mol as compared to 2, 3 and 4 with -7.31, -7.20 and -6.76 kcal/mol, respectively which are in agreement with antimicrobial assay results. In conclusion, 2, 4, 5-trisubstituted- 1,3- thiazole derivatives could be considered as promising antimicrobial in drug discovery candidates. ************************************************************************************** Satu siri terbitan tiazol 1-4 telah disintesis menggunakan tindak balas mudah ‘one-pot’ dan dicirikan dengan kaedah spektroskopi Transformasi Fourier-Inframerah (FTIR), Proton Resonans Magnetik Nukleus (1H NMR) dan Sinar tampak ultraviolet (UV-Vis) serta Kromatografi Jisim Gas-Spektrometer (GC-MS). Sebatian baru yang disintesis ini telah diuji sebagai sebatian yang bercirikan antimikrob secara ‘in-vitro’. Ciri antimikrob ini telah diuji terhadap beberapa strain bakteria iaitu Gram-positif dan Gram-negatif serta fungus menggunakan kaedah kaldu mikrocairan. Keputusan mendapati kesemua sebatian yang diuji (1-4) mempunyai aktiviti di dalam julat nilai MIC diantara 1.25-5.0 mg/mL. Daripada nilai bacaan MIC dan MBC, sebatian 1 menunjukkan aktiviti yang bagus dengan nilai MIC pada 1.25 mg/mL dan MBC pada 5 mg/mL terhadap B. cereus dan S. flexneri. Seterusnya, kajian penyatuan molekul dilakukan ke atas semua sebatian (1-4) untuk merencat GlcN6-P sintase yang digunakan sebagai sebatian sasaran. Diantara empat molekul yang diuji, 5-asetil-4-metil-2-(4-aminobifenil)-1,3-tiazol (1) menunjukkan tenaga pengikatan minimum yang paling rendah iaitu -7.32 kcal/mol berbanding dengan sebatian 2, 3 dan 4 dengan nilai masing-masing iaitu -7.31, -7.20 dan -6.76 kcal/mol selari dengan keputusan ujian antimikrobial. Kesimpulannya, ujian selanjutnya boleh dilakukan ke atas sebatian terbitan 1,3-tiazo berpenggantian-2, 4, 5 di dalam mencari sebatian baru dalam bidang penemuan ubatan baru. Universiti Teknologi Malaysia 2020-02-27 Article PeerReviewed application/pdf en http://irep.iium.edu.my/80658/1/80685_New%202%2C4%2C5-trisubstituted-1%2C3-thiazole%20derivatives.pdf application/pdf en http://irep.iium.edu.my/80658/2/80685_New%202%2C4%2C5-trisubstituted-1%2C3-thiazole%20derivatives_WOS.pdf Abdullah Ripain, Iswatun Hasanah and Darnis, Deny Susanti and Muhamad Bunnori, Noraslinda and Ngah, Nurziana (2020) New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study. Jurnal Teknologi, 82 (2). pp. 61-69. ISSN 0127-9696 E-ISSN 2180–3722 https://doi.org/10.11113/jt.v82.13666
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
English
topic QD Chemistry
spellingShingle QD Chemistry
Abdullah Ripain, Iswatun Hasanah
Darnis, Deny Susanti
Muhamad Bunnori, Noraslinda
Ngah, Nurziana
New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
description A series of thiazole derivatives 1-4 were synthesized employing simple one-pot reaction pathway and characterized via Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (1H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). The newly synthesized compounds were evaluated for their in vitro antimicrobial properties against several bacterial strains including Gram-positive and Gram-negative as well as fungus using broth microdilution method. The results revealed that all of the compounds exhibited good activity with a range of MIC values between 1.25-5.0 mg/mL. From the MIC and MBC results, compound 1 exhibited good activities with same MIC value of 1.25 mg/mL and MBC value of 5 mg/mL against B. cereus and S. flexneri. In order to support antimicrobial results, the molecular docking studies were carried out for inhibition of the GlcN-6-P synthase as the target. Out of four compounds underwent for molecular docking studies, 5-acetyl-4-methyl-2-(4-aminobiphenyl)-1,3- thiazole (1) shows the lowest minimum binding energy at -7.32 kcal/mol as compared to 2, 3 and 4 with -7.31, -7.20 and -6.76 kcal/mol, respectively which are in agreement with antimicrobial assay results. In conclusion, 2, 4, 5-trisubstituted- 1,3- thiazole derivatives could be considered as promising antimicrobial in drug discovery candidates. ************************************************************************************** Satu siri terbitan tiazol 1-4 telah disintesis menggunakan tindak balas mudah ‘one-pot’ dan dicirikan dengan kaedah spektroskopi Transformasi Fourier-Inframerah (FTIR), Proton Resonans Magnetik Nukleus (1H NMR) dan Sinar tampak ultraviolet (UV-Vis) serta Kromatografi Jisim Gas-Spektrometer (GC-MS). Sebatian baru yang disintesis ini telah diuji sebagai sebatian yang bercirikan antimikrob secara ‘in-vitro’. Ciri antimikrob ini telah diuji terhadap beberapa strain bakteria iaitu Gram-positif dan Gram-negatif serta fungus menggunakan kaedah kaldu mikrocairan. Keputusan mendapati kesemua sebatian yang diuji (1-4) mempunyai aktiviti di dalam julat nilai MIC diantara 1.25-5.0 mg/mL. Daripada nilai bacaan MIC dan MBC, sebatian 1 menunjukkan aktiviti yang bagus dengan nilai MIC pada 1.25 mg/mL dan MBC pada 5 mg/mL terhadap B. cereus dan S. flexneri. Seterusnya, kajian penyatuan molekul dilakukan ke atas semua sebatian (1-4) untuk merencat GlcN6-P sintase yang digunakan sebagai sebatian sasaran. Diantara empat molekul yang diuji, 5-asetil-4-metil-2-(4-aminobifenil)-1,3-tiazol (1) menunjukkan tenaga pengikatan minimum yang paling rendah iaitu -7.32 kcal/mol berbanding dengan sebatian 2, 3 dan 4 dengan nilai masing-masing iaitu -7.31, -7.20 dan -6.76 kcal/mol selari dengan keputusan ujian antimikrobial. Kesimpulannya, ujian selanjutnya boleh dilakukan ke atas sebatian terbitan 1,3-tiazo berpenggantian-2, 4, 5 di dalam mencari sebatian baru dalam bidang penemuan ubatan baru.
format Article
author Abdullah Ripain, Iswatun Hasanah
Darnis, Deny Susanti
Muhamad Bunnori, Noraslinda
Ngah, Nurziana
author_facet Abdullah Ripain, Iswatun Hasanah
Darnis, Deny Susanti
Muhamad Bunnori, Noraslinda
Ngah, Nurziana
author_sort Abdullah Ripain, Iswatun Hasanah
title New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
title_short New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
title_full New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
title_fullStr New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
title_full_unstemmed New 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
title_sort new 2,4,5-trisubstituted-1,3-thiazole derivatives: synthesis, in vitro antimicrobial activity and in silico study
publisher Universiti Teknologi Malaysia
publishDate 2020
url http://irep.iium.edu.my/80658/1/80685_New%202%2C4%2C5-trisubstituted-1%2C3-thiazole%20derivatives.pdf
http://irep.iium.edu.my/80658/2/80685_New%202%2C4%2C5-trisubstituted-1%2C3-thiazole%20derivatives_WOS.pdf
http://irep.iium.edu.my/80658/
https://doi.org/10.11113/jt.v82.13666
_version_ 1672610196828979200
score 13.211869

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