Bis-Thiourea Bearing Aryl and Amino Acids Side Chains and Their Antibacterial Activities

Zullkiplee, Wan Sharifatun Handayani Wan; Halim, Ainaa Nadiah Abd; Ngaini, Zainab; Ariff, Maya Asyikin Mohd; Hussain, Hasnain

doi:10.1080/10426507.2013.858250

Cited by 25 publications

(12 citation statements)

References 6 publications

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“…10 The presence of three thiourea moieties offers more reactive C=O, C=S and NH moieties to the surface of E. coli. 17 The structure activity relationship of 7-9 bearing a chloro substituent in the ortho, meta and …”

Section: Antibacterial Activitymentioning

confidence: 99%

Bacteriostatic activities ofN-substituted tris-thioureas bearing amino acid and aniline substituents

Zullkiplee

Ariff

Hussain

et al. 2016

Phosphorus, Sulfur, and Silicon and the Related Elements

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A series of tri-substituted thiourea derivatives were synthesized by the reaction of 1,3,5-triacetylbenzoyl isothiocyanate with aminoacids and aniline derivatives. All thiourea derivatives were characterized by FT-IR, 1 H and 13 C NMR spectroscopy. Antibacterial activities against wild-type Escherichia coli American Type Culture Collection 8739 were determined by use of Downloaded by [University of Nebraska, Lincoln] at 07:04 01 June 2016 ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 2 the turbidimetric method to evaluate the effect of varying amino groups on the synthesized thioureas. Tris-thiourea derivatives bearing ortho-chloroaryl substituents showed excellent antibacterial activity against E. coli with minimal inhibitory concentration (MIC) of 96 ppm. The optimum inhibition was dependent on the type of amines and the position of the halogen in aniline.

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Section: Antibacterial Activitymentioning

confidence: 99%

Bacteriostatic activities ofN-substituted tris-thioureas bearing amino acid and aniline substituents

Zullkiplee

Ariff

Hussain

et al. 2016

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Our previous studies reported on thiourea bearing aromatic amine with excellent antibacterial properties [6,17]. In continuation to our previous work, in this article, we report on the synthesis of thiourea compounds with hexachlorocyclotriphosphazene as a hexasubstituted precursor in a typical one-pot reaction system [11].…”

Section: Introductionmentioning

confidence: 96%

“…Compounds a-b showed binding free energy of −4.5 kcal/mol and −4.7 kcal/mol, respectively. Based on the importance properties of the aromatic group in earlier studies [6][7][8], the optimisation study via molecular docking was carried out to evaluate the binding free energy of a-b in comparison to the predicted phenyl thiourea a-b. The presence of another aromatic group in a-b demonstrated for a higher binding affinity with the free energy of −5.9 kcal/mol and −6.3 kcal/mol, respectively.…”

Section: Molecular Docking Design and Optimisationmentioning

confidence: 99%

“…Multisubstituted thioureas have gained more interest among researchers due to the increase of their pharmaceutical properties. Our recent studies on thiourea reported that compounds that consist of more than one thiourea moiety possess better antimicrobial activities [6][7][8]. It was due to the presence of more active sites of thiourea moieties containing C=S, C=O, and N-H groups, which are easily protonated under acidic condition and interacted with the carboxyl and phosphate groups of the bacterial surfaces, thus enhancing the biological activities [7].…”

Section: Introductionmentioning

confidence: 99%

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One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

Ngaini

Zulkiplee

Halim

2017

Journal of Chemistry

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In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives a-f were formed in the presence of cyclotriphosphazene moieties in good yields (53-82%). The structures of a-f were characterized by elemental analysis and FTIR, 1 H, 13 C, and 31 P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea a-b in comparison to the predicted phenyl thiourea a-b and the targeted a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea a is able to give higher binding affinity of −7.5 kcal/mol compared to a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea a-b (−4.5 kcal/mol and −4.7 Kcal/mol).

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“…Amongst this class of compounds, benzoyl derivatives of thiourea have gained a great deal of importance in the present day. Thiourea linkages have contributed greatly to the observed enhancement in various activities [3], including antiviral [4], antibacterial [5, 6], antifungal [7], antitubercular [8, 9], herbicidal [10], insecticidal [11], pharmacological properties [12], as chelating agents [13, 14] and as anticancer compounds [15]. In addition, benzoyl thiourea derivatives have often been used in analytical and biological applications [16, 17].…”

Section: Introductionmentioning

confidence: 99%

A comparative study of the metal binding behavior of alanine based bis-thiourea isomers

Fakhar

Yamin

Hasbullah

2017

Chemistry Central Journal

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Two new symmetrical bis-thiourea, 2,2′-[{(terephthaloylbis(azanediyl)bis(carbonothioyl) bis(azanediyl)}dipropanoic acid] (1A) and 3,3′-[{(terephthaloylbis(azanediyl)bis (carbonothioyl)bis(azanediyl)} dipropanoic acid] (1B) were synthesized by the reaction of terephthaloyl chloride with α- and β-alanine in good yields. Their binding properties were investigated with various metal cations using UV–Vis titration experiments. Both isomers exhibited effective binding with Ag+, Cu2+, Hg2+, Pb2+, Fe2+ and Fe3+ cations. However, in the presence of other cations, such as Na+, Ni2+, Co2+, Cd2+, Zn2+, Mn2+, Mg2+, Ca2+, Sn2+, Al3+, and anions tetrabutylammonium Cl− and H2PO4 −, no interaction occurred. Both isomers displayed similar trends towards binding with metal cations.

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Bis-Thiourea Bearing Aryl and Amino Acids Side Chains and Their Antibacterial Activities

Cited by 25 publications

References 6 publications

Bacteriostatic activities ofN-substituted tris-thioureas bearing amino acid and aniline substituents

Bacteriostatic activities ofN-substituted tris-thioureas bearing amino acid and aniline substituents

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

A comparative study of the metal binding behavior of alanine based bis-thiourea isomers

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