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\begin{document}


\def\RunningAuthor{Hawraa Mohammed Sadiq et al.}
\firstPage{2993}
\articleType{Original Article}
\receivedDate{05 Mar 2020}
\acceptedDate{05 May 2020}
\revisedDate{05 Apr 2020}
\journalVolume{2020, 11}
\journalIssue{3}
\journalDoi{ijrps.v11i3.2393}
\copyrightYear{2020}
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\title{Schiff bases derivatives: synthesis, identification, and antibacterial activity against pathogenic bacteria isolated from patients infected with wound infection}
\author{Hawraa~Mohammed~Sadiq\textsuperscript{*}\textsuperscript{1},  
            Hutham~Mahmood~Yousif~Al-Labban\textsuperscript{1}, 
            Ahmed~Abduljabbar~Jaloob~Aljanaby\textsuperscript{2}~\\[5pt]{\textsuperscript{1}Department of Chemistry, University of Kufa, Faculty of Science, Iraq }~\\{\textsuperscript{2}Department of Biology, University of Kufa, Faculty of Science,  Iraq }}

\begin{abstract}
Schiff bases derivatives are one of the most important compounds that have been used in many biological applications such as antimicrobial activity. Pseudomonas aeruginosa and Staphylococcus aureus are two of the most important pathogenic bacteria that cause wound infection in Iraq and many developing countries. This research involves a synthesis of some Schiff bases compounds [A\ensuremath{_{1\ }} {\textendash} A\ensuremath{_{3}}] that were prepared from the condensation of [4-chlorobenzaldehyde, 4-bromobenzaldehyde, and 4-hydroxybenzaldehyde] in absolute ethanol. All of these compounds are characterized by [FTIR] spectroscopy. The antibacterial activity test was done according to agar well diffusion method for all derivative compounds with a concentration of 100 mg/ml and 200 mg/ml for each compound. The derivative compound A3 with a concentration of 200 mg/ml had an excellent antibacterial effect against Pseudomonas aeruginosa  and Staphylococcus aureus  with a diameter of inhibition zone of 18.417 \ensuremath{\pm} 0.54645 and 16.000 \ensuremath{\pm} 0.57735, respectively. Schiff bases derivatives synthesis compounds in this study (A1 and A2) can be considered as suitable antibacterial materials and can be used as raw materials to the synthesis of new ointment. 
\end{abstract}\def\keywordstitle{Keywords}

\begin{keywords}4-methoxyaniline,\newline Schiff bases,\newline Pseudomonas aeruginosa,\newline Staphylococcus aureus Wound infection,\newline Iraq
\end{keywords}
\twocolumn[ \maketitle {\printKwdAbsBox}]
\makeatletter{\raggedright\textsuperscript{*}Corresponding Author\par Name:\ Hawraa~Mohammed~Sadiq~\\ Phone:\ ~\\  Email:\ hawraam.hmeidi@uokufa.edu.iq
        \par}\vspace*{-11pt}\hrulefill\par{\fontsize{12}{14}\selectfont ISSN: 0975-7538}\par% 
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        \makeatother
        
    
\section{Introduction}
The formation of N-substituted imines (Schiff base) was described by Hugo Schiff in 1864 \unskip~\citep{769253:18295762}. Schiff bases have interesting applications such as promising biological activity and industrial fields \unskip~\citep{769253:18295356}. Complexion Schiff bases with metals formed mono-, di- and poly-nuclear metal completes. They behaved as monodentate, bidentate, or tridentate ligands depending on the number of electrons donating group \unskip~\citep{769253:18295354}. Schiff bases have interesting biological and pharmacological activities such as antimicrobial, antidepressant, anti-HIV, cytotoxicity, analgesic, antileishmanial, anticonvulsant, insecticides, fungicides, anticancer, tuberculostatic, and anti-inflammatory \unskip~\citep{769253:18295763}. In addition, Schiff bases showed antibacterial and antiviral activities \unskip~\citep{769253:18295815}. 


\begin{table*}[!htbp]
\caption{\boldmath {Three Schiff base compounds and physicalproperties. } }
\label{tw-6ef676b0815e}
\centering 
\begin{threeparttable}

\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.20\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor}Compound No. & Molecular formula & Yield (\%) & Color & M.P. (\ensuremath{^{0}}C)\\
\tblmidrule 
A1 &
  C14H12NOCl &
  82 &
  Pale &
  126\\
A2 &
  C14H12NOBr &
  75 &
  Grey &
  148\\
A3 &
  C14H13NO2 &
  87 &
  Dark green &
  205\\
\tblbottomrule 
\end{tabulary}\par 
\begin{tablenotes}\footnotesize 
    
\item{ M.P.: Melting point }
\end{tablenotes}
\end{threeparttable}

\end{table*}

\begin{table*}[!htbp]
\caption{\boldmath {Three Schiff bases compounds; FT.IR data } }
\label{tw-d74798838bf6}
\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.19980000000000004\linewidth-2\tabcolsep}p{\dimexpr.2002\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor} & \ensuremath{\upsilon } (C-H)Str. Aromatic \mbox{}\protect\newline Aliphatic \mbox{}\protect\newline cm\ensuremath{^{-1}} & \ensuremath{\upsilon } (C=N) \mbox{}\protect\newline Str. Imin cm\ensuremath{^{-1}} \mbox{}\protect\newline  & \ensuremath{\upsilon }(C-H) \mbox{}\protect\newline Ben. Aromatic \mbox{}\protect\newline cm\ensuremath{^{-1}} & Other cm\ensuremath{^{-1}}\\
\tblmidrule 
A1 &
  2962 \mbox{}\protect\newline 2881 &
  1620 &
  839 &
  \ensuremath{\upsilon }(Ar-Cl)Str.  Ben:1255\\
A2 &
  2958 \mbox{}\protect\newline 2879 &
  1622 &
  839 &
  \ensuremath{\upsilon }(Ar-Br)Str. \mbox{}\protect\newline 1249\\
A3 &
  2916 \mbox{}\protect\newline 2839 &
  1606 &
  842 &
  \ensuremath{\upsilon }(Ar-Br)Str. \mbox{}\protect\newline 3431\\
\tblbottomrule 
\end{tabulary}\par 
\end{table*}

\begin{table*}[!htbp]
\caption{\boldmath {Diameters of inhibitions zones of all derivative compounds against gram negative and positive bacteria. } }
\label{tw-8e6ee7ae6665}
\centering 
\begin{threeparttable}

\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.27800000000000004\linewidth-2\tabcolsep}p{\dimexpr.18959999999999997\linewidth-2\tabcolsep}p{\dimexpr.1942\linewidth-2\tabcolsep}p{\dimexpr.1382\linewidth-2\tabcolsep}p{\dimexpr.20\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor}{\multirow{3}{*}{Derivative compound }} & \multicolumn{4}{p{\dimexpr(.7219999999999999\linewidth-2\tabcolsep)}}{Pathogenic bacteria }\\
\rowcolor{kwdboxcolor} & \multicolumn{2}{p{\dimexpr(.38379999999999995\linewidth-2\tabcolsep)}}{Pseudomonas aeruginosa} & \multicolumn{2}{p{\dimexpr(.3382\linewidth-2\tabcolsep)}}{Staphylococcus aureus}\\
\rowcolor{kwdboxcolor} & Con.  & M\ensuremath{\pm}S & Con.  & M\ensuremath{\pm}S\\
\tblmidrule 
\multicolumn{1}{p{\dimexpr(.27800000000000004\linewidth-2\tabcolsep)}}{\multirow{2}{\linewidth}{A1 \mbox{}\protect\newline }} &
  100 &
  7.8333 \ensuremath{\pm} 0.44096  &
  100 &
  7.8000 \ensuremath{\pm} 0.47258 \\
 &
  200 &
  8.1167 \ensuremath{\pm} 0.49694  &
  200 &
  8.0000 \ensuremath{\pm} 0.57735 \\
\multicolumn{1}{p{\dimexpr(.27800000000000004\linewidth-2\tabcolsep)}}{\multirow{2}{\linewidth}{A2 \mbox{}\protect\newline }} &
  100 &
  8.3667 \ensuremath{\pm} 0.59255  &
  100 &
  8.6667 \ensuremath{\pm} 0.72648\\
 &
  200 &
  10.000 \ensuremath{\pm} 0.28868  &
  200 &
  9.5000 \ensuremath{\pm} 0.76376 \\
\multicolumn{1}{p{\dimexpr(.27800000000000004\linewidth-2\tabcolsep)}}{\multirow{2}{\linewidth}{A3}} &
  100 &
  13.333 \ensuremath{\pm} 0.72648 &
  100 &
  13.167 \ensuremath{\pm} 0.44096 \\
 &
  200 &
  18.417 \ensuremath{\pm} 0.54645  &
  200 &
  16.000 \ensuremath{\pm} 0.57735 \\
\tblbottomrule 
\end{tabulary}\par 
\begin{tablenotes}\footnotesize 
    
\item{Con.; Concentration mg/ml. M\ensuremath{\pm}S; Mean\ensuremath{\pm}standard error}
\end{tablenotes}
\end{threeparttable}

\end{table*}

    
\section{Materials and Methods}
\textbf{Chemicals}

In this study, all chemicals were provided by the Merck, BDH, and Fluke Chemicals Company.

\textbf{Instruments}

- Electrothermal melting point apparatus (UK) was used to record the melting point.

- FTIR instrument SHIMADZU FTIR-8400S spectrophotometer was used to detect FTIR spectra by using KBr disc. 


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\centering \makeatletter\IfFileExists{images/25df992f-9078-41b5-a9dd-d14e706d1a17-upicture1.png}{\includegraphics{images/25df992f-9078-41b5-a9dd-d14e706d1a17-upicture1.png}}{}
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\caption{\boldmath {Structure formula of three synthesized compounds}}
\label{f-1917409731c7}
\end{figure*}
\egroup

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\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/d31efaf2-33f7-4216-a281-7adff206bb32-upicture2.png}{\includegraphics{images/d31efaf2-33f7-4216-a281-7adff206bb32-upicture2.png}}{}
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\caption{\boldmath {A1 compound; the FT.IR spectrum }}
\label{f-f3a3e749bf1e}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/e9c66ba7-3ee5-45b1-8a09-9b73e19a9e1e-upicture3.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/e9c66ba7-3ee5-45b1-8a09-9b73e19a9e1e-upicture3.png}{\includegraphics{images/e9c66ba7-3ee5-45b1-8a09-9b73e19a9e1e-upicture3.png}}{}
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\caption{\boldmath {A2 compound; the FT.IR spectrum }}
\label{f-8a35b38a9a7d}
\end{figure*}
\egroup

\bgroup
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\centering \makeatletter\IfFileExists{images/ced87f88-3360-4772-8a70-4cb32317b878-upicture4.png}{\includegraphics{images/ced87f88-3360-4772-8a70-4cb32317b878-upicture4.png}}{}
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\caption{\boldmath {A3 compound; the FT.IR spectrum }}
\label{f-b36af580c9c6}
\end{figure*}
\egroup

\bgroup
\fixFloatSize{images/5210d2e9-085a-460c-b9f4-59de58a490a5-upicture5.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/5210d2e9-085a-460c-b9f4-59de58a490a5-upicture5.png}{\includegraphics{images/5210d2e9-085a-460c-b9f4-59de58a490a5-upicture5.png}}{}
\makeatother 
\caption{\boldmath {Effect of three derivative compounds with concentration 200 mg/ml against gram negative bacteria.}}
\label{f-fca61145ae4b}
\end{figure*}
\egroup
\textbf{ Schiff bases derivatives [A\ensuremath{_{1}} {\textendash} A\ensuremath{_{3}}] synthesis}

\textbf{The general method}

\unskip~\citep{769253:18295996} method was used in this study as follows: Glacial acetic acid (2 drops) was added to the mixture of 4-methoxyaniline (0.01 mole) and a variety of substituted benzaldehyde in 40 ml absolute ethanol. The mixture was refluxed for 2 to 4 hours, then the volatiles were evaporated, and the residue was poured into water. By filtration, all precipitate was collected and washed with water. The three compounds were named A1, A2, and A3. All steps are shown in Table~\ref{tw-6ef676b0815e} and the structural formula of the three compounds are shown in Figure~\ref{f-1917409731c7}. 

\textbf{Gram-negative and gram-positive bacterial isolates }

 Two bacterial isolates were selected in this study: P.aeruginosa  (gram-negative bacteria) and S.aureus (gram-positive bacteria) were obtained from the University of Kufa, Faculty of Science, Department of Microbiology, and were isolated from the patients with wound infection. All bacteria isolates were identified according to the slandered bacteriological methods \unskip~\citep{769253:18295353}.

\textbf{Antibacterial activity test }

 Agar well diffusion method \unskip~\citep{769253:18295357} was used in this study as follows: the three derivative compounds (A1, A2, and A3) with concentrations (100 mg/ml, 200 mg/ml) for each compound were prepared and dissolved with DMSO \unskip~\citep{769253:18295910}. By sterile swab, all Mueller-Hinton agar plated were streaked with 1.5 x 10\ensuremath{^{5 }}P.aeruginosa  and S.aureus alone \unskip~\citep{769253:18295919}. Three wells were made in all streaked Mueller-Hinton agar plates with diameters of 5 mm by using cork-borer. Fifty microliters of each derivative compounds were transferred to each well and incubated at 37 \ensuremath{^\circ}C for 24 hours. All inhibition zones were measured in millimeters \unskip~\citep{769253:18295961}.  

\textbf{Statistical Analysis }

The tenth version of GraphPad Prism Windows software was used to compare the diameters of inhibition zones using mean \ensuremath{\pm} standard error \unskip~\citep{769253:18295352}.
    
\section{Results and Discussion}
Schiff base compounds [A\ensuremath{_{1}} {\textendash} A\ensuremath{_{3}}] were synthesized by the reaction of 4-methoxyaniline with different aromatic benzaldehyde. All absorption bands (3471 cm\ensuremath{^{-1}}) and (3379 cm\ensuremath{^{-1}}) corresponding to the asymmetric and symmetric stretching vibration of {\textendash}NH\ensuremath{_{2}} group in 4-methoxyaniline disappeared. Also, the absorption band (1680 {\textendash} 1720 cm\ensuremath{^{-1}}) corresponding to the (C=O) disappeared \unskip~\citep{769253:18295992}. The FTIR showed that the absorption band (1606 {\textendash} 1622 cm-1) corresponding to the imine group (C=N) appeared \unskip~\citep{769253:18295355}. Table~\ref{tw-d74798838bf6} and Figures~\ref{f-f3a3e749bf1e}, \ref{f-8a35b38a9a7d} and~\ref{f-b36af580c9c6} show the other functional groups. 

\textbf{Results of antibacterial activity }

Figure~\ref{f-fca61145ae4b} and Table~\ref{tw-8e6ee7ae6665} showed that all three derivative compounds had good antibacterial activity against the two types of pathogenic bacteria. But the derivative compound A3 with a concentration of 200 mg/ml had a good antibacterial effect against the gram-negative and gram-positive bacteria with a diameter of inhibition zone of 18.417 \ensuremath{\pm} 0.54645 and 16.000 \ensuremath{\pm} 0.57735, respectively.
    
\section{Conclusions}
The three compounds in this study have good antibacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus. Therefore, they can be considered as good raw materials to synthesize a new ointment for the treatment of bacterial infection. 
\section*{Acknowledgements}We offer special thanks to the University of Kufa, Faculty of Science, Department of Microbiology, for providing wound infection isolates from patients. 

\textbf{Funding Support}

There was no funding in this work. Authors themselves funded it. 

\textbf{Conflict Of Interest}

There was no conflict of interest in this work. 
    

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