Synthesis and comparative study on the antibacterial activity organotin(IV) 3-hydroxybenzoate compounds

Abstract

The synthesis and comparative study on the antibacterial activity of three organotin(IV) compounds, namely dibutyltin(IV) bis-(3-hydroxybenzoate), [Bu2Sn(3-HBz)2] (7), diphenyltin(IV) bis-(3-hydroxybenzoate), [Ph2Sn(3-HBz)2] (8), and triphenyltin(IV) 3-hydroxybenzoate, [Ph3Sn(3-HBz)] (9) which were prepared by the reaction of dibutyltin(IV) oxide, [Bu2SnO] (4), diphenyltin(IV) dihydroxide, [Ph2Sn(OH)2] (5), and triphenyltin(IV) hydroxide, [Ph3SnOH] (6) with 3-hydroxybenzoic acid (3-HBz) has successfully been performed. The characterization of these compounds were done using 1H and 13C NMR, IR, UV spectroscopies and their compositions were determined based on microanalytical data. Antibacterial activity of these compounds was demonstrated at concentrations of 1.89 × 10−4, 1.81 × 10−4, and 1.72 × 10−4 M, respectively by dilution method against Pseudomonas aeruginosa. Similarly, the compounds were active at concentration of 1.87 × 10−4, 1.79 × 10−4, and 1.71 × 10−4 M, respectively, against Bacillus subtilis. These activities are comparable to that of streptomycin at a concentration of 1.70 × 10−4 M as a positive control, but the halozone of compounds 7, 8, and 9 were slightly lower than that of streptomycin’s halozone. The results obtained suggest that the compounds synthesized have potential as antibacterial agents.

Synthesis, Characterization, and Comparison of Disinfectant Bioactivity Test of Two Triphenyltin(IV) Compounds

“…The synthesis of organotin(IV) compound Two organotin(IV) compounds, [Ph3Sn(4-HABz)] (2) and Ph3Sn(4-HNBz)] compounds were obtained as yellow and white solid, respectively have been successfully synthesized from the reaction of compound 1 with 4-HABz and 4-HNBz based on the procedures described in the literature (14,15,20,22,(24)(25)(26)(27)(28). The schematic reaction for the synthesis of compounds 2 and 3 are shown in Figure 1, the products of the synthesis for compounds 2 and 3 were 84.09% and 80.70%, respectively.…”

“…Two target compounds of triphenyltin(IV) 4aminobenzoate (2) and triphenyltin(IV) 4nitrobenzoate (3) were prepared by the reaction between the starting compound triphenyltin(IV) hydroxide (1) with 4-HABz and 4-HNBz using the published method (14,15,20,22,(24)(25)(26)(27)(28). The following procedure was performed:…”

“…The NMR data of the compounds synthesized were carefully analyzed to ascertain the successful in the synthesis of compounds 2 and 3. The typical chemical shifts for compounds 2 and 3 prepared were characterized carefully and compared to the data available in the literature (14,15,20,22,(24)(25)(26)(27)(28). Based on the data of 1 H NMR spectrum for compound 2, the chemical shifts of phenyl protons attached to tin metal appeared as expected in the range of 7.440 for H2 and H6 to 7.460 ppm for H3 and H5, while the protons in benzoate ring appeared at 7.744-7.843 ppm.…”

“…The current results from the study on organotin(IV) compounds have revealed that some organotin(IV) carboxylates show promising activities in many biological tests. For example, they have been widely used in the biological activities as antifungal (3,(7)(8)(9), antioxidant activities (10,11), antimalarial and antiplasmodial agents (12)(13)(14)(15), antiviral agents (16,17), antitumor and anticancer (18)(19)(20), corrosion inhibitor (21)(22)(23) and antibacterial (24)(25)(26)(27)(28)(29)(30). Moreover, these compounds have been found to exhibit strong activity as disinfectant (31).…”

Sintesis, Karakterisasi, dan Uji Aktivitas Antibakteri Senyawa Organotimah(IV) 4-Nitrobenzoat

“…Alternatif lain guna memperoleh senyawa yang efektif sebagai antibiotik adalah dikembangkannya senyawa baru dan diuji aktivitasnya (Hadi et al, 2021a;Mantravadi et al, 2019;Samsuar et al, 2021). Senyawa turunan organotimah telah dilaporkan memiliki berbagai aktivitas biologis yang sangat menarik sebagai antikanker dan antitumor (Hadi et al, 2012;Rehman et al, 2009;Sirajuddin et al, 2021;Uddin et al, 2021), antimalaria (Hadi et al, 2018b;Hadi et al, 2021b;Hansch and Verma, 2009), penghambat korosi (Hazani et al, 2019;Singh et al, 2010), dan antifungi (Rocha et al, 2016), juga diketahui memiliki aktivitas yang sangat baik dalam menghambat (membunuh) pertumbuhan bakteri (Annissa et al, 2017;Baul, 2008;Hadi et al, 2018a;Hadi et al, 2021a;Mantravadi et al, 2019;Samsuar et al, 2021). Kekuatan aktivitas senyawa organotimah terhadap bakteri, tidak…”