Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity

In this study, four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS and HRMS techniques and single c...

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Veröffentlicht in:Inorganica Chimica Acta 2017-07, Vol.463, p.88-96
Hauptverfasser: Gemili, Muge, Sari, Hayati, Ulger, Mahmut, Sahin, Ertan, Nural, Yahya
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description In this study, four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS and HRMS techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Acid dissociation constants of the ligands and stability constants of their Pt(II) and Ni(II) complexes were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program. Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains, and their antimycobacterial activity was investigated against the M. tuberculosis H37Rv strain. [Display omitted] •Synthesis of four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives.•Acid dissociation constants study of the ligands.•Stability constants study of the Pt(II) and Ni(II) complexes.•Anti(myco)bacterial activity studies for the ligands and their Pt(II) and Ni(II) complexes.•X-ray study for the ligand, Pt(II) and Ni(II) complexes. In this study, four novel Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS, HRMS and elemental analysis techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, with space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Furthermore, the ligands behave as bidentate and bind to the metal atom via the S and O atoms. Acid dissociation constants of the ligands were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydro
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The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Acid dissociation constants of the ligands and stability constants of their Pt(II) and Ni(II) complexes were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program. Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains, and their antimycobacterial activity was investigated against the M. tuberculosis H37Rv strain. [Display omitted] •Synthesis of four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives.•Acid dissociation constants study of the ligands.•Stability constants study of the Pt(II) and Ni(II) complexes.•Anti(myco)bacterial activity studies for the ligands and their Pt(II) and Ni(II) complexes.•X-ray study for the ligand, Pt(II) and Ni(II) complexes. In this study, four novel Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS, HRMS and elemental analysis techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, with space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Furthermore, the ligands behave as bidentate and bind to the metal atom via the S and O atoms. Acid dissociation constants of the ligands were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program and at least three acid dissociation constants were determined for each ligand. Stability constants of Pt(II) and Ni(II) complexes of the ligands were determined by potentiometric titration under the same conditions as stated above. Determination of the stability constant studies show that the ligands tend to form with Pt(II) ion in acidic medium as 1:1 (M:L) and in basic medium as 1:2 (M:L), but the ligands tend to form with Ni(II) ion in both acidic medium and basic medium as 1:2 (M:L). Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains. The ligands and their Pt(II) and Ni(II) complexes exhibited antibacterial activity against mentioned bacterial strains in the range of 62.5–125μg/mL, 62.5–250μg/mL and 62.5–125μg/mL, respectively. Antimycobacterial activity of the compounds was investigated against the M. tuberculosis H37Rv strain. The compounds exhibit antimycobacterial activity in the range of 40–80μg/mL.</description><identifier>ISSN: 0020-1693</identifier><identifier>EISSN: 1873-3255</identifier><identifier>DOI: 10.1016/j.ica.2017.04.026</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Acetonitrile ; Acid dissociation constant ; Biological activity ; Chemical compounds ; Chemical synthesis ; Complex ; Coordination compounds ; Derivatives ; E coli ; Infrared radiation ; Ligands ; Nickel ; NMR ; Nuclear magnetic resonance ; Physical properties ; Planar structures ; Platinum ; Pyrrolidine ; Single crystals ; Sodium chloride ; Stability ; Stability constant ; Stability constants ; Structural analysis ; Thiourea ; Titration ; Tuberculosis ; X-ray diffraction</subject><ispartof>Inorganica Chimica Acta, 2017-07, Vol.463, p.88-96</ispartof><rights>2017 Elsevier B.V.</rights><rights>Copyright Elsevier Science Ltd. Jul 1, 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-fcd252cbd98d22d84a4adae9aa3e05b5ef3a3281d568de68b368064e64031d743</citedby><cites>FETCH-LOGICAL-c325t-fcd252cbd98d22d84a4adae9aa3e05b5ef3a3281d568de68b368064e64031d743</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ica.2017.04.026$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids></links><search><creatorcontrib>Gemili, Muge</creatorcontrib><creatorcontrib>Sari, Hayati</creatorcontrib><creatorcontrib>Ulger, Mahmut</creatorcontrib><creatorcontrib>Sahin, Ertan</creatorcontrib><creatorcontrib>Nural, Yahya</creatorcontrib><title>Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity</title><title>Inorganica Chimica Acta</title><description>In this study, four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS and HRMS techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Acid dissociation constants of the ligands and stability constants of their Pt(II) and Ni(II) complexes were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program. Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains, and their antimycobacterial activity was investigated against the M. tuberculosis H37Rv strain. [Display omitted] •Synthesis of four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives.•Acid dissociation constants study of the ligands.•Stability constants study of the Pt(II) and Ni(II) complexes.•Anti(myco)bacterial activity studies for the ligands and their Pt(II) and Ni(II) complexes.•X-ray study for the ligand, Pt(II) and Ni(II) complexes. In this study, four novel Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS, HRMS and elemental analysis techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, with space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Furthermore, the ligands behave as bidentate and bind to the metal atom via the S and O atoms. Acid dissociation constants of the ligands were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program and at least three acid dissociation constants were determined for each ligand. Stability constants of Pt(II) and Ni(II) complexes of the ligands were determined by potentiometric titration under the same conditions as stated above. Determination of the stability constant studies show that the ligands tend to form with Pt(II) ion in acidic medium as 1:1 (M:L) and in basic medium as 1:2 (M:L), but the ligands tend to form with Ni(II) ion in both acidic medium and basic medium as 1:2 (M:L). Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains. The ligands and their Pt(II) and Ni(II) complexes exhibited antibacterial activity against mentioned bacterial strains in the range of 62.5–125μg/mL, 62.5–250μg/mL and 62.5–125μg/mL, respectively. Antimycobacterial activity of the compounds was investigated against the M. tuberculosis H37Rv strain. The compounds exhibit antimycobacterial activity in the range of 40–80μg/mL.</description><subject>Acetonitrile</subject><subject>Acid dissociation constant</subject><subject>Biological activity</subject><subject>Chemical compounds</subject><subject>Chemical synthesis</subject><subject>Complex</subject><subject>Coordination compounds</subject><subject>Derivatives</subject><subject>E coli</subject><subject>Infrared radiation</subject><subject>Ligands</subject><subject>Nickel</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Physical properties</subject><subject>Planar structures</subject><subject>Platinum</subject><subject>Pyrrolidine</subject><subject>Single crystals</subject><subject>Sodium chloride</subject><subject>Stability</subject><subject>Stability constant</subject><subject>Stability constants</subject><subject>Structural analysis</subject><subject>Thiourea</subject><subject>Titration</subject><subject>Tuberculosis</subject><subject>X-ray diffraction</subject><issn>0020-1693</issn><issn>1873-3255</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kc9q3DAQxkVpodukD5CbIJcU1o7-WWunpxDSdiEkgbanEoQsjWMtXsuRlKXO-_Q9q-z23JNG_Oab-YYPoRNKSkqoPN-UzuiSEboqiSgJk2_QgtYrXnBWVW_RghBGCiob_h59iHFDCCeSVwv05z6drdefsB4tvnX70vjtNMBviNh32Juk-9kGP80h-MH_4ktRmIfDD_Bt0cL44uch9c4_B9DYQnA7ndwO4gX-Po-ph-jiEpteB21Spi-Z-nGJp36O2fSAp0y2kFHc22hd3vO4J1ngdi7Nx-hdp4cIH_-9R-jnl-sfV9-Km7uv66vLm8LkM1PRGcsqZlrb1JYxWwsttNXQaM2BVG0FHdec1dRWsrYg65bLmkgBUhBO7UrwI3R6mDsF__QMMalNvmrMKxUjopGiqViTu-ihywQfY4BOTcFtdZgVJeo1DbVR2b56TUMRoXIaWfP5oIFsf-cgqGgcjAasC2CSst79R_0XKrmV1Q</recordid><startdate>20170701</startdate><enddate>20170701</enddate><creator>Gemili, Muge</creator><creator>Sari, Hayati</creator><creator>Ulger, Mahmut</creator><creator>Sahin, Ertan</creator><creator>Nural, Yahya</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20170701</creationdate><title>Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity</title><author>Gemili, Muge ; Sari, Hayati ; Ulger, Mahmut ; Sahin, Ertan ; Nural, Yahya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-fcd252cbd98d22d84a4adae9aa3e05b5ef3a3281d568de68b368064e64031d743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acetonitrile</topic><topic>Acid dissociation constant</topic><topic>Biological activity</topic><topic>Chemical compounds</topic><topic>Chemical synthesis</topic><topic>Complex</topic><topic>Coordination compounds</topic><topic>Derivatives</topic><topic>E coli</topic><topic>Infrared radiation</topic><topic>Ligands</topic><topic>Nickel</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Physical properties</topic><topic>Planar structures</topic><topic>Platinum</topic><topic>Pyrrolidine</topic><topic>Single crystals</topic><topic>Sodium chloride</topic><topic>Stability</topic><topic>Stability constant</topic><topic>Stability constants</topic><topic>Structural analysis</topic><topic>Thiourea</topic><topic>Titration</topic><topic>Tuberculosis</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gemili, Muge</creatorcontrib><creatorcontrib>Sari, Hayati</creatorcontrib><creatorcontrib>Ulger, Mahmut</creatorcontrib><creatorcontrib>Sahin, Ertan</creatorcontrib><creatorcontrib>Nural, Yahya</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Inorganica Chimica Acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gemili, Muge</au><au>Sari, Hayati</au><au>Ulger, Mahmut</au><au>Sahin, Ertan</au><au>Nural, Yahya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity</atitle><jtitle>Inorganica Chimica Acta</jtitle><date>2017-07-01</date><risdate>2017</risdate><volume>463</volume><spage>88</spage><epage>96</epage><pages>88-96</pages><issn>0020-1693</issn><eissn>1873-3255</eissn><abstract>In this study, four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS and HRMS techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Acid dissociation constants of the ligands and stability constants of their Pt(II) and Ni(II) complexes were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program. Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains, and their antimycobacterial activity was investigated against the M. tuberculosis H37Rv strain. [Display omitted] •Synthesis of four novel Pt(II) and Ni(II) complexes of the octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives.•Acid dissociation constants study of the ligands.•Stability constants study of the Pt(II) and Ni(II) complexes.•Anti(myco)bacterial activity studies for the ligands and their Pt(II) and Ni(II) complexes.•X-ray study for the ligand, Pt(II) and Ni(II) complexes. In this study, four novel Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS, HRMS and elemental analysis techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, with space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni(II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Furthermore, the ligands behave as bidentate and bind to the metal atom via the S and O atoms. Acid dissociation constants of the ligands were determined by potentiometric titration method in 25% (v/v) acetonitrile-water hydroorganic solvent at 25±0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD computer program and at least three acid dissociation constants were determined for each ligand. Stability constants of Pt(II) and Ni(II) complexes of the ligands were determined by potentiometric titration under the same conditions as stated above. Determination of the stability constant studies show that the ligands tend to form with Pt(II) ion in acidic medium as 1:1 (M:L) and in basic medium as 1:2 (M:L), but the ligands tend to form with Ni(II) ion in both acidic medium and basic medium as 1:2 (M:L). Antibacterial activity of the ligands and their complexes was investigated against S. aureus, B. subtilis, A. hydrophila, E. coli and A. baumannii standard bacterial strains. The ligands and their Pt(II) and Ni(II) complexes exhibited antibacterial activity against mentioned bacterial strains in the range of 62.5–125μg/mL, 62.5–250μg/mL and 62.5–125μg/mL, respectively. Antimycobacterial activity of the compounds was investigated against the M. tuberculosis H37Rv strain. The compounds exhibit antimycobacterial activity in the range of 40–80μg/mL.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.ica.2017.04.026</doi><tpages>9</tpages></addata></record>
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subjects Acetonitrile
Acid dissociation constant
Biological activity
Chemical compounds
Chemical synthesis
Complex
Coordination compounds
Derivatives
E coli
Infrared radiation
Ligands
Nickel
NMR
Nuclear magnetic resonance
Physical properties
Planar structures
Platinum
Pyrrolidine
Single crystals
Sodium chloride
Stability
Stability constant
Stability constants
Structural analysis
Thiourea
Titration
Tuberculosis
X-ray diffraction
title Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity
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