Synthesis, structural aspects, antimicrobial activity and ion transportation investigation of four new [2+2] condensed 24-membered cycloheterphane peptides

Dulger, Basaran/0000-0002-3184-2652; Zaim, Omer/0000-0002-3472-5611; Dulger, Basaran/0000-0002-3184-2652WOS: 000339274100016Four novel [2 + 2] condensed tetramide-tetrathioether cycloheterophane (L (1) -L (4) ), possessing thioether as ligating units have been prepared. The compounds were characterized by elemental analyses, mass, FT-IR, H-1, and C-13 NMR spectral data. The 24-membered macrocycles have well organized symmetrical structures lacking any configurational isomerism. Ion transportation was carried out with macrocycle L (1) and L (4) against Na+, K+ and Ag+ cations. It showed a high propensity of binding with soft Ag+ cation that it undergoes configurational change during complexation. This phenomenon is not observed with hard cations, but K+ ion passes through the cavity while Na+ ions are retained. The antimicrobial activities of the compounds were evaluated using the disk diffusion method in dimethyl sulfoxide as well as the minimal inhibitory concentration dilution method, against several bacteria and yeast cultures. The results were compared with those of commercial antibiotic and antifungal agents. Structure activity relationships were also discussed.Fatih University Scientific Research CentreFatih University [P50021202_Y(2363)]; Trakya UniversityTrakya University [TUBAP-2010/174]We would like to extend our gratitude to the Fatih University Scientific Research Centre (Project-P50021202_Y(2363) and the Trakya University (Grant # TUBAP-2010/174) for their financial support. Dr. Ahmet Ceyhan Goren and Gokhan Bilsel (TUBITAK-UME), is acknowledged for the Mass analysis

FT-Raman, FT-IR and NMR spectra, vibrational assignments and density functional studies of 1,3-bis(benzimidazol-2-yl)-2-thiapropane ligand and its Zn(II) halide complexes’

1,3-bis(benzimidazol-2-yl)-2-thiapropane (L) ligand and its zinc halide ZnX2 (X = Cl, Br, I) complexes have been synthesized. The compounds were characterized using the elemental analysis, molar conductivity, FT-Raman, FT-IR (mid i.r., far i.r.), H-1 and C-13 NMR spectra, and quantum chemical calculations performed with Gaussian 03 package program set. The optimized geometries and vibrational frequencies of the ligand and [Zn(L)Cl-2] complex were calculated using the DFT/ B3LYP method with a 6-31g(d) basis set. The geometry optimization of [Zn(L)Cl-2] yields a slightly distorted tetrahedral environment around Zn ion, while the molecule clearly reveals the Cs symmetry. The molar conductivity data reveals that the complexes are neutral. The ligand is bidentate, via two of the imine nitrogen atoms in the bis-imidazole ring units, and together with the monodentate coordination of the two halides to the metal centre

FT-Raman, FT-IR and NMR spectra, vibrational assignments and density functional studies of 1,3-bis(benzimidazol-2-yl)-2-thiapropane ligand and its Zn(II) halide complexes

1,3-bis(benzimidazol-2-yl)-2-thiapropane (L) ligand and its zinc halide ZnX2 (X = Cl, Br, I) complexes have been synthesized. The compounds were characterized using the elemental analysis, molar conductivity, FT-Raman, FT-IR (mid i.r., far i.r.), H-1 and C-13 NMR spectra, and quantum chemical calculations performed with Gaussian 03 package program set. The optimized geometries and vibrational frequencies of the ligand and [Zn(L)Cl-2] complex were calculated using the DFT/ B3LYP method with a 6-31g(d) basis set. The geometry optimization of [Zn(L)Cl-2] yields a slightly distorted tetrahedral environment around Zn ion, while the molecule clearly reveals the Cs symmetry. The molar conductivity data reveals that the complexes are neutral. The ligand is bidentate, via two of the imine nitrogen atoms in the bis-imidazole ring units, and together with the monodentate coordination of the two halides to the metal centre

Synthesis, structural aspects, antimicrobial activity and ion transport investigation of five new [1+1] condensed cycloheterophane peptides

Zaim, Omer/0000-0002-3472-5611; Dulger, Basaran/0000-0002-3184-2652; Dulger, Basaran/0000-0002-3184-2652; Gurbuz, Mustafa Ulvi/0000-0002-8684-5746WOS: 000334496700015Five novel [1+1] condensed cycloheterophane peptides were synthesized via reaction of pyridine-2,6-bis(2-aminothiophenoxymethyl) with several diacid chlorides: glutaryl dichloride, adipoyl dichloride, 2,2'-thiodiacetyl chloride, dithiodiglycoloyl chloride and 3,3'-thiodipropionoyl chloride combinations (L-1-L-5). The compounds were characterized by elemental analyses, mass, FT-IR, H-1, and C-13 NMR spectral data. The antimicrobial activities of the compounds were evaluated using the disk diffusion method in dimethyl sulfoxide as well as the minimal inhibitory concentration dilution method, against several bacteria and yeast cultures. The results were compared with those of commercial antibiotic and antifungal agents. Structure activity relationships were also discussed. Permeability of compound L-5 against Na+ and K+ were also investigated.Fatih University Scientific Research CentreFatih University [P50021004_G1452]; Trakya UniversityTrakya University [TUBAP-2010/174]We would like to extend our gratitude to the Fatih University Scientific Research Centre ( Project-P50021004_G1452) and the Trakya University (Grant # TUBAP-2010/174) for their financial support. Dr. Ahmet Ceyhan Goren and Gokhan Bilsel (TUBITAK-UME), is acknowledged for the Mass analysis