Heteroatom macrocyclic ligands antifungal and antimicrobial properties of some of synthesis and investigation

Yüksek Lisans Tezi2,6-piridindikarboksilik asitten başlayarak altı yeni makro-heterosiklik amit sentezlenmiştir. Bu amaçla 2,6-piridindikarboksilik asit önce esterleştirilmiş, ardından diester NaBH4 ile indirgenerek alkole dönüştürülmüş, alkol p-TsCl yardımıyla tosilata dönüştürüldükten sonra bu ditosilat bazik ortamda 2-aminotiyofenol ile reaksiyona sokulmuştur. Ele geçen molekül altı farklı diasit klorür ile kloroform içinde reaksiyona sokularak seyreltik ortamda halka kapanması sağlanmıştır. Daha sonra elde edilen bileşikler kolon kromotografisi ile saflaştırılmış, IR, NMR ve kütle spektroskopisi yardımıyla yapıları açıklanmıştır.Son olarakta antibakteriyel ve antifungal aktiviteleri belirlenmiştir.Anahtar Kelimeler:Antifungal; Makro-heterosiklik amit.AbstractStarting from 2,6-pyridinedicarboxylic acid, six new macro-heterocylic amides were synthesized. As a first step, 2,6 pyridinedinedicarboxylic acid was esterified, then reduced with NaBH4 to obtain corresponding alcohol. Next, the alcohol was converted to its tosylate by using TsCl and followed by reaction with 2-aminothiophenol in basic media. Resulting aromatic diamine were treated with six different diacid dichlorides in a very dilute solution of cloroform to afford the cyclization products. Finally compounds were chromotographed and their structues were proven by using IR, NMR and mass spectroscopy. At last antibacterial and antifungal activities of these compounds were investigated.Keywords : Antifungal; Macro-heterocylic amide

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

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