Serkan Yavuz

The synthesis and investigation of the antimicrobial activity of some new phenylselanyl-1-(toluene-4-sulfonyl)-1H-tetrazole derivatives

The sulfonamide functional group has aroused interest in both medicinal and bioorganic chemistry. In this study, some new phenylselanyl–1–(toluene-4-sulfonyl)-1H-tetrazole derivatives (2a–f) have been synthesized using dicyclohexylcarbodiimide/dimethylaminopyridine (DCC/DMAP). The structures of the presently synthesized compounds were elucidated by spectroscopic methods [Fourier-transform infrared (FTIR) spectroscopy, 1H nuclear magnetic resonance (NMR), 13C nuclear magnetic resonance-attached proton test (13C NMR-APT), and mass spectrometry (MS)]. In addition, the antimicrobial activity of the synthesized compounds and two antibiotics [sulfamethoxazole (SMX) and sulfamerazine (SRZ)] were investigated against some microorganisms.Graphical AbstractThe synthesis and investigation of the antimicrobial activity of some new phenylselanyl-1-(toluene-4-sulfonyl)-1H-tetrazole derivativesYılmaz Yıldırır, M. Faruk Us, Naki Çolak, Hamdi Özkan, Serkan Yavuz, Ali Disli, Sahlan Ozturk, Lemi TurkerIn this study, some new phenylselanyl–1–(toluene-4-sulfonyl)-1H- tetrazole derivatives, 2a–f, have been synthesized using DCC/DMAP. In addition to, antimicrobial activity of synthesized compounds and two antibiotics (SMX, SRZ) were investigated against some microorganisms. Reagents and conditions: (i) HCI, (ii) EtONO, -5 – 0°C; (iii) KSeCN, (iv) NaN3, Et3NH+ CI−, Toluene. 2a. R1:H, R2:Cl 2b. 2a. R1:H, R2:CH32c. R1:Cl, R2:H 2d. R1:Br, R2:H 2e. R1:I, R2:H 2f. R1:CH3, R2:H

Ferrocene Derivatives Carrying Urea, Thiourea, and Sulfonamide Moieties: Synthesis and Evaluation of Antibacterial and Antifungal Activities

In the present study, some novel ferrocene derivatives carrying urea, thiourea, and sulfonamide groups were synthesized, and all compounds were characterized by spectral and elemental analyses. These compounds were screened for their antibacterial activities and also their minimum inhibitory concentration (MIC) against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and Gram-negative bacteria (Klebsiella pneumonia and Escherichia coli) and antifungal activities against Saccharomyces cerevisiae and Candida albicans. Amongst the tested compounds, 4b, 4c, 5b, and 6b displayed excellent antimicrobial activity.

Synthesis and Pharmacological Evaluation of Some Novel Thebaine Derivatives: N-(Tetrazol-1H-5-yl)-6,14-endoethenotetrahydrothebaine Incorporating the 1,3,4-Oxadiazole or the 1,3,4-Thiadiazole Moiety

In this study, we synthesized some novel N‐(tetrazol‐1H‐5‐yl)‐6,14‐endoethenotetrahydrothebaine 7α‐substituted 1,3,4‐oxadiazole and 1,3,4‐thiadiazole derivatives as potential analgesic agents. The structures of the compounds were established on the basis of their IR, 1H NMR, 13C NMR, 2D NMR, and high‐resolution mass spectral data. The analgesic activity was evaluated by a rat‐hot plate test model and a rat tail‐flick model. Compound 12 showed analgesic activity higher than that of morphine. In addition to a histopathological and biochemical evaluation, the LD50 dose for the most active compound 12 was determined.

Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles

AbstractIn this study, some substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles have been synthesized (2a–o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 2l).Graphical AbstractIn this study, some substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds, but others are novel). The synthesized compounds were characterized by spectroscopic methods (FTIR, NMR, MS).In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds (except for 2l) have antimicrobial effect against these bacteria. Antimicrobial activities of these compounds were compared with antimicrobial activities of some antibiotics.Scheme 1: Protocol for the synthesis substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles. (a) R1: H, R2: H; (b) R1: F, R2: H; (c) R1: H, R2: F; (d) R1: Cl, R2: H; (e) R1: H, R2: Cl; (f) R1: Br, R2: H; (g) R1: H, R2: Br; (h) R1: I, R2: H; (i) R1: H, R2: I; (j) R1: CH3, R2: H; (k) R1: H, R2: CH3; (l) R1: OCH3, R2: H; (m) R1: H, R2: OCH3; (n) R1: NO2, R2: H; (o) R1: H, R2: NO2.

The Syntheses of Some Novel (Naphthalen-1-yl-selenyl)acetic Acid Derivatives

Some new (naphthalen-1-yl-selenyl)acetic acids derivatives 7a‑d have been synthesized by two different methods, using naphthylselenols or naphthylselenocyanates. The structures of the products were investigated by spectroscopic methods.

Fast method for synthesis of alkyl and aryl-N-methylnitrones.

A simple, fast, efficient and eco-friendly procedure was developed for the synthesis of alkyl and aryl-N-methylnitrones. The corresponding nitrones of aromatic aldehydes, aliphatic aldehydes and alicyclic carbonyl compounds were prepared from N-methylhydroxylamine hydrochloride and Na2CO3-Na2SO4 by simply grinding at room temperature without using solvent.

7α-Methoxy-carbonyl-6,7,8,14-tetra-hydro-6,14-endo-ethenothebaine.

In the molecule of the title compound, C23H27NO5, the furan ring adopts an envelope conformation. Intramolecular C—H⋯O interactions result in the formation of S(5) and S(6) motifs. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules through C(6) and C(8) chains along the [100] and [010] directions, generating a two-dimensional network.

Computer design, synthesis, and bioactivity analyses of drugs like fingolimod used in the treatment of multiple sclerosis

Multiple sclerosis (MS) is a very common disease of vital importance. In the MS treatment, some drugs such as fingolimod which help to protect nerves from damage are used. The main goal of the drug therapy in MS is to take control of the inflammation which leads to the destruction of myelin and axons in nerve cell and thus prevent and stop the progression of the disease. Fingolimod (FTY720) is an orally active immunomodulatory drug that has been used for the treatment of relapsing-remitting multiple sclerosis. It is a sphingosine-1-phosphate receptor modulator which prevents lymphocytes from contributing to an autoimmune reaction by inhibiting egress of lymphocytes them from lymph nodes. In this study, we have computer designed, synthesized and characterized two novel derivatives of FTY720, F1-12h and F2-9, and have determined their underlying mechanism of their beneficial effect in SH-SY5Y, SK-N-SH, and U-118 MG cell lines. For this purpose, we first determined the regulation of the cAMP response element (CRE) activity and cAMP concentration by F1-12h and F2-9 together with FTY720 using pGL4.29 luciferase reporter assay and cAMP immunoassay, respectively. Then, we have determined their effect on MS- and GPCR-related gene expression profiles using custom arrays along with FTY720 treatment at non-toxic doses (EC10). It was found that both derivatives significantly activate CRE and increase cAMP concentration in all three cell lines, indicating that they activate cAMP pathway through cell surface receptors as FTY720 does. Furthermore, F1-12h and F2-9 modulate the expression of the pathway related genes that are important in inflammatory signaling, cAMP signaling pathway, cell migration as well as diverse receptor and transcription factors. Expression of the genes involved in myelination was also increased by the treatment with F1-12h and F2-9. In summary, our data demonstrate that the two novel FTY720 derivatives act as anti-inflammatory ultimately by influencing the gene expression via the cAMP and downstream transcription factor CRE pathway. In conclusion, F1-12h and F2-9 might contribute future therapies for autoimmune diseases such as multiple sclerosis.

Synthesis and Characterization of New Thebaine Derivatives: 2-(6,14-endo-Ethenotetrahydrothebaine-7α;-yl)-5-(N-Arylamino)-1,3,4-Thiadiazoles

Abstract We have synthesized a series of novel 2-(6,14-endo-ethenotetrahydrothebaine-7α-yl)-5-N-arylamino-1,3,4-thiadiazoles (5a–n) as potential narcotic analgesics, which are analogs of morphine. The synthesized compounds exhibit rigid morphine structures, including a 6,14-endo-entheno bridge and a 5-N-arylamino-1,3,4-thiadiazol-2-yl group at C-7 position that adopted S-configuration. The structures and stereochemistry of the compounds were completely assigned using one- and two-dimensional NMR experiments (1H NMR, APT, COSY, NOESY, HMQC, and HMBC), FTIR, and high-resolution mass spectral (HRMS) data. Supplemental materials are available for this article. Go to the publishers online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT

Synthesis and DNA binding of new adenine derivatives incorporating 5-((Alkylthio)-1,3,4-oxadiazol-2-yl)methyl moiety

In this study, a series of new adenine derivatives possessing 1,3,4-oxadiazole moiety with different S-alkyl group were synthesized. The structures of these compounds were established on the basis of FT-IR, 1H, 13C-APT NMR, and HRLC-MS spectral data. Their DNA binding abilities were investigated in vitro by agarose gel electrophoresis. The relationship between the structure and the mentioned biological activities was discussed. The results showed that these compounds 5d and 5c exhibited DNA cleavage activity. Compounds DNA interaction studies reveal that compounds have affinity towards A/A and G/G nucleotides on DNA. None of the compounds at 2500 µM concentration have no inhibitory effect on microbial growth of tested strain of bacteria and yeast strain used in this study.