Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities

In this study, hydroxy benzoin (1-7), benzil (8-14), and benzoin/benzil-O-beta-D-glucosides (15-25) were synthesized to investigate their biological activities. An efficient method for synthesizing hydroxy benzoin compounds (1-7) was prepared from four different benzaldehydes using an ultrasonic bath. Then, antioxidant (FRAP, CUPRAC, and DPPH), antimicrobial (3 Gram (-), 4/6 Gram (+), one tuberculosis and one fungus), and enzyme inhibition (acetylcholinesterase, butyrylcholine esterase, tyrosinase, alpha-amylase, and alpha- glucosidase) for the all synthesized compounds (1-25) were evaluated. And also, four most active compounds (4, 12, 18a+b, and 25) from each group were evaluated to the human cervical cancer cell line (HeLa) and anticancer screening tests against the human retinal normal cell line (RPE). Compound 4 showed HeLa and RPE cancer cell activities as much as cisplatin. The synthesized compounds were characterized by spectroscopic methods (NMR, FT-IR, UV, LC-QTOF-MS) and the ACD NMR program's help

Chemical composition and biological activity of essential oils of sempervivum brevipilum muirhead

This work was supported by grants from Karadeniz Technical University Research Fund.The essential oils of the fresh flower, leaf, and stem of Sempervivum brevipilum Muirhead. (Crassulaceae) were isolated by hydrodistillation in a modified Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of fifty, fourty-three, and thirty-one compounds were identified, constituting over 92.6%, 92.6%, and 94.3% of oil composition of the flower, leaf, and stem of S. brevipilum, respectively. The chemical profile reveals the dominance of hydrocarbons (flower: 65.3%, leaf: 47.6%, stem: 71.1%). The major compounds of essential oils from S. brevipilum were tetracosane (20.2%) in flower, 1,2-diphenyl ethandione (16.1%) in leaf and docosane (30.5%) in stem. Monoterpene hydrocarbons were the major class of terpenoids in flower (2.2%) and in stem (1.8%), oxygenated diterpene was the major class of terpenoids in leaf (4.5%). Oxygenated monoterpenes were in minor amounts in all parts (flower: 0.3%, leaf: 0.7%, stem: 0.1%) of the plant. In addition, antimicrobial activities of the essential oils of S. brewpilum were investigated. The oils didn't show any antibacterial and antifungal activity against tested bacteria, but showed high antituberculostatic activity against Mycobacterium smegmatis

New Chalcone Derivative: Synthesis, Characterization, Computational Studies and Antioxidant Activity

Ozdemir, Namik/0000-0003-3371-9874WOS: 000505999500006A new chalcone derivative, called as 1-(4-(benzylideneamino)phenyl)-3-(furan-2-yl)prop-2-en-1-one (I), was synthezised and characterized by spectral methods (infrared (IR) and proton and carbon-13 nuclear magnetic resonance (H-1- and C-13-NMR) spectroscopy). A computational study was performed by the density functional theory (DFT) method. Spectral data of compound I optimized by using 6-311G(d,p) and 6-311++G(d,p) basis sets were obtained by 6-311++G(d,p) basis set. The E-Z isomerism for newly synthesized chalcone derivative was investigated by considering four isomeric form, E/E, E/Z, Z/E and Z/Z. The results show that, as assumed and thus named, the chalcone DOI: derivative is in the E/E form. In addition, quantum chemical parameters were calculated by using DFT method with 6-311++(d,p) basis set. Antioxidant activity of compound I was determined by the feiric reducing ability of plasma (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay methods. Compound I has low antioxidant activity.Karadeniz Technical UniversityKaradeniz Teknik UniversityThis study was supported by grants from Karadeniz Technical University

Biological evaluation and synthesis of new pyrimidine-2(1H)-ol/-thiol derivatives derived from chalcones using the solid phase microwave method

Alpay Karaoglu, Sengul/0000-0003-1047-8350; YUCEL, TAYYIBE BEYZA/0000-0002-2632-8325WOS: 000431245300026Twenty-five new hydroxy- and methoxy-substituted 4,6-diarylpyrimidin-2(1H)-ol (20-34) and 4,6-diarylpyrimidine-2(1H)-thiol derivatives (35-44) were synthesized from the reaction of the corresponding 1,3-diaryl-2-propene-1-one compounds (1-19) with urea or thiourea using the solid-phase microwave method. All the new synthetic compounds (20-44) were evaluated with regard to their \g=a\-glucosidase activity. However, only compounds 22-25, 27, 31, 34, 35, 37, and 40 exhibited a greater inhibitory effect than standard acarbose. The IC50 values of the active compounds ranged between 2.36 and 13.34 mu M. The 25 new compounds were also screened for their in vitro pancreatic lipase activity and compounds 20-27 and 35-39 were found to be active. Of these compounds 26, 27, and 39 exhibited the best antilipase activities at concentrations of 0.40 +/- 0.06, 0.26 +/- 0.07, and 0.29 +/- 0.026 mu M. All the new compounds (20-44) were evaluated for their in vitro antimicrobial activity for nine test microorganisms. Compounds 20-24 and 35-39 were determined to possess a significant broad spectrum against the gram-positive bacteria Escherichia faecalis, Staphylococcus aureus, and Bacillus cereus among the tested bacterial agents. Compounds 20-24 and 35-39 exhibit the best activity against Mycobacterium smegmatis, with minimum inhibitory concentrations of 62.5-500 mu g/mL, indicating their potential use as antituberculous agents.Karadeniz Technical University Research Fund, Turkey [KTU-BAP-02 FHD5395]This study was supported by grants from Karadeniz Technical University Research Fund (KTU-BAP-02 FHD5395), Turkey

Synthesis, antibacterial and antioxidant activities of new 1-alkyl-4-(1-alkyl-4-oxo-1,4-dihydroquinolin-2-yl)pyridinium bromides

AKAR, ZEYNEP/0000-0001-9262-8070WOS: 000330603900033PubMed: 24077525New 1-alkyl-4-(1-alkyl-4-oxo-1,4-dihydroquinolin-2-yl)pyridinium bromides (3a k) were synthesized from 1,4'-diazaflavone [2-pyridin-4-ylquinolin-4(1H)-one] and evaluated for antibacterial and antioxidant activities. A rapid one-pot preparation of 1,4'-diazaflavone (2) was done from 2'-amino substituted chalcone (1) by intramolecular Michael addition using solvent-free microwave heating. New N,N'-dialkyl substituted (C-5-C-15) 1,4'-diazaflavonium bromides were synthesized from compound 2 with corresponding alkyl halides. Compounds 3a k were active against six bacteria (MIC: 7.8-500.0 mu g/mL). They also showed good antioxidant activities in DPPI-1* scavenging (SC50: 45-133 mu g/mL) and ferric reducing/antioxidant power (14-141 p.M TEAC) tests. the biological activities decreased as alkyl chain length increased. the reason behind the obvious negative effect of alkyl chain elongation is unclear and requires investigations about the intermolecular interactions of these pyridinium salts with bioassay components. (C) 2013 Elsevier Masson SAS. All rights reserved.Karadeniz Technical UniversityKaradeniz Technical University; Scientific and Technological Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TUBiTAK-109T388]This study was supported by grants from Karadeniz Technical University and the Scientific and Technological Research Council of Turkey (TUBiTAK-109T388)

Synthesis of Novel Pyrazolines, Their Boron-Fluorine Complexes, and Investigation of Antibacterial, Antioxidant, and Enzyme Inhibition Activities

WOS: 000397305600003PubMed: 280326643,5-disubstituted-2-pyrazoline derivatives (4-6), their boron-fluorine complexes (boron (3-(2'-aminophenyl), 5-(2'-/3'-/4'-pyridyl) pyrazoline, BOAPPY) (7-9) and boron 1,2'-diazaflavone complex (BODAF) (11) were synthesized starting from azachalcones (1-3) to diazaflavone (10), respectively. Biological evaluation of compounds 4-9 and 11 showed remarkable antioxidant, antibacterial, and acetylcholinesterase and tyrosinase enzyme inhibition activities. All newly synthesized compounds 4-9 and 11 showed respectable antibacterial effect with minimum inhibitory concentrations in the range of 4.7-150mg/mL.Karadeniz Technical UniversityKaradeniz Technical University; Scientific and Technological Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TUBITAK-113T041]This study was supported by grants from Karadeniz Technical University and the Scientific and Technological Research Council of Turkey (TUBITAK-113T041)

Synthesis and biological evaluation of new 2,4,6-trisubstituted pyrimidines and their N-alkyl derivatives

Peker, Kivanc Derya Derya/0000-0002-8887-3505; aydin, ali/0000-0002-9550-9111WOS: 000458609100059PubMed: 30471580A series of new 2,4,6-trisubstituted pyrimidines and their N-alkyl bromide derivatives were prepared based upon methoxy substituted azachalcones as the starting materials. All newly synthesized compounds were screened for their anti-proliferative, cytotoxic, antibacterial activities and DNA/protein binding affinity. in vitro cell proliferation inhibitory and cell cytotoxic effects of 2,4,6-trisubstituted pyrimidines (1-9) and their N-alkyl bromide derivatives (2a-c, 3a-c, 5a-c, 6a-c, 8a-c, 9a-c) were obtained with the help of the 3[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) cell proliferation, LDH cytotoxicity detection, and microdilution assays. the antimicrobial activity for these compounds was also evaluated following the European Pharmacopoeia 8.0 protocol. the interactions of these compounds with DNA or bovine serum albumin were investigated by the spectrophotometric titration method. When the cytotoxic analysis and anticancer properties of the compounds were examined, most of the compounds significantly exhibited an anti-proliferative potency on cancer cells (IC50 similar to 2-10 mu g/mL) and caused a cytotoxic effect as low as control drugs, 5-fluorouracil, and cisplatin (similar to 7-15%). Because the compound-DNA adducts are hyperchromic or hypochromic, they caused variations in their spectra. This situation shows they can be linked to DNA by the groove binding mode at a binding constant range of 2.0 x 104 and 2.4 x 105 M-1. the antimicrobial screening results revealed that our new compounds for some human Gram( + ) and Gram( - ) pathogen bacteria showed remarkable activity with MIC values between < 7.81 and 125 mu g/mL. Overall, incorporation of alkyl chain to pyrimidines in the generation of N-alkyl bromides has resulted in showing differences in DNA/protein binding affinity, along with anti-proliferative and cytotoxic activity in favor of new compounds.Karadeniz Technical UniversityKaradeniz Technical University; Scientific and Technological Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TUBITAK-114R025]This study was supported by grants from Karadeniz Technical University and the Scientific and Technological Research Council of Turkey (TUBITAK-114R025)

Novel 2-amino-4-aryl-6-pyridopyrimidines and N-alkyl derivatives: Synthesis, characterization and investigation of anticancer, antibacterial activities and DNA/BSA binding affinities

aydin, ali/0000-0002-9550-9111WOS: 000535446600002PubMed: 32272366A series of new 2-amino-4-aryl-6-pyridopyrimidines, and their N-alkyl bromide derivatives were designed and synthesized by employing methyl substituted azachalcones. These novel compounds were evaluated and compared to the well-known chemotherapeutics in terms of their anti-cancer and anti-microbial functions, and their DNA/protein binding affinities. in order for the cell proliferation, cytotoxicity and microdilution features to be observed, various cancer cell lines (Hep3B, A549, HeLa, C6, HT29, MCF7) were treated with 2-amino-4-aryl-6-pyridopyrimidines (1-9) and their N-alkyl bromide derivatives (2a-c, 3a-c, 5a-c, 6a-c, 8a-c, 9a-c). Studies on the cells revealed that both pyrimidines and their alkyl derivatives (i) have a high anti-proliferative and antimicrobial activities, (ii) cause cell rounding, cytoplasmic blebs, and anomalous globular structure, and (iii) strongly bound to DNA/BSA macromolecules. Especially the length of the alkyl chain of the N-alkyl bromides has an increasing effect on the antiproliferative, antibacterial and cytotoxic functions, also DNA/protein binding affinity. Those results indicate the novel compounds to be promising antiproliferative agents, and their anticancer potential makes them candidates to be used for cancer therapy.Karadeniz Technical UniversityKaradeniz Technical University; Scientific and Technological Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TUBITAK-114R025]This study was supported by grants from Karadeniz Technical University and the Scientific and Technological Research Council of Turkey (TUBITAK-114R025)

Photophysical and photochemical study on novel axially chalcone substituted silicon (IV) phthalocyanines

AKCAY, Hakki Turker/0000-0002-8502-9608WOS: 000496810900091The novel axially chalcone bearing furan or thiphene groups substituted silicon (IV) phthalocyanine complexes were synthesized in this study. These novel phthalocyanines were characterized by general spectroscopic methods such as FT-IR, 1(H) NMR, UV-Vis, and MALDI-TOF. the aggregation behaviours of the synthesized phthalocyanines were investigated in different solvents and at different concentrations by UV-Vis spectroscopy. the aggregation behavior of the synthesized phthalocyanines were studied at different concentration and different solvents and it was observed chloroform and tetrahydrofuran solutions of furan substituted phthalocyanine (3a) show J-type aggregation as unusual. the photophysical and photochemical properties of the synthesized silicon(IV) phthalocyanine complexes were investigated in dimethylformamide (DMF). It was observed that although both of fluorescent and singlet oxygen quantum yields of the compounds were similar, thiophene substituted phthalocyanine Si(IV) complex show higher quantum yield (3b) than that of furan substituted (3a). (C) 2019 Published by Elsevier B.V

The Chemical Composition of the Essential oil, SPME and Antimicrobial Activity of Rhododendron caucasicum Pall.

The aim of this research was to investigate the effect of different extraction methods and chemical composition of the essential oil and solid-phase microextraction (SPME) from Rhododendrum caucasium Pall. The volatiles of R. caucasicum have been isolated by hydro distillation (HD) and SPME. The compositions of the volatiles were characterized by GC-FID/MS. A total of twenty-five and thirty-one compounds were identified constituting over 89.25%, and 90.33% of volatiles obtained with HD and SPME, respectively. The main volatile constituents of R. caucasicum were found to be calarene (46.13% (HD) and 54.91% (SPME)) and sandaracopimaradiene (25.93% (HD) and 8.16% (SPME)). Furthermore, the obtained essential oil (EO) and solvent extracts (n-hexane and methanol) of R. caucasicum were tested against the following nine bacteria: Escherichia coli, Yersinia pseudotuberculosis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Mycobacterium smegmatis, Candida albicans, and Saccharomyces cerevisiae. The EO showed moderate antimicrobial activities with the inhibition zone from 6 to18 mm against E. faecalis, S. aureus, B. cereus and M. smegmatis, respectively. Methanol extract gave better antimicrobial activity against the P. aeruginosa, E. faecalis, S. aureus, and B. cereus with the almost 15 mm inhibition zones