Aminotiyazollerin benzimidazol, benzotiyazol, benzofuran ve naftofuran türevlerinden yeni bileşiklerin sentezi ve antimikrobiyal etkilerinin değerlendirilmesi

The thiazole ring is the core of bioactive molecules that generate broad activity. These activities include anticonvulsant, antimicrobial, antituberculosis, antiviral, etc. In this work, starting from seconder/cyclic amines, new compounds containing thiazole and benzimidazole/benzothiazole/benzofurane/naphtofurane rings were synthesized, and their antimicrobial effects were evaluated. 9 compounds were synthesized by converting the seconder and cyclic amines to thiourea, and continued by thiazole ring closure. Ring closure was achieved by methylene-carbonyl condensation except conventional methods. Compound characterization was realized by FT-IR, 1 H NMR and 13C NMR and HRMS. Compounds did not show significant activity on bacterial strains. Nine aminothiazole derivatives have been synthesized successfully. Compounds did not show important antibacterial activity and thus were evaluated as inactive.Tiyazol halkası, birçok alanda biyolojik aktivite oluşturan moleküllerin çekirdeğidir. Bu aktiviteler arasında antikonvülsan, antimikrobiyal, antitüberküloz, antiviral vb. farmakolojik etkiler yer almaktadır. Bu çalışmada sekonder/siklik aminlerden yola çıkılarak tiyazol ve benzimidazol/benzotiyazol/benzofuran/naftofuran halkaları içeren yeni tiyazol türevleri sentezlenmiş ve antimikrobiyal etkileri değerlendirilmiştir. Bileşiklerin sentezinde, sekonder veya siklik aminler tiyoüreye dönüştürülerek 9 bileşik sentezlenmiş ve tiyazol halka kapanması ile devam edilmiştir. Halka kapatma, konvansiyonel yöntemler dışında metilen-karbonil kondenzassyonuyla gerçekleşmiştir. Bileşiklerin karakterizasyonu FT-IR, 1 H NMR ve 13C NMR ve HRMS ile gerçekleştirilmiştir. Bileşikler, bakteri suşları üzerinde önemli aktivite göstermedi. 9 aminotiyazol türevi başarıyla sentezlenmiştir. Bileşikler önemli bir antibakteriyel etki göstermediğinden inaktif olarak tanımlanmıştır

Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles

Heterocyclic compounds with diaryl substituents have been a milestone approach for selective cyclooxygenase 2 (COX 2) inhibition by bioisosteric replacements and modifications. It is also known that thiazole derivatives have different pharmacological activities. In this study, nine novel 2-[(1,5-diphenyl-1H-imidazole-2-yl)thio]-N-(thiazole-2-yl)acetamide derivatives (Compound 1-9) were synthesized via the reaction of 1,5-disubstitued phenyl-imidazole-2-thiole and N-thiazole acetamide. The inhibitory effects of COX-1 and COX-2 enzymes were tested for the synthesized compounds. Enzyme-ligand interactions of the most active compound on COX subtypes were elucidated by molecular modeling studies. The percent inhibitory effect for compound 1, which is the naked derivative among all the compounds, was found to be the most active on COX-2 at 10 mu M concentration (C1(COX-2): 88%, SC-560(COX-2): 98.2%, C1(COX-1): 60.9%); whereas compound 9 showed the highest inhibitory effect and was found to be the most selective derivative on COX-1 isoenzyme (C9(COX-1): 85%, DuP-697(COX-1): 97.2%, C9(COX-2): 57.9%)

Synthesis, antimicrobial and antioxidant activities of pyridyl substituted thiazolyl triazole derivatives

In this present study, 63 different 5-[4-methyl-2-(pyridin-3/4-yl)thiazole-5-yl]-4-substituted-3-substituted benzylthio-4H-1,2,4-triazole derivatives were synthesized, and evaluated for their in vitro antimicrobial activity against various human pathogenic microorganisms and antioxidant activity. The derivatives were synthesized in a multi-step synthesis procedure including triazole and thiazole ring closure reactions, respectively. The synthesized derivatives (A1-24; B1-39) were screened for their antibacterial, antifungal, and antioxidant activities compared to standard agents. The derivatives possessing 3-pyridyl moiety particularly exhibited relatively high antibacterial activity (MIC= < 3.09-500 µg/mL) against Gram-positive bacteria, and compounds possessing 4-pyridyl moiety showed remarkable antioxidant activity.Eskisehir Osmangazi Universit

Microwave supported synthesis of some novel 1,3-Diarylpyrazino[1,2-a] benzimidazole derivatives and investigation of their anticancer activities

WOS: 000286905400048PubMed ID: 21122952The syntheses of 1,3-diarylpyrazino[1,2-a]benzimidazole derivatives and the investigation of their anticancer activities were studied. For this, 2-aryloylbenzimidazole derivatives were reacted with 2-bromoacetophenones in acetone to give 1-(2-aryl-2-oxoethyl)-2-aryloylbenzimidazoles. The resulting materials were reacted with ammonium acetate in acetic acid to obtain the aimed compound. In this reaction, microwave irradiation method was applied as the reaction conditions. Anticancer activities of the compounds obtained were investigated. It was observed that some of the compounds showed remarkable anticancer activities

Synthesis and antitumor activity evaluation of new 2-(4-aminophenyl)benzothiazole derivatives bearing different heterocyclic rings

WOS: 000359815200017PubMed ID: 25198890Twenty-five new N-[4-(benzothiazole-2-yl)phenyl]acetamide derivatives bearing different heterocyclic ring systems were synthesized using 2-(4-aminophenyl)benzothiazole structure as a pharmacophoric group. Final compounds were screened for their potential antitumor activity in vitro against approximately 60 human tumor cell lines derived from nine neoplastic diseases at National Cancer Institute, USA. 2-(4-Aminophenyl)benzothiazole structure was prepared by the reaction of 4-aminobenzoic acid and 2-aminothiophenol in polyphosphoric acid using microwave irradiation. After acetylation reaction, amide compounds 2a and 2b were obtained, which were then reacted with 2-mercapto(benz)imidazole/benzothiazole/benzoxazole derivatives in acetone with the presence of potassium carbonate to gain final compounds (3-27). Among all tested compounds, compound 10, namely N-[4-(benzothiazole-2-yl)-3-chlorophenyl]-2-[(benzimidazole-2-yl)thio]acetamide, and compound 16, namely N-[4(benzothiazole-2-yl)phenyl]-2-[(1,5-diphenyl-1H-imidazole-2-yl)thio]acetamide, were found to be of considerable anticancer activity against some cancer cell lines.Commission of Scientific Research Projects of Eskisehir Osmangazi University [ESOGU/200819010]; Eskisehir Osmangazi UniversityThis work was supported by the Commission of Scientific Research Projects of Eskisehir Osmangazi University (ESOGU/200819010). The authors gratefully acknowledge the financial support by Eskisehir Osmangazi University

Synthesis of some N-[4-(benzothiazole-2yl)phenyl]-2-aryloxyacetamide derivatives and their anticancer activities

WOS: 000306524200007PubMed ID: 21823837In this study, some N-[4-(Benzothiazole-2-yl)phenyl]-2-aryloxyacetamide derivatives were prepared by reacting N-[4-(benzothiazole-2yl)phenyl]-2-chloroacetamide and different substituent phenol or thiophenol derivatives. The anticancer activities of the compounds obtained were investigated. It was observed that some of the compounds, namely 25 and 38, showed notable anticancer activity.Eskisehir Osmangazi University [ESOGU/200819010]This work was supported by the Commission of Scientific Research Projects of Eskisehir Osmangazi University (ESOGU/200819010). The authors gratefully acknowledge the financial support by Eskisehir Osmangazi University. Authors also would like to thank to National Cancer Institue (NCI), Bethesda, MD, USA for in vitro screening of our compounds in human cancer cell lines.Eskisehir Osmangazi Universit

Synthesis and antimicrobial activity evaluation of novel nitrofuranthiazoles

In this work, six novel 4-aryl-2-[2-((5-nitrofuran-2-yl)methylene)hydrazinyl] thiazole derivatives (2a-f) were synthesized starting from 5-nitro-2-furaldehyde diacetate by using Hantzsch thiazole synthesis. The antimicrobial activity of the title compounds were screened against five Gram positive bacteria B. cereus, E. faecalis, S. aureus, S. epidermidis, L. monocytogenes and two Gram negative bacteria E. coli and S. typhi. MIC and MBC were calculated and compared to standard drug nitrofurazone. Compounds bearing pyridine moiety (2d-e) exhibited significant antimicrobial activity which could be evaluated as new, potent antibacterial agents

Synthesis, antioxidant and antimicrobial properties of novel pyridyl-carbonyl thiazoles as dendrodoine analogs

Marine compound dendrodoine was first obtained from tunicate species (Dendrodo grossularia). It has a five-membered ring, namely, it is a heterocycle thiadiazole, which is found rarely in natural sources. Following its biological activities, novel analogs have been investigated recently. Synthesis of the analogs for this study is realized with uncommon thiazole closure, including methylene-carbonyl condensation. Structures are elucidated by NMR (H-1, C-13) and HRMS spectrums. As an alkaloid derivative, antioxidant properties were evaluated with DPPH and FRAP assays and antimicrobial effect with microclilution method. Among the series, 3bc-3cf showed higher antioxidant activity than those having 3 or 4-pyridyl substituents. There is lesser activity for 2-pyridyl activity for 2-pyridyl containing group, which may be a result of intramolecular interactions. No activity was observed against gram-negative bacteria at 250 mu g/mL. 3ae and 3ce showed activity at 64 mu g/mL against S. aureus and 3ae showed activity at 16 pg/ml. against S. epidermidis gram-positive bacteria. Chloramphenicol showed activity against all microorganisms at 8-16 mu g/mL. Sixteen original dendrodoine analogs have been defined by close/higher activity compared to dendrodoine analogs and Trolox

Synthesis, characterization and antibacterial evaluation of new pyridyl-thiazole hybrids of sulfonamides

Background and Aims: Sulfonamide drugs are a very old and noted group of small molecules, and are still one of the most important antimicrobial compounds. In this study, starting from sulfonamide drugs, new original compounds containing frequent and functional rings such as thiazole and pyridine were synthesized and their antimicrobial effects were evaluated. Methods: Eighteen new compounds were synthesized by converting the 4-amino group of the sulfonamides to thiourea, and continued by thiazole ring closure. Characterization of the compounds was carried out by FT-IR, H-1-NMR and C-13-NMR and HRMS. MIC values were obtained in antimicrobial activity studies, which were carried out by Broth Microdilution method. Results: Compounds 3p-r had an effect of 32 mu g/ml against B. spizizenii. In addition, compounds 3d-f and 3p-r each showed effect against different gram-positive bacteria. Compound 3r had an MIC of 128 mu g/mL against gram-negative organisms. The rest of the series did not affect gram-negative bacteria. In the study, chloramphenicol and sulfamethoxazole were used as standards. Conclusion: Sulfanilamide and sulfadiazine derivatives showed higher inhibitory effects compared to the rest of the series. 3d-f and 3p-r showed inhibitor activity against gram-positive bacteria, conversely to the standard drug sulfamethoxazole, which possibly means that the mechanism of action is not same