Microwave-assisted synthesis of some hybrid molecules containing penicillanic acid or cephalosporanic acid moieties and investigation of their biological activities

Alpay Karaoglu, Sengul/0000-0003-1047-8350WOS: 000334184400039Ethyl 4-amino-2-fluorophenylpiperazin-1-carboxylates containing a 1,3-oxazol(idin)e, 5-thioxo-1,2,4-triazole, 1,3,4-thiadiazole, 5-thioxo-1,3,4-oxadiazole, or 1,3-thiazole nucleus were obtained starting from ethyl piperazine-1-carboxylate (1) by several steps. the treatment of amine, 3 or hydrazide, 9 with several aromatic aldehydes generated the corresponding arylmethyleneamino (3a-f) or arylidenehydrazino (12a-c) compounds. the Mannich reaction between the 1,2,4-triazole or 1,3,4-oxadiazole compounds and 7-aca produced cephalosporanic acid derivatives. Penicillanic acid derivatives were obtained when 6-apa was used in the Mannich reactions. the synthesized compounds were screened for their antimicrobial, antilipase, and antiurease activities. Some of them were found to possess good-moderate antimicrobial activity against the test microorganisms. Two compounds exhibited antiurease activity, and four of them displayed antilipase activity.Scientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [107T333]; Karadeniz Technical University, BAP, TurkeyKaradeniz Technical University [8623]This Project was supported by Scientific and Technological Research Council of Turkey (TUBITAK, Project No: 107T333) and Karadeniz Technical University, BAP, Turkey (Ref. No. 8623) and is gratefully acknowledged

Synthesis and antimicrobial, antiproliferative evaluation of novel quinolone and conazole analogues via conventional and microwave techniques

1,2,4-Triazole-3-one (3), acquired from cinnamaldehyde was converted to the corresponding carbox(thio)amides via several steps (6 a–c). Their reaction with sodium hydroxide gave the 1,2,4-triazole derivatives (7 a–c). Compound 3 treatment with 2-bromo-1-(4-chlorophenyl) ethanone or 2-chloro-1-(2,4-dichlorophenyl)ethanone afforded the compounds 8 a,b and by reducing these compounds reduction products were obtained (9 a,b). The synthesis of (10 a–e) was carried out by the reaction compounds 9 a,b with different benzyl chlorides. Then oxadiazole derivative (12) was obtained by ring closure from hydrazide compound 5. Subsequently compounds 3, 7 a–c, and 12 were treated with various amines in the presence of formaldehyde to yield Mannich bases (11 a–e, 14 a–e, 13 a,b). Microwave-assisted and conventional techniques were utilized for the syntheses. The structures of newly synthesized compounds were illuminated by spectroscopic methods. Their antimicrobial (MIC method), and anticancer activities (Abay's method) were examined. Results showed that most of the compounds exhibited good antimicrobial activities. Especially compounds 14 a–e which is a mannich base showed very good antitubercular activity against Mycobacterium smegmatis compared with Streptomycin standard drug. Also compounds 8 a and 9 b have been found to have strong antiproliferative effects on the HeLa cervical cancer cells and also these compounds did not have a cytotoxic effects on a normal cells

Synthesis, characterization and cyclization reactions of some new bisthiosemicarbazones

The reaction of trans-1, 4-dichloro-2-butene 1 with selected phenols affords (E)-1, 4-bis(aryloxy)-2-butenes 2a-d which are converted into bis-thiosemicarbazones 3a-h via the reactions with thiosemicarbazide and 4-methyl thiosemicarbazide, respectively. Similarly, 4-methyl-5-ethoxycarbonyl- 2, 3-dihydro-1, 3-thiazoles 4a-h are synthesized via the reaction of bis-thiosemicarbazones 3a-h with ethyl 2-chloroacetoacetate. trans-1, 4-Dithiocyanato-2-butene 5 is obtained from the reaction of KSCN and trans-1, 4-dichloro-2-butene 1. Furthermore, the bis-2-amino-1, 3, 4-thiadiazoles 6k and l are obtained from the reaction of trans-1, 4-dithiocyanato-2-butene 5 with thiosemicarbazide and 4-methyl thiosemicarbazide, respectively. These compounds are characterized by elemental analyses, infrared, 1H-, 13C-NMR and mass spectrometry. Finally, the microbial features of all compounds are determined. Some of them exhibited microbial activities at low level, and the electronic absorption spectra of the compounds 3b, d, f and h are measured in organic solvents (MeOH, DMF, DMSO and 1, 4-dioxane) with various polarities

Farklı substratlar, pleurotus ostreatus'un antioksidan özelliklerini ve antimikrobiyal aktivitesini etkiler mi?

The aim of this study is to determine the effect of growing substrates on the antioxidant properties and antimicrobial activities of Pleurotus ostreatus (Jacq.) P. Kumm. In the study, growing substrates were prepared with five different tree sawdust (80%) and waste (20% Tea Waste or Wheat Bran) at different ratios (80% Sawdust + 20% TW, 80% Sawdust + 20% GW). The antimicrobial activities of methanol extracts from P. ostreatus grown on 19 different substrates were tested against microorganisms by agar well diffusion technique. The total phenolic content was measured by using the Folin-Ciocalteau procedure. The antioxidant capacity was determined by using ferric reducing antioxidant power (FRAP) and the free radical scavenging activity of DPPH. It was determined that the methanol extract of mushrooms obtained from the 80QS+20TW substrate was the most effective extract against all of the microorganisms investigated in this study. Significant differences (P<0.01) were found among extracts of mushrooms grown on different substrates. Total phenolic, FRAP and DPPH assay contents of methanol extracts from P. ostreatus varied between 1.016 to 4.772 mg GAE/g, 2.245 to 8.902 μmol FeSO4.7H2O/g, 4.650 to 22.922 mg/mL, respectively. The results of this study revealed that the substrate content affects the antioxidant properties and antimicrobial activities of P. ostreatus. In addition, it was observed that tea waste has a positive effect on antimicrobial activity when added to substrate.Bu çalışmanın amacı, yetiştirme substratlarının Pleurotus ostreatus (Jacq.) P. Kumm.’un antioksidan özellikleri ve antimikrobiyal aktiviteleri üzerindeki etkisini belirlemektir. Çalışmada beş farklı talaş türü (%80) ve atık (%20 Çay Atığı veya Buğday Kepeği) ile farklı oranlarda (%80 Talaş + %20 Çay atığı, %80 Talaş + 20% Buğday kepeği) yetiştirme substratları hazırlanmıştır. 19 farklı substrat üzerinde büyütülen P. ostreatus'tan elde edilen metanol ekstraktlarının antimikrobiyal aktiviteleri, agar kuyucuk difüzyon tekniği ile mikroorganizmalara karşı test edildi. Toplam fenolik içerik, Folin-Ciocalteau prosedürü kullanılarak ölçülmüştür. Antioksidan kapasitesi, ferrik indirgeyici antioksidan gücü (FRAP) ve DPPH'nin serbest radikal süpürücü aktivitesi kullanılarak belirlendi. 80QS+20TW substratından elde edilen mantarların metanol ekstraktının, bu çalışmada incelenen tüm mikrooganizmalara karşı en etkili ekstrakt olduğu belirlendi. Farklı substratlar üzerinde yetiştirilen mantar ekstraktlarının antioksidan içerikleri arasında önemli farklılıklar (P<0.01) bulundu. P. ostreatus'tan elde edilen metanol ekstraktlarının toplam fenolik, FRAP ve DPPH tahlil içerikleri, sırasıyla 1.016 ile 4.772 mg GAE/g, 2.245 ile 8.902 μmol FeSO4.7H2O/g, 4.650 ile 22.922 mg/mL arasında değişmiştir. Bu çalışmanın sonuçları, substrat içeriğinin, P. ostreatus'un antioksidan özelliklerini ve antimikrobiyal aktivitelerini etkilediğini ortaya koydu. Ayrıca çay atığı substrata eklendiğinde antimikrobiyal aktivite üzerinde olumlu bir etkiye sahip olduğu gözlenmiştir

Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus

2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (2) via the formation of ester (3) and then converted to the corresponding Schiff bases (5, 6) with the reaction with aromatic aldehydes. The carbothioamide (9), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (11) and 1,3,4-thiadiazole (12) derivatives by the treatment with NaOH or H2SO4, respectively. The cyclocondenzation of 9 with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (10) or 1,3-thiazolidine derivatives (13), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on M. smegmatis, and they displayed activity toward C. albicans and S. cerevisiae in high concentration. Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 +/- A 0.19 mu M

Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents

Three new series of 33 quinolone compounds, 2-(2-, 3-, and 4-fluorophenyl)-4-O-alkyl(C5&#8722;15) quinolines (7a– k, 8a–k, and 9a–k), were synthesized from 2-(2-, 3-, and 4-fluorophenyl)-2,3-dihydroquinolin-4(1H )-one (4, 5, and 6) by the reaction of alkyl halides under basic conditions in DMF. The new compounds 7a–k, 8a–k, and 9a–k were synthesized from flavonones 4–6, which can be considered new precursors for quinoline synthesis through a one-step reaction. All the target compounds (7a–k, 8a–k, and 9a–k) were evaluated for their in vitro antimicrobial activity against nine test microorganisms. They showed the most activity against Mycobacterium smegmatis with minimum inhibitory concentrations (MIC) of 62.5–500 µg/mL, indicating their potential uses as antituberculosis agents. Among them 8a–k (m-fluoride) were the most active compounds against M. smegmatis (MIC, 62.5–125 µg/mL). The newly synthesized title compounds were also evaluated for their in vitro antioxidant activities using DPPH• radical scavenging and FRAP tests. They showed at a low concentration (mg/mL) a range of SC50 values of 0.03–12.48 mg/mL (DPPH•) and 0–722 µM (FRAP), respectively. The antioxidant results of compounds 7a–k, 8a–k, and 9a–k revealed that the length of the alkyl chain was negatively correlated with antioxidant capacity

Isolation, characterization, and genetic diversity of Paenibacillus larvae from AFB suspected specimens in the Central and Eastern Black Sea Regions

American foulbrood is an important bacterial disease affecting the larvae of honey bees (Apis mellifera L.) caused by Paenibacillus larvae. Due to easy transmission of disease and the ability of bacteria to create spores, it is a bacterium resistant to both physical and chemical conditions. The study aims to isolate, perform microbiological analyses, and determine biochemical properties and genotypes P. larvae strains from AFB samples collected from Turkey's Central and Eastern Black Sea regions. An isolation study was conducted on adult bees, larvae, honey, and primary honeycomb samples from suspected colonies in the regions under study. After the purification of bacterial isolates from samples, P. larvae strains were identified using biochemical and molecular methods. The genetic diversity and ERIC types of P. larvae isolates were determined by rep-PCR DNA genotyping using BOX A1R and MBO REP1 primers and multiplex-PCR. A phylogenetic tree of P. larvae strains was constructed in the study. All P. larvae isolates were determined as ERIC I type. According to the rep-PCR results of P. larvae strains, 15 of the 28 isolates were Ab genotype (54%), 7 (25%) Aβ genotype, 4 (14%) AB genotype, 1 (3.5%) αB genotype, and 1 (3.5%) ab genotype. From an epidemiological viewpoint, it was determined that Ab and Aβ genotypes were widely distributed, while other genotypes (AB, αB, and ab) showed less spread. The results of the study will guide researchers in taking relevant measures to prevent and control American foulbrood. © 2023, The Author(s), under exclusive licence to Plant Science and Biodiversity Centre, Slovak Academy of Sciences (SAS), Institute of Zoology, Slovak Academy of Sciences (SAS), Institute of Molecular Biology, Slovak Academy of Sciences (SAS)

Chemical composition and antimicrobial activity of the essential oils of five Scrophularia L. Species from Turkey

The essential oils of the five Scrophularia species; Scrophularia chrysantha Jaub. et Spach, Scrophularia kotschyana Benth., Scrophularia olympica Boiss., Scrophularia cinerascens Boiss. and Scrophularia zuvandica Grossh. were obtained by hydrodistillation (HD) with a range of 0.10% to 0.16% yield and analazsed by GC-FID/MS. In the meantime, the volatile organic compounds (VOCs) of S. chrysantha, S. kotschyana, S. olympica, S. cinerascens and S. zuvandica were also identified with the technique of SPME GCFID/MS and the phytochemical results were evaluated. The experimental results of this study showed that the major compounds of essential oils which were taken by the hydrodistillation were carvacrol (52.4%), 2pentadecanone (26.7%), 2-pentadecanone (12.2%), (Z)-2-nonenal (11.2%) and carvacrol (69.1%) respectively. Isovaleraldehyde (37.1%, 27.9%), eucalyptol (13.8%), 2-ethyl furan (14.8%) and 3(Z)-hexenol (91.3%) were respectively found as the main constituents of the five Scrophularia species with SPME method. Also antimicrobial activities of the essential oils of the five Scrophularia species were screened by using agar well diffusion method. It was identified that S. olympica, S.chrysantha, and S. kotschyana, have anti-tuberculosis activity, whereas, the essential oils gained from S. zuvandica and S. cinerascens have anti-fungal activit

Chemical constituents and antimicrobial activities of the essential oils from Sedum pallidum var. bithynicum and S. spurium grown in Turkey

PubMed: 20645839Chemical compositions of the essential oil of Sedum pallidum Bieb. var. bithynicum (Boiss.) and S. spurium Bieb. (Crassulaceae) from Turkey were investigated by GC-MS, and antimicrobial activity of the oil samples were assessed against Gram-positive/negative bacteria and yeast-like fungi. Thirty-eight and thirty-five components were identified in the essential oils and the main components of these species were found to be caryophyllene oxide from S. pallidum var. bithynicum and hexahydrofarnesyl acetone from S. spurium in the ratios of 12.8% and 15.7%, respectively. The isolated essential oils of the plants showed low antimicrobial activity against Gram-negative/positive bacteria and yeast-like fungi, having the MIC values of 500-2000?g/mL. Antibacterial activity was not observed against Bacillus cereus. © 2010 Informa UK Ltd.Karadeniz Teknik ÜniversitesiThis study was supported by grants from Karadeniz Technical University and State Planning Agency (DPT) of Turkey.Karadeniz Teknik Üniversitesi ve Türkiye Devlet Planlama Teşkilatı (DPT

Antibacterial activity of bryophyte species against Paenibacillus larvae isolates

This study was performed to determine the antibacterial activity of methanol extracts of 23 bryophyte species against Paenibacillus larvae isolates that cause American foulbrood diseases in honeybee larvae. The honey and larva samples were collected from nine different locations of Rize in Turkey. A total of 22 gram-positive spore-forming bacteria were isolated from the larva and honey samples. According to the results of morphological, biochemical, and molecular (16S rRNA gene sequencing) tests, 10 isolates of the 22 gram-positive spore-forming bacteria were identified as P. larvae. A total of 10 bryophyte species (Polytrichum formasum,Polytrichum commune, Calliergonella cuspitada, Calliergonella lindbergi, Metzgeria conjugata, Isothecium alopecuroides, Syntrichia calcicola, Syntrichia intermedia, Tortella densa,and Grimmia alpestris) among 23 bryophytes showed good antimicrobial activity against P. larvae isolates according the results of agar-well diffusion method and minimal inhibition concentration experiments