Synthesis, characterization, antimicrobial activity, and QSAR studies on substituted oxadiazaboroles

Pir, Meryem; Ağirbaş, Hıkmet; Budak, Faik; Ilter, Merve

doi:10.1007/s00044-016-1603-1

Cited by 16 publications

(15 citation statements)

References 17 publications

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“…The measurements were carried out with low sample concentration (0.1 M) to reduce intermolecular effects. For the synthesis of compounds (1a-r), literature method [21] was applied and the spectral data of the compounds have been reported. All the statistical calculations were done by SigmaPlot program package.…”

Section: Methodsmentioning

confidence: 99%

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Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Pir¹,

Ağirbaş²,

Şahın³

2019

Journal of Boron

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Substituent effects on 1 H and 13 C NMR chemical shifts of 5-substituted phenyl-3-phenyl-4,5-dihydro-1,2,4,5-oxadiazaboroles (1a-r) were studied respectively. Single and duel substituent parameters were used for the correlation analysis of substituent-induced chemical shifts with σ, F and R constants. The calculations have shown the polar and resonance substituent effects on N-H proton and C=N carbon atoms. The ρ value was found positive for compounds (1a-r), which means that the substituent effect is normal. Additionally, crystal structure of compound (1i) was also studied. Density functional theory (DFT) calculations were carried out to calculate the theoretical chemical shifts, bond distances and bond angles.

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Section: Methodsmentioning

confidence: 99%

“…The values of 13 C=N and 1 H-N refer to the center peak of DMSO-d 6 which have the values of 39.50 ppm and 2.50 ppm for 13 C and 1 H respectively. The aromatic 1 H NMR and 13 C NMR chemical shifts, measured for oxadiazaborole compounds (1a-r) [21] are given in Table 6.…”

Section: Substituent Effects On 13 C=n and 1 H-n Chemical Shifts Of (1a-r)mentioning

confidence: 99%

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Pir¹,

Ağirbaş²,

Şahın³

2019

Journal of Boron

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“…Bu önemli biyolojik özellikler arasında antitüberküloz, antimikrobiyal, antibakteriyel, antifungal ve antiinflamatuar ajanlar ve HCV NS3 proteaz inhibitörleri olmaları sayılabilir. Özellikle B-O bağı içeren heterosiklik boron bileşikleri literatürde biyolojik aktivite gösteren önemli moleküllerdir [4][5][6][7][8][9][10][11][12]. Bu nedenle, sentezini gerçekleştirdiğimiz dioksaborepin (2a-c) bileşikleri de B-O bağı içerdiği için biyolojik aktiviteye [13] sahip olması beklenilen önemli bileşiklerdir.…”

Section: Bazı Dioksaborepin Türevlerinin Sentezi Ve Antimikrobiyal Aktivite Tayini Synthesis Of Some Dioxaborepine Derivatives and Determunclassified

“…'de verilmiştir. Bor içeren çeşitli bileşikler son yıllarda literatüre biyolojik aktif moleküller olarak girmiştir [4][5][6][7][8][9][10][11][12][13][20][21]. Örneğin; heterosiklik bor bileşiği olan oksadiazaborol bileşiklerinin antimikrobiyal aktivite çalışmasında MİK değerlerinin 12,5-800 μg/mL aralığında olduğu bildirilmiştir [12].…”

Section: Bu çAlışmada 3-(p-klorofenil)-cis-45bis(hidroksimetil)-45-dihidroisoksazolunclassified

Bazı Dioksaborepin Türevlerinin Sentezi ve Antimikrobiyal Aktivite Tayini

Pir¹

2021

Deu Muhendislik Fakultesi Fen Ve Muhendislik

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ÖzBu çalışmanın amacı, bazı dioksaborepin bileşiklerini (2a-c) sentezlemek ve (2a) bileşiği için çeşitli mikroorganizmalara karşı antimikrobiyal aktivite sonuçlarını değerlendirmektir. Mikrodilüsyon yöntemi için Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (ATCC 25923), Echerichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Streptococcus mutans (ATCC 25175) ve Candida albicans (ATCC 90028) kullanılmıştır. Dioksaborepin bileşiği (2a) özellikle hastane enfeksiyonuna neden olabilen P. aeruginosa'ya karşı iyi sonuç vermiştir. Dioksaborepin bileşiği (2a) Gram negatif ve Gram pozitif bakteriler ve mantara karşı aktivite göstermiştir. Bu çalışmadaki sonuçlara göre günümüzde, bor içeren yeni bileşiklerin sentezi ve aktivite testleri önemli bir yer tutmaktadır. Bu tür bileşikler geliştirilebilir ve gelecekte daha etkili, yeni antibakteriyel ve antifungal madde tasarımında kullanılabilirler.

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“…[18] Quantitative structureactivity/property relationship (QSAR/QSPR) is a commonly used computational technique for building predictive models that can discern the influence of significant molecular descriptors governing their biological activities and chemical properties. [16,19] Such QSAR models has been successfully employed for modeling a wide range of targets such as, antioxidant, [20][21][22] antimicrobial, [23][24][25][26] anticancer, [27,28] and antiviral [29,30] activities. As such, owing to the beneficial functions of QSAR models, herein, a large number of HCV inhibitors were used as the data set for the development of predictive models to facilitate rational drug design.…”

Section: Introductionmentioning

confidence: 99%

HCVpred: A web server for predicting the bioactivity of hepatitis C virus NS5B inhibitors

et al. 2020

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Hepatitis C virus (HCV) is one of the major causes of liver disease affecting an estimated 170 million people culminating in 300,000 deaths from cirrhosis or liver cancer. NS5B is one of three potential therapeutic targets against HCV (i.e., the other two being NS3/4A and NS5A) that is central to viral replication. In this study, we developed a classification structure–activity relationship (CSAR) model for identifying substructures giving rise to anti‐HCV activities among a set of 578 non‐redundant compounds. NS5B inhibitors were described by a set of 12 fingerprint descriptors and predictive models were constructed from 100 independent data splits using the random forest algorithm. The modelability (MODI index) of the data set was determined to be robust with a value of 0.88 exceeding established threshold of 0.65. The predictive performance was deduced by the accuracy, sensitivity, specificity, and Matthews correlation coefficient, which was found to be statistically robust (i.e., the former three parameters afforded values in excess of 0.8 while the latter statistical parameter provided a value >0.7). An in‐depth analysis of the top 20 important descriptors revealed that aromatic ring and alkyl side chains are important for NS5B inhibition. Finally, the predictive model is deployed as a publicly accessible HCVpred web server (available at http://codes.bio/hcvpred/) that would allow users to predict the biological activity as being active or inactive against HCV NS5B. Thus, the knowledge and web server presented herein can be used in the design of more potent and specific drugs against the HCV NS5B.

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Synthesis, characterization, antimicrobial activity, and QSAR studies on substituted oxadiazaboroles

Cited by 16 publications

References 17 publications

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Crystal structure, 1H and 13C NMR spectral studies of 1,2,4,5-oxadiazaborole derivatives

Bazı Dioksaborepin Türevlerinin Sentezi ve Antimikrobiyal Aktivite Tayini

HCVpred: A web server for predicting the bioactivity of hepatitis C virus NS5B inhibitors

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