Synthesis of some novel amino and thiotetrazole purine derivatives and investigation of their antimicrobial activity and DNA interactions

Çelik, Gülay Dilek; Dişli, Ali; Öner, Yağmur; Açık, Leyla

doi:10.1007/s00044-012-0140-9

Cited by 29 publications

(3 citation statements)

References 24 publications

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“…1) in accordance with literature. Another known method for N(9) alkylation is using iodomethane, but in our hands Mitsunobu reaction produced lower amount of unidentifiable byproducts, and we obtained 2a,b with comparable or better yields than literature examples with iodomethane [13][14][15]. Boronic acids 5a,b were prepared from arylbromides 3a [16] and 3b [17] via metal-halogen exchange reaction with n-BuLi, followed by reaction with trimethyl borate and subsequent hydrolysis of borate ester (Fig.…”

Section: Resultsmentioning

confidence: 87%

Synthesis and Photophysical Properties of Purine-Phenoxazine and Purine-Phenothiazine Conjugates

Sebris

Traskovskis

Novosjolova

et al. 2021

KEM

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Electron donating phenoxazine and phenothiazine groups were introduced in an electron deficient purine structure through a benzene ring bridge to facilitate thermally activated delayed fluorescence. Mitsunobu and Suzuki-Miyaura reactions were used to synthesize the target compounds. Photophysical properties of target compounds were explored and quantum yields in the thin layer film reached up to 8 % and in the PMMA doped thin layer film up to 15 %.

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Section: Resultsmentioning

confidence: 87%

Synthesis and Photophysical Properties of Purine-Phenoxazine and Purine-Phenothiazine Conjugates

Sebris

Traskovskis

Novosjolova

et al. 2021

KEM

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“…Tetrazoles have a wide range of applications in pharmaceutical chemistry (Butler, 1984); they exhibit strong activities as anti-candida (Kaplancıklı et al, 2014a), antimicrobial (Yıldırır et al, 2009;Ç elik et al, 2013;Dişli et al, 2013), anti-proliferative (Kaplancıklı et al, 2014b), analgesic and antifungal preparations (Ahmad Malik et al, 2012). Furthermore, these nitrogenrich ring systems possess many applications in material science, including propellants (Damavarapu et al, 2010), explosives (Chen & Xiao, 1999) and photography (Frija et al, 2010).…”

Section: Introductionmentioning

confidence: 98%

facile, highly efficient and novel method for synthesis of 5-substituted 1H-tetrazoles catalysed by copper(I) chloride

2015

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The present study on tetrazole compounds, which have a wide area of application, proposes a new, simple and highly effective method. A series of 5-substituted 1H-tetrazoles were synthesised in DMF via the [3 + 2] cycloaddition reaction, in which different aryl nitriles with sodium azide were used and copper(I) chloride served as a catalyst. Short reaction times, high yields and simple procedures rendered this method attractive and useful for the organic synthesis of 5-substituted 1H-tetrazoles. A further advantage was the use of an environmentally friendly catalyst.

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“…We showed that these purine derivatives have antibacterial activity (Dilek-Celik et al, 2012). On the other hand, tetrazole attached purine bases disappeared their antimicrobial activity in another study (Dilek-Celik et al, 2013). But, all of these molecules contain 6-substituepurine derivatives incorporating different alkyl groups in position 9.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel purine derivatives incorporating tetrazole ring and investigation of their antimicrobial activity and DNA interactions

2014

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This work describes a novel purine derivatives incorporating tetrazole ring for biological applications. Initially, (6-aminopurin-9-yl)alkanenitrile compounds were synthesized. Then, 9-((1H-tetrazol-5-yl)alkyl)-9H-purin-6-amine compounds were synthesized via the addition of sodium azide to nitrile group. These novel purine analogues incorporating tetrazole ring were characterized by Fourier transform infrared, nuclear magnetic resonance and mass spectroscopic techniques. All the synthesized compounds were screened for their antibacterial activities against Gram-positive and Gram-negative bacteria and for their antifungal activities against yeast strains. The effect of the compounds on pBR322 plasmid DNA was studied by gel electrophoretic mobility measurements. The antibacterial activities and plasmid DNA interaction studies suggest that purine derivatives incorporating tetrazole ring cause DNA damages, and higher antibacterial activities than other derivatives.

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Synthesis of some novel amino and thiotetrazole purine derivatives and investigation of their antimicrobial activity and DNA interactions

Cited by 29 publications

References 24 publications

Synthesis and Photophysical Properties of Purine-Phenoxazine and Purine-Phenothiazine Conjugates

Synthesis and Photophysical Properties of Purine-Phenoxazine and Purine-Phenothiazine Conjugates

facile, highly efficient and novel method for synthesis of 5-substituted 1H-tetrazoles catalysed by copper(I) chloride

Synthesis of some novel purine derivatives incorporating tetrazole ring and investigation of their antimicrobial activity and DNA interactions

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