Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles

Yavuz, Serkan; Aydin, Ozlem Celik; Çete, Servet; Dişli, Ali; Yıldırır, Yılmaz

doi:10.1007/s00044-009-9177-9

Cited by 12 publications

(9 citation statements)

References 13 publications

(15 reference statements)

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“…In particular, hydrazoic acid is profoundly toxic, explosive and volatile. Accordingly, there has been increased interest in modifying the methods of the preparation of tetrazoles (Amantini et al, 2004;Keith, 2006;Lakshmi Kantam et al, 2006a;Su et al, 2006;Hajra et al, 2007;Shie & Fang, 2007;Yavuz et al, 2010;Yildirir et al, 2013). The synthesis of different types of tetrazoles containing heteroatom has also become quite common (Özkan et al, 2007;Dişli & Salman, 2009).…”

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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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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“…21 The antimicrobial activity of substituted aniline have been reported. 22,23 In connection with such studies, the present paper reports for the first time the synthesis of 2-methyl-5-nitroaniline derivatives, 5a-5k and 6a-6f which are formed during the reaction of 2-methyl-5-nitroaniline (2) with different aldehydes, 3a -3k and different ketones, 4a -4f (Scheme 1). These synthesized compounds were characterized by elemental analyses, UV-visible, FT-IR, 1 H NMR and 13 C NMR studies.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 2‐Methyl‐5‐nitroaniline Derivatives: A Structure‐Activity Relationship Study

et al. 2011

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R ECE t a b r ~ JAN 0 5 1.995 1. SYNTHESIS AND 8ECEPTOR AFFINITIES OF NEW 3-QUINUCLIDINYL ALPHA-HETEROARYL-ALPHA-ARYL-ALPHA-HYDROXYACETATES (see Schemes in App. 1.1). Five analogues of 3-quinuclidinyl benzilate were prepared in which one phenyl ring was substituted by a heterocycle; a bromine was included on either the remaining phenyl or t h e heterocycle to provide information relating to the affinity of potential radiohalogenated derivatives. The required methyl 4-bromophenylglyoxalate (1) was synthesized from t h e reaction between 4-bromophenylmagnesium bromide with an excess of dimethyl oxalate a t-700 C. The reaction between ethyl oxalyl chloride with 2-bromothiphene provides ethyl 2-(5-bromothienyl)glyoxatate (2). Compounds (1) and (2) react with an equivalent amount of Grignard reagent to provide methyl or ethyl alpha-aryl-alpha-heteroarylglycolates (3). Transesterification of t h e methyl or ethyl esters (3) with (R,S)-3-quinuclidinol (4) in t h e presence of sodium metal provides t h e final products (5). A s a result of screening the novel compounds, we found a heterocyclic derivative of QNB that may surpass IQNB as a CNS receptor radioligand. This novel compound binds to mAChRs with an affinity that is greater than that of IQNB, i5 selective for the m l subtype, and is less lipophilic than IQNB, which should reduce t h e serum proteip binding relative to IQNB.[ [ [ (D I A LKY LA M I N 0) ALKYL]-1-PIPE RI D I N Y L] ACETYL]-1 0,l 1-D I HY D RO-5 H-D I B E N 20 [ b, e] [ 1,4] DIAZEPIN-1 1-ONES AS rn2-SELECTIVE ANTlMUSCARlNlCS (see Schemes in App. 1.2). The required 1 1-oxo-1 0,l 1-dihydro-5H-dibenzo[b,e] [1,4]diazepine (9) was prepared from the reaction between 2-chlorobenzoic acid and o-phenylenediamine. The reaction between 2-and 4-vinylpyridines (5 a , b) and dialkylamines (6a-e) provided 2-and 4-(dialkylamino)ethylpyridines (7). 4-Picolyllithium '(5~) reacted with 3-(dimethyl-or diethy1amino)propyl chloride to provide 4-[4-(dimethyl-or diethylamino) butyllpyridines (7). [(Dialkylamino)alkyl]pyridines-(7) were converted into the respective piperidines (8) by catalytic reduction(p1atinum oxide). Condensation of the tricycle (9) with chlocoacetyl chloride provided 5-(chloroacety1)-1 0,l 1-dihydro-SH-d i b e n z o [ b , e ] [ 1 , 4 ] d i a z e p i n-1 l-o n e (1 0). S u b s e q u e n t r e a c t i o n with [(dialkylamino)alkyl]piperidines (8) yielded t h e final products (4)-Compounds (4a-g,iIj) and two reference compounds (Table 111 in App. 1.2) were tested for their apparent affinities for the m l and m2 subtypes. Table 111 compares the selectivity and potency of these compounds to other compounds. These data demonstrate that (4j) is t h e most potent compound in the series. This compound is selective for m2 receptors over ml receptors by approximately 8-fold. These results also demonstrate t h a t (41) is approxhately 1 0 times more potent a t m2 receptors than AQ-RA 741. However, (4j) does not significantly penetrate the BBB. Cohen, Baumgold, Jin, de la Cruz, Rzeszotarski, Reba, J. Med. Chem. 36, ...

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“…Although tetrazoles moiety exhibits a wide and growing number of applications, they are not found in nature (Erkhtueva et al, 2013;Myznikov and Koldobskii, 2007). Several reports are present in the literature describing synthesis of tetrazoles (Patil et al, 2012;Shelkar et al, 2013;Ö zkan et al, 2007;Yavuz et al, 2010;Yıldırır et al, 2009;Shanmugam et al, 2013).…”

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 and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles

Cited by 12 publications

References 13 publications

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

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

Synthesis and Antimicrobial Activity of 2‐Methyl‐5‐nitroaniline Derivatives: A Structure‐Activity Relationship Study

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

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