Antimicrobial and antioxidant activity evaluation of tetrazolo[1,5-a]pyrimidines: A simple diisopropylammonium trifluoroacetate mediated synthesis

Raju, C. M. Haricharan; Madhaiyan, Kalaipriya; Uma, R.; Sridhar, R.; Ramakrishna, Seeram

doi:10.1039/c2ra21330c

Cited by 37 publications

(20 citation statements)

References 34 publications

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“…Purine is an example of a fused pyrimidine ring exhibiting an attractive biological activity [3]. Tetrazolopyrimidine ring is an example of a fused heterocyclic ring that belongs to the purin analog, showing various biological activities [4] such as antioxidant, antimicrobial [5], anti-inflammation [6], antihepatitis [7], and anticancer [8]. Due to its broad spectrum of biological activity, developing a convenient and efficient synthesis method of tetrazolopyrimidine becomes an attractive challenge.…”

Section: Introductionmentioning

confidence: 99%

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5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Haq

Liawati

Abdulloh

et al. 2018

Molbank

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Section: Introductionmentioning

confidence: 99%

“…First is cyclization of a substrate possessing pyrimdine ring, such as ring closure in azidopyrimidine [9]. The second is cyclocondensation of a substrate possessing tetrazole ring, like a cyclocondensation reaction between chalcone [10] with 5-aminotetrazole or using a multicomponent reaction (Biginelli reaction) [5,11,12].…”

Section: Introductionmentioning

confidence: 99%

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Haq

Liawati

Abdulloh

et al. 2018

Molbank

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“…Tetrazolo[1,5- a ]pyrimidines have attracted attention in the pharmaceutical field due to their significant potential to exhibit antitumor, antimicrobial, and antioxidant activities [ 1 – 2 ]. In addition to acting as a stimulant of the central nervous system [ 3 ], this class of substances plays an important role in drugs that are used to treat obesity, diabetes, hypertension, coronary heart disease, thyroid cancer, and hepatitis B virus [ 4 – 13 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

Scapin

Salbego

Bender

et al. 2017

Beilstein J. Org. Chem.

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An efficient synthesis methodology for a series of tetrazolo[1,5-a]pyrimidines substituted at the 5- and 7-positions from the cyclocondensation reaction [CCC + NCN] was developed. The NCN corresponds to 5-aminotetrazole and CCC to β-enaminone. Two distinct products were observed in accordance with the β-enaminone substituent. When observed in solution, the compounds can be divided into two groups: (a) precursor compounds with R = CF3 or CCl3, which leads to tetrazolo[1,5-a]pyrimidines in high regioselectivity with R at the 7-position of the heterocyclic ring; and (b) precursor compounds with R = aryl or methyl, which leads to a mixture of compounds, tetrazolo[1,5-a] pyrimidines (R in the 5-position of the ring) and 2-azidopyrimidines (R in the 4-position of the ring), which was attributed to an equilibrium of azide–tetrazole. In the solid state, all compounds were found as 2-azidopyrimidines. The regiochemistry of the reaction and the stability of the products are discussed on the basis of the data obtained by density functional theory (DFT) for energetic and molecular orbital (MO) calculations.

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“…To the best of our knowledge, there is no published data about the interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole ( 5-AT ), although these reactions can be used to generate functionalized tetrazolo[1,5- a ]pyrimidines. Derivatives of these heterocycles are promising objects for biological testing, because substances possessing apoptotic and antitumor [ 13 ], antiviral [ 14 ], antimicrobial and antioxidant activity [ 15 ] have been found among them. The known tetrazolo[1,5- a ]pyrimidines were synthesized by cyclocondensation of 5-AT with 1,3-dicarbonyl compounds or their derivatives [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

Goryaeva¹,

Burgart²,

Ежикова³

et al. 2015

Beilstein J. Org. Chem.

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SummaryThe interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.

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Antimicrobial and antioxidant activity evaluation of tetrazolo[1,5-a]pyrimidines: A simple diisopropylammonium trifluoroacetate mediated synthesis

Cited by 37 publications

References 34 publications

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

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