Synthesis, antimicrobial activity and cytotoxic investigation of novel trifluoromethylated tetrazolo[1,5-a]pyrimidines

Scapin, Elisandra; Frizzo, Clarissa P.; Rodrigues, Leticia V.; Zimmer, Geórgia C.; Vaucher, Rodrigo de Almeida; Sagrillo, Michele Rorato; Giongo, Janice Luehring; Afonso, Carlos A. M.; Rijo, Patrícia; Zanatta, Nilo; Bonacorso, Hélio G.; Martins, Marcos A. P.

doi:10.1007/s00044-017-1783-3

Cited by 15 publications

(8 citation statements)

References 32 publications

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“…To corroborate this result, compounds 6a , b , d – f (previously described in reference [ 37 ]) were evaluated from the solid state equilibrium point of view ( Fig. 4 ).…”

Section: Resultsmentioning

confidence: 69%

“…Some important structures for the current study are depicted in Table 3 . The results were correlated with LUMO coefficient data of β-alkoxyvinyl trifluoromethyl ketones, in which the first nucleophilic attack of the 5-aminotetrazole amino group occurs in the C4 [ 37 ]. The absence of the tetrazolo[1,5- a ]pyrimidine 2-azidopyrimidine equilibrium in solution in CDCl 3 or DMSO- d 6 , in this case, can be attributed to the presence of the CF 3 group at the 7-position of the ring.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, our research group demonstrated a highly regioselective synthesis of a series of trifluoromethylated tetrazolo[1,5- a ]pyrimidines with potent antimicrobial activity [ 37 ]. The reaction between several β-alkoxyvinyl trifluoromethyl ketones [CF 3 C(O)CH=C(R)OCH 3 ] (in which R = Ph, 4-F–C 6 H 4 , 4-Cl–C 6 H 4 , 4-Br–C 6 H 4 , 4-I–C 6 H 4 , 4-CH 3 –C 6 H 4 , 4-OCH 3 –C 6 H 4 , thien-2-yl, 4-Ph–C 6 H 4 , CH 3 ) and 5-aminotetrazole, by using conventional heating in an oil bath or microwave irradiation, was performed in IL.…”

Section: Resultsmentioning

confidence: 99%

“…To support this data, compound 6h , i (X = Cl) was synthesized using the methodology described in [ 37 ]. In a CDCl 3 or DMSO- d 6 solution, the compounds 6h , i were identified as tetrazolo[1,5- a ]pyrimidines (1,5-isomer).…”

Section: Resultsmentioning

confidence: 99%

“…In a manner closely related to a procedure from [ 37 ], a mixture of the 5-aminotetrazole (1.0 mmol) and the precursor β-enaminones 1 (1.0 mmol) in [BMIM][BF 4 ] (1.0 mmol) and HCl (0.1 mmol) were placed in a round-bottomed flask and magnetically stirred for 6 h at 120 °C. After the reaction time, chloroform (30 mL) was added and the resulting mixture was washed with distilled water (3 × 10 mL), dried over sodium sulfate (Na 2 SO 4 ), and the solvent was then removed under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

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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 corroborate this result, compounds 6a , b , d – f (previously described in reference [ 37 ]) were evaluated from the solid state equilibrium point of view ( Fig. 4 ).…”

Section: Resultsmentioning

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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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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(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

et al. 2020

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An efficient approach to the preparation of β‐alkoxyenones bearing (het)aryl difluoromethyl substituents is described. The method included acylation of acyclic or cyclic vinyl ethers with (het)aryl difluoroacetyl chlorides. The method worked well for most substrates, except aryl‐substituted derivatives bearing electron‐donating groups in o‐ or p‐positions, and heteroaromatic compounds bearing sufficiently basic nitrogen atom. Synthetic utility of (het)aryl difluoromethyl‐substituted β‐alkoxyenones as CCC bis‐electrophiles was demonstrated by heterocyclizations with common 1,2‐ and 1,3‐bis‐nucleophiles leading to compounds with (het)aryl–CF2–(het)aryl motif, in particular (het)aryl difluoromethyl‐substituted pyrazoles, isoxazoles, and pyrimidines – promising chemotypes for drug discovery.

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A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents

Hao

Cai

Zhang

et al. 2021

Journal of Heterocyclic Chem

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A series of aryldifluoromethyl pyrimidine compounds containing strobilurin were synthesized through bioelectronic isometric design with azoxystrobin as the lead compound and a convenient approach to aryldifluoromethylpyrimidine intermediates was developed, which features mild reaction conditions and simple operation. The title compounds and aryldifluoromethylpyrimidine intermediates were characterized by NMR and HRMS. Both 7c and 7l of the preliminary screening tests showed 100% inhibition against Mythimna separata at 100 mg/L. At 20 mg/L, the lethal rate of 7l against Mythimna separata can be up to 80%.

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Synthesis, antimicrobial activity and cytotoxic investigation of novel trifluoromethylated tetrazolo[1,5-a]pyrimidines

Cited by 15 publications

References 32 publications

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

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

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents

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