Synthesis and antibacterial evaluations of new pyridazino[4,3‐e][1,3,4]oxadiazines

Bakavoli, Mehdi; Rahimizadeh, Mohammad; Shiri, Ali; Pordeli, Parvaneh; Pordel, Mehdi; Nikpour, Mohsen

doi:10.1002/jhet.398

Cited by 20 publications

(11 citation statements)

References 21 publications

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“…The 1,3,4‐oxadiazines represent an important type of six‐membered heterocycles with two adjacent nitrogen atoms. Many 1,3,4‐oxadiazine derivatives exhibit a great diversity of biological effects, such as antibacterial, antitumor, antileishmanial, miticidal, insecticidal, and monoamine oxidase (MAO) inhibitory activities . Some 1,3,4‐oxadiazine derivatives, e.g., indoxacarb, have been developed as a potent voltage‐dependent sodium channel blocker and have been widely used as a commercially successful insecticide .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4‐Oxadiazin‐5(6H)‐one Derivatives from Dehydroabietic Acid

Jin

Zhang

Chen

et al. 2018

J Chinese Chemical Soc

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A series of new 1,3,4‐oxadiazin‐5(6H)‐one derivatives (6a–n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF‐7, SMMC‐7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF‐7, SMMC‐7721, and HeLa cells, respectively, comparable to positive control etoposide.

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Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4‐Oxadiazin‐5(6H)‐one Derivatives from Dehydroabietic Acid

Jin

Zhang

Chen

et al. 2018

J Chinese Chemical Soc

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“…Regarding these points and as part of our ongoing studies dealing with the synthesis of various fused pyrimidines [28][29][30][31][32][33][34], herein, we wish to report on the synthesize of oxazolo [5,4-d] [1,2,4]triazolo [4,3-a]pyrimidine (5a-p) as members of a novel heterocyclic system that may be of use in designing new, potent and effective pharmacologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Oxazolo[5,4‐d][1,2,4]triazolo[4,3‐a]pyrimidines as a New Class of Heterocyclic Compounds

Akbarzadeh

Bakavoli

Shiri

2015

Journal of Heterocyclic Chem

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Several new derivatives of oxazolo [5,4-d]pyrimidine (3a-h) have been synthesized through the reaction of 2,4-dichloro-6-methyl-5-nitropyrimidine (2) with aryl carboxylic acids in refluxing POCl 3 . Further treatment of compounds (3a-h) with hydrazine hydrate gave the hydrazine derivatives (4a-h) that were subsequently cyclized into a novel heterocyclic system, oxazolo [5,4-d][1,2,4]triazolo[4,3-a]pyrimidine (5a-p) and (7a-d) on treatment with triethylorthoesters or carbondisulfide and alkylhalides, respectively. H NMR (CDCl 3 ): δ 2.89 (s, 3H, CH 3 of pyrimidine), 7.45 (t, J = 7.4 Hz, 1H, 2-chlorophenyl), 7.53 (t, J = 7.4 Hz, 1H, 2-chlorophenyl), 7.58 (d, J = 8.0 Hz, 1H, 2-chlorophenyl), 8.14 (d, J = 7.6 Hz, 1H, 2-chlorophenyl); 13 C NMR (CDCl 3 ): δ 165.2, 162.7, 160.7, 155.2, 834

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“…Based on these findings and in continuation of our studies on the synthesis of potentially bioactive heterocyclic compounds , we wish to report on the synthesis and regiochemistry of new pyrimido[4,5‐ e ][1,2,4]triazolo[3,4‐ b ][1,3,4]thiadiazine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Pyrimido[4,5‐e][1,2,4]triazolo[3,4‐b][1,3,4]thiadiazine Derivatives via S/N Smiles Rearrangement

Ebrahimpour

Shiri

Bakavoli

et al. 2015

Journal of Heterocyclic Chem

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Several new pyrimido[4,5‐e][1,2,4]triazolo[3,4‐b][1,3,4]thiadiazine derivatives (5a, 5b, 5c, 5d, 5e, 5f, 5g) were synthesized through the condensation reaction of 5‐bromo‐4,6‐dichloropyrimidine (1) and 4‐amino‐5‐methyl‐4H‐1,2,4‐triazole‐3‐thiol (2). The single crystal X‐ray data of one of the derivatives confirmed the occurrence of the S/N type Smiles rearrangement during the course of the reaction.

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Synthesis and antibacterial evaluations of new pyridazino[4,3‐e][1,3,4]oxadiazines

Cited by 20 publications

References 21 publications

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4‐Oxadiazin‐5(6H)‐one Derivatives from Dehydroabietic Acid

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4‐Oxadiazin‐5(6H)‐one Derivatives from Dehydroabietic Acid

Synthesis of Oxazolo[5,4‐d][1,2,4]triazolo[4,3‐a]pyrimidines as a New Class of Heterocyclic Compounds

Synthesis of New Pyrimido[4,5‐e][1,2,4]triazolo[3,4‐b][1,3,4]thiadiazine Derivatives via S/N Smiles Rearrangement

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