Synthesis and bacteriostatic properties of epoxybenzooxocino[4,3-b]pyridine derivatives

Stalinskaya, Alena L.; Martynenko, Nadezhda V.; Alkhimova, Larisa E.; Dilbaryan, Diana S.; Vasilchenko, Alexey S.; Dengis, Natalia A.; Vlasenko, V.S.; Кулаков, И. В.

doi:10.1016/j.molstruc.2022.134689

Cited by 5 publications

(4 citation statements)

References 67 publications

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“…This allows us to suppose the antiviral potential of the previously obtained epoxybenzo [7,8]oxocino [4,3-b]pyridine derivatives as synthetic analogues of natural integrastatins A, B. In addition, we also tested modified 5H-5,11-epoxybenzo [7,8]oxocino [4,3b]pyridine 3a derivatives for antiviral and bacteriostatic activity [24,25]. One of the synthesized compounds demonstrated high cytotoxicity and clear inhibition of the SARS-CoV-2 virus replication [24].…”

Section: Synlettmentioning

confidence: 99%

“…24 At the same time, a number of synthesized oxocino[4,3- b ]pyridine derivatives 3a showed pronounced and average antituberculosis activity along with moderate antibacterial and antifungal activity. 25 In this regard, the purpose of this study was to test the possibility of synthesizing pyrimidine structural analogues of natural integrastatins by the acid-catalyzed cyclization of salicylic aldehyde with pyrimidine 4-methyl-5-acetyl derivatives.…”

Section: Table 1 Reaction Of Pyrimidine 1...mentioning

confidence: 99%

“…In addition, we also tested modified 5H-5,11epoxybenzo [7,8]oxocino [4,3-b]pyridine 3a derivatives for antiviral and bacteriostatic activity. 24,25 One of the synthesized compounds demonstrated high cytotoxicity and clear inhibition of the SARS-CoV-2 virus replication. 24 At the same time, a number of synthesized oxocino [4,3-b]pyridine derivatives 3a showed pronounced and average antituberculosis activity along with moderate antibacterial and antifungal activity.…”

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confidence: 99%

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Synthesis of a New Heterocyclic System: Pyrimidine Structural Analogues of Natural Integrastatins A, B

Kulakov,

Chikunov,

Pustolaikina

et al. 2024

Synlett

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In this paper for the first time we report simple one-step synthesis of 5-methyl-11,12-dihydro-5H-5,11-epoxybenzo[7,8]oxocino[4,3-d]pyrimidine derivatives by acid-catalyzed cyclization reaction of various 4-methyl-5-acetyl pyrimidine derivatives with salicylic aldehyde. It was shown that 2-substituted 4-methyl-5-acetylpyrimidines successfully react to form a cyclization product. At the same time, 4-methyl-5-acetylpyrimidines with a substituent in the 6th position do not enter into the cyclization reaction. This may be caused by the negative effect of substituents in the 6th position, which hinder the free rotation of the acetyl group and prevent the formation of a stable pre-reaction complex. The structure of the obtained 5-methyl-11,12-dihydro-5H-5,11-epoxybenzo[7,8]oxocino[4,3-d]pyrimidine derivatives was confirmed using 1H, 13C spectroscopy, mass spectrometry and X-ray diffraction analysis.

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Section: Synlettmentioning

confidence: 99%

Section: Table 1 Reaction Of Pyrimidine 1...mentioning

confidence: 99%

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confidence: 99%

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Synthesis of a New Heterocyclic System: Pyrimidine Structural Analogues of Natural Integrastatins A, B

Kulakov,

Chikunov,

Pustolaikina

et al. 2024

Synlett

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“…Epoxybenzo[7,8]oxocino[4,3- b ]pyridine derivatives were synthesized and tested for antiviral and bacteriostatic activities in our previous works. 14 15 One of the synthesized compounds demonstrated high cytotoxicity and pronounced inhibition of SARS-CoV-2 viral replication. It was also shown that a series of synthesized oxocino[4,3- b ]pyridine derivatives perform pronounced and moderate antituberculous activity along with moderate antibacterial and antifungal activity.…”

Section: Synthesismentioning

confidence: 99%

Synthesis of New Structural Analogues of Natural Integrastatins with a Basic Epoxybenzo[7,8]oxocine Skeleton: Combined Experimental and Computational Study

Kulakov,

Stalinskaya,

Chikunov

et al. 2023

Synthesis

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In this work, the cyclization reactivity of various 3-acetyl-2-methylpyridines (including 3-acetyl-2-methylquinoline) containing both electron donor and acceptor substituents with salicylaldehyde into epoxybenzooxocino[4,3-b]pyridine derivatives was studied. The reactions were carried out in mild (under room temperature or reflux in 2-propanol) and harsh (in a sealed glass ampoule) conditions. It was shown that 3-acetyl-2-methylpyridines with an aryl substituent in the 4-position do not react with salicylaldehyde either under normal convection heating conditions or under more severe conditions. This effect was explained by the steric hindrance of the substituents using quantum chemical calculations. It was found that electron donor substituents in 3-acetyl-2-methylpyridines significantly facilitate cyclization in epoxybenzooxocino[4,3-b]pyridines. The presence of electron acceptor substituents (NO2 group for example) in the 5-position of pyridine prevents cyclization under normal conditions, but gives a rather high conversion to oxocinopyridines under more specific conditions. This effect is quantum-chemically explained by the decrease in the basicity of pyridine. Pyridines with two pairs of methyl groups in ortho-positions to the acetyl group are capable to form mixtures of regioisomeric epoxybenzooxocinopyridines. Further, epoxybenzooxocinopyridines with methyl and acetyl groups can form a mixture of diastereomeric bisoxocins under more specific conditions. All 17 initial pyridines were studied quantum-chemically in order to understand what features of their structure and properties affect the success of the cyclization reaction and the yield of the target product. The pyridine molecules were calculated by the DFT RB3LYP/6-311++G(d,p) method taking into account the alcohol solvent within the CPCM model using Gaussian-2016 program. It was shown that the absence of steric hindrances in the form of bulky substituents in 4-position of pyridines is the main factor affecting the success of the cyclization reaction. Also, the yield of the target product is affected by the CH-acidity of the methyl group in 2-position, which, in turn, is affected by electron-donating and electron-withdrawing substituents in the 5- and 6-positions.

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The synthesis and antitubercular activity of 4,5-dihydro-1H-pyrazole derivatives with a basic epoxybenzo[7,8]oxocine framework

Stalinskaya,

Dengis,

Vlasenko

et al. 2024

Chem Heterocycl Comp

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Synthesis and bacteriostatic properties of epoxybenzooxocino[4,3-b]pyridine derivatives

Cited by 5 publications

References 67 publications

Synthesis of a New Heterocyclic System: Pyrimidine Structural Analogues of Natural Integrastatins A, B

Synthesis of a New Heterocyclic System: Pyrimidine Structural Analogues of Natural Integrastatins A, B

Synthesis of New Structural Analogues of Natural Integrastatins with a Basic Epoxybenzo[7,8]oxocine Skeleton: Combined Experimental and Computational Study

The synthesis and antitubercular activity of 4,5-dihydro-1H-pyrazole derivatives with a basic epoxybenzo[7,8]oxocine framework

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