Living on pyrrolic foundations – Advances in natural and artificial bioactive pyrrole derivatives

Domagala, Anna; Jarosz, Tomasz; Łapkowski, Mieczysław

doi:10.1016/j.ejmech.2015.06.009

Cited by 127 publications

(46 citation statements)

References 115 publications

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“…Therefore, it is a good parent body to design new high-energy-density compounds. Pyrrole is found first in 1870, and it has been applied in a lot of fields including medicine, 11 natural molecule, 12 electroluminescence devices, 13 and so on. However, the application in the field of high-energy-density compounds is not entirely explored for the derivative of pyrrole until now, although the interaction between the nitro groups and the pyrrole ring has been proved to stable the derivatives effectively.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Calculations About the Thermal Stability and Detonation Character of Nitramino-Substituted Pyrrole

Li¹,

Li²,

Wang³

2020

Quim. Nova

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A series of nitramino-derivatives of pyrrole were designed through introducing the nitramino group into pyrrole ring to look for high-energy-density compounds. The molecular stabilities are explored thoroughly based on the calculated heats of formation, bond dissociation energy, and bond order at the B3PW91/6-311+G(d,p) level. The results indicated that the molecules designed in this paper have enough stability not only thermally but also kinetically. To evaluate the potential application as high-energy-density compounds, the detonation velocity and detonation pressure are calculated by using the Kamlet-Jacobs equation. Based on the calculation both of stability and detonation characters, four nitramino-derivatives of pyrrole (D1: 2,3-trinitramino-1H-pyrrole, D2: 2,3,4-trinitramino-1H-pyrrole, D3: 2,3,5-trinitramino-1H-pyrrole and E: 2,3,4,5-tetranitramino-1H-pyrrole) are screened out as potential high-energy-density molecules for further study.

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Section: Introductionmentioning

confidence: 99%

Theoretical Calculations About the Thermal Stability and Detonation Character of Nitramino-Substituted Pyrrole

Li¹,

Li²,

Wang³

2020

Quim. Nova

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“…[11] Meanwhile, ample evidences uggests that nitrogen-rich polyheterocycles may generatea bundant bioactivities. [12] But, to the besto fo ur knowledge,t here have been few reports to date on bioactivities of tetrahydropyrrole derivatives of resveratrol and other stilbenes, [13] because tetrahydropyrrolization is related to the generation of azomethine ylide. Meanwhile, theoretical calculations revealed that the hydrogen atoms at the a-position of tetrahydropyrrole canb ea bstractedb yr adicals.…”

Section: Introductionmentioning

confidence: 99%

Tetrahydropyrrolization of Resveratrol and Other Stilbenes Improves Inhibitory Effects on DNA Oxidation

Bao

Liu

2016

ChemMedChem

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The inhibitory effect of resveratrol on DNA oxidation caused by 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) was found to be enhanced if the C=C bond in resveratrol was converted into tetrahydropyrrole by reaction with azomethine ylide (CH2 =N(+) (CH3 )CH2 (-) ). This encouraged us to explore whether the inhibitory activities of other stilbenes could also be increased by the same method. We found that the inhibitory effects of the tetrahydropyrrole derivatives on AAPH-induced oxidation of DNA were higher than those of the corresponding stilbenes, because the tetrahydropyrrole motif can provide hydrogen atoms to be abstracted by radicals. Therefore, the tetrahydropyrrolization offered an advantage for enhancing the antioxidant effects of stilbenes. Notably, (CH3 )3 SiCH2 N(CH3 )CH2 OCH3 (in the presence of CF3 COOH) and (CH3 )3 NO (in the presence of LiN(iPr)2 ) can be used to generate azomethine ylide for the tetrahydropyrrolization of stilbenes containing electron-withdrawing and -donating groups, respectively.

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“…Pyrroles are among the most important five-membered heteroaromatic compounds that are ubiquitously found in natural products, bioactive compounds, and functional molecules [10][11][12][13][14][15] . Although diverse synthetic routes to substituted pyrroles have been continuously devised beyond the conventional Paal-Knorr and related methods, there is still an ample need for mild, efficient, selective, and short-step synthesis of highly substituted pyrroles [16][17][18][19][20][21] .…”

mentioning

confidence: 99%

Synthesis of pyrroles via ruthenium-catalyzed nitrogen-transfer [2 + 2 + 1] cycloaddition of α,ω-diynes using sulfoximines as nitrene surrogates

2018

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Pyrrole is a privileged five-membered aromatic nitrogen heterocycle, which is ubiquitous in natural products, drug molecules, and functional materials. Therefore, numerous synthetic routes to substituted pyrroles have been extensively developed. Nevertheless, the efficient and short-step synthesis of highly substituted and/or fused pyrroles has remained a significant challenge in organic chemistry. Here we report a ruthenium-catalyzed nitrogentransfer [2 + 2 + 1] cycloaddition of α,ω-diynes involving cyclic biscarbenoid intermediates. To achieve the key nitrogen transfer to carbenoid carbons, sulfoximines are employed as nitrene surrogates. Consequently, diverse fused pyrroles are successfully synthesized in good yields with wide functional group compatibility. Moreover, this method allows the synthesis of N-alkyl, N-aryl, and even N-H pyrroles, which are difficult to obtain using previous [2 + 2 + 1]-type reactions. Nitrogen transfer from sulfoximines to cyclic biscarbenoid intermediates is supported by density functional theory calculations and control experiments.

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Living on pyrrolic foundations – Advances in natural and artificial bioactive pyrrole derivatives

Cited by 127 publications

References 115 publications

Theoretical Calculations About the Thermal Stability and Detonation Character of Nitramino-Substituted Pyrrole

Theoretical Calculations About the Thermal Stability and Detonation Character of Nitramino-Substituted Pyrrole

Tetrahydropyrrolization of Resveratrol and Other Stilbenes Improves Inhibitory Effects on DNA Oxidation

Synthesis of pyrroles via ruthenium-catalyzed nitrogen-transfer [2 + 2 + 1] cycloaddition of α,ω-diynes using sulfoximines as nitrene surrogates

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