Synthesis of pyrrolo[3,2-c]carbazole-2-carbohydrazides and pyrrolo[3,2-c]carbazol-2-yl-1,3,4-oxadiazoles and their <i>in vitro</i> antibacterial evaluation

Sağlam, Mehmet F.; Gündoğdu, Aycan; Hora, Mehmet; Kandemir, Hakan; Sengul, İbrahim F.

doi:10.1080/00397911.2021.1966040

Cited by 3 publications

(3 citation statements)

References 33 publications

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“…Reports on the synthesis and reactivity of pyrrolo[3,2- c ]carbazoles are scarce. Recently, however, a few reports describing the synthesis ( Benzi et al, 2019 ), photophysical and biological activity, namely, antioxidant ( Bingul et al, 2019 ), anticancer and antibacterial activity, have been disclosed ( Sengul et al, 2016 ; Saglam et al, 2021 ; Sinicropi et al, 2021 ). Compound 9 is an example of a pyrrolo[3,2- c ]carbazole with high cytotoxicity against human colon cancer HT29 cells ( Sengul et al, 2016 ).…”

Section: Introductionmentioning

confidence: 99%

Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]carbazole: an experimental and theoretical study

et al. 2023

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Nitrosoalkenes react with 8-methyl-1,6-dihydropyrrolo[3,2-c]carbazole to give both 2- and 3-alkylated products via hetero-Diels-Alder reaction followed by the cycloadduct ring-opening. Quantum chemical calculations, at DFT level of theory, were carried out to investigate the regioselectivity of the cycloaddition of ethyl nitrosoacrylate with 1,6-dihydropyrrolo[3,2-c]carbazoles as well as with pyrrole and indole, allowing a more comprehensive analysis of the reactivity pattern of nitrosoalkenes with five-membered heterocycles. Furthermore, theoretical calculations confirmed that ethyl nitrosoacrylate reacts with these heterocycles via a LUMOheterodiene-HOMOdienophile controlled cycloaddition. The reactivity of one of the oxime-functionalized 1,6-dihydropyrrolo[3,2-c]carbazole was explored and a new hexahydropyrido[4′,3':4,5]pyrrolo[3,2-c]carbazole system was obtained in high yield via a one-pot, two-step procedure.

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Section: Introductionmentioning

confidence: 99%

Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]carbazole: an experimental and theoretical study

et al. 2023

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“…

B y virtue of existing various important biological activities, there has been a growing interest over the past decades for the synthesis of nitrogen containing heterocycles [1][2][3][4][5]. Among these heterocycles, benzimidazole and carbazole platforms are important type of nitrogen possessing building blocks due to their diverse range of biological activity [5][6][7][8][9][10].Benzimidazole is benzene and imidazole fused with a bicyclic aromatic compound. The NH functional group in the benzimidazole scaffold is quite weakly primary and relatively strong acidic.

…”

mentioning

confidence: 99%

“…B y virtue of existing various important biological activities, there has been a growing interest over the past decades for the synthesis of nitrogen containing heterocycles [1][2][3][4][5]. Among these heterocycles, benzimidazole and carbazole platforms are important type of nitrogen possessing building blocks due to their diverse range of biological activity [5][6][7][8][9][10].…”

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confidence: 99%

Synthesis, Characterization and Thermal Analysis of Novel Methylene Bridged Bis-carbazole Based Bisbenzimidazoles

Sağlam¹

2022

Hittite Journal of Science and Engineering

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The synthesis of novel bis(3-carbazoly1)methane linked bis-benzimidazoles is described. Construction of symmetrical bis-benzimidazoles on the bis-carbazolylmethane scaffold was succeeded by condensation reaction of benzene-1,2-diamine derivatives with bis(9-ethyl-9H-carbazole-3-carbaldehyde). The structural analysis of the targeted compounds 4-7 were confirmed by NMR, FT-IR spectroscopy and mass spectrometry. The thermal stability of final products 4-7 was also studied by thermogravimetric analysis (TGA).

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Antimicrobial activity of natural and semi-synthetic carbazole alkaloids

Ding,

Zhou,

Peng-Deng

et al. 2023

European Journal of Medicinal Chemistry

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Synthesis of pyrrolo[3,2-c]carbazole-2-carbohydrazides and pyrrolo[3,2-c]carbazol-2-yl-1,3,4-oxadiazoles and their in vitro antibacterial evaluation

Cited by 3 publications

References 33 publications

Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]carbazole: an experimental and theoretical study

Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]carbazole: an experimental and theoretical study

Synthesis, Characterization and Thermal Analysis of Novel Methylene Bridged Bis-carbazole Based Bisbenzimidazoles

Antimicrobial activity of natural and semi-synthetic carbazole alkaloids

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