Synthesis of fluorinated carbazoles via C–H arylation catalyzed by Pd/Cu bimetal system and their antibacterial activities

Kong, Xianqiang; Zhang, Huizi; Cao, Changsheng; Zhou, Shengliang; Pang, Guangsheng; Shi, Yanhui

doi:10.1016/j.bmc.2016.02.013

Cited by 15 publications

(7 citation statements)

References 27 publications

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“…was screened in dry toluene at 100 °C. Aromatic amines such as pyridine, quinoline, and acridine were found to be ineffective, both in absence and presence of CuI as additive, while 2,6‐lutidine afforded traces of carbazole 4 a , only in presence of CuI (Table , entry 1). Use of aliphatic amines, TEA and DIPEA showed some carbazole formation although with poor conversions, and only when used with CuI; however significant conversion increase was observed with DABCO and particularly with DBU; the latter proved equally efficient in presence or absence of CuI, whereas DABCO was found more efficient in the presence of CuI, even though it remains less efficient than DBU (entries 2–7).…”

Section: Resultsmentioning

confidence: 99%

“…This methodology was restricted to methyl 3‐iodo‐4‐(arylamino)benzoates, bearing mainly alkoxy substituents; and preparation of carbazoles without the carbomethoxy group at para ‐position of the ortho ‐iodophenyl ring was not investigated. More recently, Shi et al . described the synthesis of fluorinated carbazoles from 2‐bromo‐ N ‐arylanilines using the Pd/Cu bimetallic system in presence of NaO t Bu at 120 °C.…”

Section: Introductionmentioning

confidence: 99%

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Mild and Efficient Synthesis of Functionalized Carbazoles via a DBU‐Assisted Sequence Involving Cu‐ and Pd‐Catalyzed Coupling Reactions

et al. 2019

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Practical access to diversely functionalized carbazoles has been developed by consecutive Cu-catalyzed Chan-Lam NÀ arylation of various o-iodoanilines and boronic acids, and Pd-catalyzed intramolecular aryl CÀ H activation of 2-iodo-N-arylanilines. Use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base was found beneficial for both steps. In the Pd-catalyzed CÀ H activation step, DBU acts as ligand as well as base, resulting in improved functional tolerance and higher yields than those observed with inorganic or other nitrogen bases. This DBU-assisted sequence offers access to a variety of carbazoles with various electron-donating and electron-withdrawing substituents, including halogens or other reactive functional groups. Twentyseven cabazoles with various substitution paterns, including two naturally-occurring carbazoles -clausine L and clausine Hhave been successfully synthesized using these DBU-promoted metal-catalyzed coupling reactions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mild and Efficient Synthesis of Functionalized Carbazoles via a DBU‐Assisted Sequence Involving Cu‐ and Pd‐Catalyzed Coupling Reactions

et al. 2019

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“…Streptomycin was used as a reference control at concentrations of 50, 25, 12.5, 6.25, 3.12, 1.56, 0.78, 0.39 µg/mL. Streptomycin is a broad spectrum antibiotic which inhibits the growth of both Gram-positive and Gram-negative bacteria and has been widely used as a reference [41,42]. In order to ensure that the solvent had no effect on bacterial growth, a control test was also performed containing inoculated broth supplemented with different concentrations (1%–16%) of DMSO.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

et al. 2016

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A number of 1,2-benzothiazines have been synthesized in a three-step process. Nine chalcones 1-9 bearing methyl, fluoro, chloro and bromo substituents were chlorosulfonated with chlorosulfonic acid to generate the chalcone sulfonyl chlorides 10-18. These were converted to the dibromo compounds 19-27 through reaction with bromine in glacial acetic acid. Compounds 19-27 were reacted with ammonia, methylamine, ethylamine, aniline and benzylamine to generate a library of 45 1,2-benzothiazines 28-72. Compounds 28-72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium; however, compounds 31, 33, 38, 43, 45, 50, 53, 55, 58, 60, 63 and 68 showed activity against Gram-positive bacteria Bacillus subtilis and Staphylococcous aureus. The range of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was 25-600 µg/mL, though some of the MIC and MBC concentrations were high, indicating weak activity. Structure activity relationship studies revealed that the compounds with a hydrogen atom or an ethyl group on the nitrogen of the thiazine ring exerted antibacterial activity against Gram-positive bacteria. The results also showed that the compounds where the benzene ring of the benzoyl moiety contained a methyl group or a chlorine or bromine atom in the para position showed higher antimicrobial activity. Similar influences were identified where either a bromine or chlorine atom was in the meta position.

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“…Many natural products or their derivatives have been demonstrated to have extensive antitumor activities by inducing apoptosis ( Chen et al, 2015 ; Liu et al, 2015 ; Padmaja et al, 2015 ; Bailly, 2020 ; Greco et al, 2021 ) and inhibiting mitosis ( Thomas et al, 2016 ; Davison and Sperry, 2017 ; Yokoyama et al, 2019 ). As an important class of aromatic heterocyclic compounds, carbazole alkaloid derivatives have long been used in medicinal chemistry ( Murali et al, 2017 ; Sun et al, 2017 ; Zhou et al, 2018 ; Cao et al, 2019 ; Issa et al, 2019 ; Liu et al, 2019 ; Rassias et al, 2019 ; Liu et al, 2020 ; Liu et al, 2021 ; Wang et al, 2022 ), agrochemicals ( Kong et al, 2016 ; Wang et al, 2017 ; Dang et al, 2018 ; Sun et al, 2020 ; Xie et al, 2020 ) and other fields. So, how to realize the functional modification of carbazole ring to improve its activity is always an important research direction.…”

Section: Introductionmentioning

confidence: 99%

Structural diversity-guided optimization of carbazole derivatives as potential cytotoxic agents

et al. 2023

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Carbazole alkaloids, as an important class of natural products, have been widely reported to have extensive biological activities. Based on our previous three-component reaction to construct carbazole scaffolds, we introduced a methylene group to provide a rotatable bond, and designed series of carbazole derivatives with structural diversity including carbazole amide, carbazole hydrazide and carbazole hydrazone. All synthesized carbazole derivatives were evaluated for their in vitro cytotoxic activity against 7901 (gastric adenocarcinoma), A875 (human melanoma) and MARC145 (African green monkey kidney) cell lines. The preliminary results indicated that compound 14a exhibited high inhibitory activities on 7901 and A875 cancer cells with the lowest IC50 of 11.8 ± 1.26 and 9.77 ± 8.32 μM, respectively, which might be the new lead compound for discovery of novel carbazole-type anticancer agents.

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Synthesis of fluorinated carbazoles via C–H arylation catalyzed by Pd/Cu bimetal system and their antibacterial activities

Cited by 15 publications

References 27 publications

Mild and Efficient Synthesis of Functionalized Carbazoles via a DBU‐Assisted Sequence Involving Cu‐ and Pd‐Catalyzed Coupling Reactions

Mild and Efficient Synthesis of Functionalized Carbazoles via a DBU‐Assisted Sequence Involving Cu‐ and Pd‐Catalyzed Coupling Reactions

Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

Structural diversity-guided optimization of carbazole derivatives as potential cytotoxic agents

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