Regioselective bromination: Synthesis of brominated methoxyquinolines

Çakmak, Osman; Ökten, Salih

doi:10.1016/j.tet.2017.07.044

Cited by 14 publications

(30 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This study was carried out with substituted quinolines 3-13 according to our previous papers. [5,22,[24][25][26] In brief, the synthesis of 6-bromo-5nitroquinoline (4) and 5-nitro-3,6,8-tribromoquinoline (10) via direct nitration of 6-bromoquinoline (2) and 6-bromoquinoline-1-oxide (3) via N-oxidation of 2 with meta-chloroperbenzoic acid (m-CPBA) was reported recently in our previous publication. [24] The brominated methoxy and cynano quinolines (5-9, 11-12) starting from 6,8-dibromo-1,2,3,4-tetrahydroquinoline and 6,8-dibromoquinoline treating of NaOMe or CuCN and then bromide were synthesized according to our reported procedures.…”

Section: Synthesis Of the Substituted Quinoline Compoundsmentioning

confidence: 99%

“…[24] The brominated methoxy and cynano quinolines (5-9, 11-12) starting from 6,8-dibromo-1,2,3,4-tetrahydroquinoline and 6,8-dibromoquinoline treating of NaOMe or CuCN and then bromide were synthesized according to our reported procedures. [22,25,26] Furthermore, the synthesis of 6,8-diphenylquinoline (13) via Suzuki Coupling was reported in our recent work. [5] The isolated compounds 3-13 were fully characterized with melting point, HRMS analysis, infrared, 1 H, 13 C, heteronuclear multiple bond correlation (HMBC), and heteronuclear correlation spectroscopy (HETCOR) nuclear magnetic resonance (NMR) spectroscopy in these papers.…”

Section: Synthesis Of the Substituted Quinoline Compoundsmentioning

confidence: 99%

“…In our previous publications, we reported that brominated quinolines were easily functionalized by bromination of tetrahydroquinolines followed by transformation to their respective derivatives . We recently explored a new synthetic strategy to synthesize 6‐bromo, 6,8‐dibromo, and 3,6,8‐tribromoquinolines, based on the bromination of 1,2,3,4‐tetrahydroquinolines .…”

Section: Introductionmentioning

confidence: 99%

“…[20,21] In our previous publications, we reported that brominated quinolines were easily functionalized by bromination of tetrahydroquinolines followed by transformation to their respective derivatives. [4,6,22,23] We recently explored a new synthetic strategy to synthesize 6-bromo, 6,8dibromo, and 3,6,8-tribromoquinolines, based on the bromination of 1,2,3,4-tetrahydroquinolines. [23,25] In our previous studies, brominated tetrahydroquinolines were transformed to their respective derivatives, which were then tested for their anticancer potentials.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Köprülü

Ökten

Teki̇n³

et al. 2018

J Biochem & Molecular Tox

Self Cite

View full text Add to dashboard Cite

Due to a great deal of biological activities, quinoline derivatives have drawn attention for synthesis and biological activities in the search for new anticancer drug development. In this work, a variety of substituted (phenyl, nitro, cyano, N‐oxide, and methoxy) quinoline derivatives (3‐13) were tested in vitro for their biological activity against cancer cell lines, including rat glioblastoma (C6), human cervical cancer cells (HeLa), and human adenocarcinoma (HT29). 6‐Bromo‐5‐nitroquinoline (4), and 6,8‐diphenylquinoline (compound 13) showed the greatest antiproliferative activity as compared with the reference drug, 5‐fluorouracil (5‐FU), while the other compounds showed low antiproliferative activity. 6‐Bromo‐5‐nitroquinoline (4) possesses lower cytotoxic activity than 5‐FU in HT29 cell line. Due to its the apoptotic activity 6‐Bromo‐5‐nitroquinoline (4) has the potential to cause cancer cell death.

show abstract

Section: Synthesis Of the Substituted Quinoline Compoundsmentioning

confidence: 99%

Section: Synthesis Of the Substituted Quinoline Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Köprülü

Ökten

Teki̇n³

et al. 2018

J Biochem & Molecular Tox

Self Cite

View full text Add to dashboard Cite

show abstract

“…[3][4] Bromination of cyano-and methoxy-1,2,3,4-tetrahydroquinoline (5, 7, and 8) gave their corresponding 3-brominated quinoline derivatives (6, and 9-12, respectively) (Scheme 1). [4][5] We found that methoxy 1,2,3,4-tetrahydroquinolines (7,8) were brominated not only at the C-3, but also at the C-5 positions, to give the corresponding bromoquinolines. The quinoline moiety forms the key skeleton of several natural-product and pharmacologically-active compounds, displaying a broad spectrum of biological activities.…”

Section: Introductionmentioning

confidence: 99%

Activation of 6-bromoquinoline by nitration: synthesis of morpholinyl and piperazinyl quinolines

Çakmak¹,

Ökten²,

Alimli³

et al. 2018

Arkivoc

View full text Add to dashboard Cite

Quinoline forms the key skeletal component of a number of important natural products and pharmacologicallyactive compounds. Despite a tremendous amount of research pertaining to the derivatization of quinoline, very few general synthetic routes are described in the literature starting from quinoline or tetrahydroquinoline. A simple and convenient method for the polyfunctionalization of quinolines via nitration of bromoquinolines has been developed. This method represents a new synthetic approach to convert brominated nitroquinoline derivatives into useful cyclic amines via nucleophilic-substitution (SNAr) reaction.

show abstract

Synthesis, characterization, and SAR of arylated indenoquinoline‐based cholinesterase and carbonic anhydrase inhibitors

Ekiz

Tutar

Ökten

et al. 2018

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

We report the synthesis of bromoindenoquinolines (15a-f) by Friedlander reactions in low yields (13-50%) and the conversion of the corresponding phenyl-substituted indenoquinoline derivatives 16-21 in high yields (80-96%) by Suzuki coupling reactions. To explore the structure-activity relationship (SAR), their inhibition potentials to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase cyctosolic (hCA I and II) enzymes were determined. Monophenyl (16-18) indenoquinolines significantly inhibited the AChE and BChE enzymes in ranges of IC 37-57 nM and 84-93 nM, respectively, compared with their starting materials 15a-c and reference compounds (galanthamine and tacrine). On the other hand, these novel arylated indenoquinoline-based derivatives were effective inhibitors of the BChE, hCA I and II, BChE and AChE enzymes with K values in the range of 37 ± 2.04 to 88640 ± 1990 nM for AChE, 120.94 ± 37.06 to 1150.95 ± 304.48 nM for hCA I, 267.58 ± 98.05 to 1568.16 ± 438.67 nM for hCA II, and 84 ± 3.86 to 144120 ± 2910 nM for BChE. As a result, monophenyl indenoquinolines 16-18 may have promising anti-Alzheimer drug potential and 3,8-dibromoindenoquinoline amine (15f) can be novel hCA I and hCA II enzyme inhibitors.

show abstract

Regioselective bromination: Synthesis of brominated methoxyquinolines

Cited by 14 publications

References 24 publications

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Activation of 6-bromoquinoline by nitration: synthesis of morpholinyl and piperazinyl quinolines

Synthesis, characterization, and SAR of arylated indenoquinoline‐based cholinesterase and carbonic anhydrase inhibitors

Contact Info

Product

Resources

About