An efficient reduction of azide to amine: a new methodology to synthesize ethyl 7-amino-1-ethyl-6,8-difluoroquinolone-3-carboxylate and its spectroscopic characterization

Leyva‐Ramos, Socorro; Hernández‐López, Hiram; Jiménez-Cataño, Rogelio; Chacón-Garcı́a, Luis; Vega-Rodríguez, Sarai

doi:10.1007/s11696-016-0016-4

Cited by 3 publications

(2 citation statements)

References 31 publications

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“…Subsequent catalytic reduction of the nitro group yields the desired amino group. Reducing an azide group at the C‐7 position [42–44] can also produce amine moieties. Azides are essential intermediates in medicinal chemistry, enabling the synthesis of heterocycles such as triazoles and tetrazoles, allowing quinolone‐triazole or tetrazole hybrids to be generated [45–48] …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Hernández‐López,

Tejada‐Rodríguez,

Leyva‐Ramos

et al. 2023

ChemistrySelect

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Novel 1‐(ethyl/methyl)‐7‐(p‐methoxybenzyl amino) and 7‐amino‐6‐fluoroquinolone‐boron difluoride complexes were synthesized, and their biological activity was studied, comparing the influence of the nature of 7‐substituent as well as N‐1 substituent. The quinolone compounds were characterized by IR, UV‐Vis, 1H, 13C{1H} and 19F{1H} NMR, and mass spectrometry. The antiproliferative effect of the new fluoroquinolone‐boron complexes in breast cancer (BC) derived cell lines MCF‐7 and SKBR‐3 was investigated. Compounds 9 b and 9 a showed antiproliferative in MCF‐7 cells, and 9 b, 11 b, 9 a, 7 a, 7b and 8 a showed similar effects in SKBR‐3 cells. Derivatives with p‐methoxybenzyl amino moieties at C‐7 and an ethyl or methyl group at N‐1 in the fluoroquinolone ring (9 a and 9 b) were the more efficient in both breast cancer cell lines. In addition, an 8‐nitro group to the fluoroquinolone (11 b) improved activity against SKBR‐3 cell proliferation. These compounds represent potential drug candidates for breast cancer treatment.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Hernández‐López,

Tejada‐Rodríguez,

Leyva‐Ramos

et al. 2023

ChemistrySelect

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“…The reaction is quantitative, regioselective, thermodynamic and kinetically favorable. On preliminary results, the ethyl 7‐azide‐1‐ethyl‐6,8‐difluoroquinolone‐3‐carboxylate 1 , and ethyl 7‐azide‐1‐ethyl‐6‐fluoroquinolone‐3‐carboxylate 2 were prepared from 2,3,4‐trifluoro‐, or 3,4‐difluoro‐aniline, according to the literature method . Azide fluoroquinolone 1 , was first synthesized and used for the CuAAC by CuI and NaOH (0.5 N) .…”

Section: Resultsmentioning

confidence: 99%

Copper(I)‐Catalyzed Azide‐Alkyne Cycloaddition Microwave‐Assisted: Preparation of 7‐(4‐Substituted‐1H‐1,2,3‐Triazol‐1‐yl)‐Fluoroquinolones

et al. 2019

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Nowadays, the pharmaceutical industry faces the challenge of innovating and increasing the productivity of new medicines due to the increasing multidrug resistance among bacteria, viruses and fungi. The main objective of the present study is connected quinolone and triazole molecules to enhance and broad antibacterial spectrum as well as to have multiple mechanisms of action. Preparation of 4‐substituted‐1H‐1,2,3‐triazol‐1‐yl in C‐7 of 6‐fluoro‐ and 6,8‐difluoro‐quinolone ring is showed. The synthesis involved the preparation of intermediate ethyl 7‐azide‐1‐ethyl‐fluoroquinolone‐3‐carboxylate, followed by copper(I)‐catalyzed azide‐alkyne cycloaddition to give 13 derivatives. The cycloaddition was carried out by two different methods, where it was observed that the microwave radiation was the best reaction condition, obtaining a range of yields of 47–93%, at 140 °C, 125Wmax for 10 minutes. Therefore, this methodology provided an easy pathway to synthesize a library of fluoroquinolones coupled to 1,2,3‐triazole, still unexplored.

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Ultrathin γ-Fe2O3 nanosheets as a highly efficient catalyst for the chemoselective hydrogenation of nitroaromatic compounds

Cui

Zhou

Dong

2018

Catalysis Communications

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An efficient reduction of azide to amine: a new methodology to synthesize ethyl 7-amino-1-ethyl-6,8-difluoroquinolone-3-carboxylate and its spectroscopic characterization

Cited by 3 publications

References 31 publications

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Copper(I)‐Catalyzed Azide‐Alkyne Cycloaddition Microwave‐Assisted: Preparation of 7‐(4‐Substituted‐1H‐1,2,3‐Triazol‐1‐yl)‐Fluoroquinolones

Ultrathin γ-Fe2O3 nanosheets as a highly efficient catalyst for the chemoselective hydrogenation of nitroaromatic compounds

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