About: Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates     Goto   Sponge   Distinct   Permalink

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  • A series of twenty substituted 2-hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(alkoxycarbonyl)amino]benzoates were prepared and characterized. As similar compounds have been described as potential antimycobacterials, primary in vitro screening of the synthesized carbamates was also performed against two mycobacterial species. 2-Hydroxy-3-[2-(2,6-dimethoxyphenoxy) ethylamino]propyl 4-(butoxycarbonylamino)benzoate hydrochloride, 2-hydroxy-3-[2-(4-methoxyphenoxy)ethylamino]-propyl 4-(butoxycarbonylamino)benzoate hydrochloride, and 2-hydroxy-3-[ 2-(2-methoxyphenoxy)ethylamino]-propyl 4-(butoxycarbonylamino)benzoate hydrochloride showed higher activity against M. avium subsp. paratuberculosis and M. intracellulare than the standards ciprofloxacin, isoniazid, or pyrazinamide. Cytotoxicity assay of effective compounds was performed using the human monocytic leukaemia THP-1 cell line. Compounds with predicted amphiphilic properties were also tested for their effects on the rate of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. All butyl derivatives significantly stimulated the rate of PET, indicating that the compounds can induce conformational changes in thylakoid membranes resulting in an increase of their permeability and so causing uncoupling of phosphorylation from electron transport.
  • A series of twenty substituted 2-hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(alkoxycarbonyl)amino]benzoates were prepared and characterized. As similar compounds have been described as potential antimycobacterials, primary in vitro screening of the synthesized carbamates was also performed against two mycobacterial species. 2-Hydroxy-3-[2-(2,6-dimethoxyphenoxy) ethylamino]propyl 4-(butoxycarbonylamino)benzoate hydrochloride, 2-hydroxy-3-[2-(4-methoxyphenoxy)ethylamino]-propyl 4-(butoxycarbonylamino)benzoate hydrochloride, and 2-hydroxy-3-[ 2-(2-methoxyphenoxy)ethylamino]-propyl 4-(butoxycarbonylamino)benzoate hydrochloride showed higher activity against M. avium subsp. paratuberculosis and M. intracellulare than the standards ciprofloxacin, isoniazid, or pyrazinamide. Cytotoxicity assay of effective compounds was performed using the human monocytic leukaemia THP-1 cell line. Compounds with predicted amphiphilic properties were also tested for their effects on the rate of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. All butyl derivatives significantly stimulated the rate of PET, indicating that the compounds can induce conformational changes in thylakoid membranes resulting in an increase of their permeability and so causing uncoupling of phosphorylation from electron transport. (en)
Title
  • Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates
  • Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates (en)
skos:prefLabel
  • Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates
  • Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates (en)
skos:notation
  • RIV/62157124:16370/13:43872240!RIV14-MSM-16370___
http://linked.open...avai/predkladatel
http://linked.open...avai/riv/aktivita
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  • S
http://linked.open...iv/cisloPeriodika
  • 2013
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
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  • 109464
http://linked.open...ai/riv/idVysledku
  • RIV/62157124:16370/13:43872240
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • POTENTIAL ANTITUBERCULOTICS; LOCAL-ANESTHETICS; QUATERNARY AMMONIUM-SALTS; SUBSTITUTED PHENYLCARBAMIC ACIDS; PHOTOSYNTHETIC ELECTRON-TRANSPORT; DIPALMITOYLPHOSPHATIDYLCHOLINE MODEL MEMBRANE (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV
  • [D2C6297EF149]
http://linked.open...i/riv/nazevZdroje
  • Scientific World Journal
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • neuveden
http://linked.open...iv/tvurceVysledku
  • Jampílek, Josef
  • Kollár, Peter
  • Mokrý, Petr
  • Peško, Matúš
  • Coffey, Aidan
  • Keltošová, Stanislava
  • Govender, Rodney
  • O'Mahony, Jim
  • Tengler, Jan
  • Kral'ova, Katarína
  • Kapustíková, Iva
http://linked.open...ain/vavai/riv/wos
  • 000326829200001
issn
  • 1537-744X
number of pages
http://bibframe.org/vocab/doi
  • 10.1155/2013/274570
http://localhost/t...ganizacniJednotka
  • 16370
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