Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates

Eight 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates and eight 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibit...

Full description

Bibliographic Details
Main Authors: Tomas Gonec, Josef Stranik, Matus Pesko, Jiri Kos, Michal Oravec, Katarina Kralova, Josef Jampilek
Format: Article
Language:English
Published: MDPI AG 2017-07-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/22/7/1199
_version_ 1819070276849106944
author Tomas Gonec
Josef Stranik
Matus Pesko
Jiri Kos
Michal Oravec
Katarina Kralova
Josef Jampilek
author_facet Tomas Gonec
Josef Stranik
Matus Pesko
Jiri Kos
Michal Oravec
Katarina Kralova
Josef Jampilek
author_sort Tomas Gonec
collection DOAJ
description Eight 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates and eight 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity of the compounds was relatively low; the corresponding IC50 values ranged from 0.05 to 0.664 mmol/L; and the highest activity within the series of compounds was observed for 1-[(2-chlorophenyl)-carbamoyl]naphthalen-2-yl propylcarbamate. It has been proven that the compounds are PET-inhibitors in photosystem II. Despite rather low PET-inhibiting activities, primary structure-activity trends can be discussed.
first_indexed 2024-12-21T17:03:22Z
format Article
id doaj.art-b72c9130e5084d449085190efbe2ed87
institution Directory Open Access Journal
issn 1420-3049
language English
last_indexed 2024-12-21T17:03:22Z
publishDate 2017-07-01
publisher MDPI AG
record_format Article
series Molecules
spelling doaj.art-b72c9130e5084d449085190efbe2ed872022-12-21T18:56:35ZengMDPI AGMolecules1420-30492017-07-01227119910.3390/molecules22071199molecules22071199Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl AlkylcarbamatesTomas Gonec0Josef Stranik1Matus Pesko2Jiri Kos3Michal Oravec4Katarina Kralova5Josef Jampilek6Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech RepublicDepartment of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech RepublicDepartment of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, SlovakiaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, SlovakiaGlobal Change Research Institute CAS, Belidla 986/4a, 60300 Brno, Czech RepublicInstitute of Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, SlovakiaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, SlovakiaEight 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates and eight 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity of the compounds was relatively low; the corresponding IC50 values ranged from 0.05 to 0.664 mmol/L; and the highest activity within the series of compounds was observed for 1-[(2-chlorophenyl)-carbamoyl]naphthalen-2-yl propylcarbamate. It has been proven that the compounds are PET-inhibitors in photosystem II. Despite rather low PET-inhibiting activities, primary structure-activity trends can be discussed.https://www.mdpi.com/1420-3049/22/7/1199alkylcarbamateshydroxynaphthalene-carboxamidesPET inhibitionspinach chloroplastsstructure-activity relationships
spellingShingle Tomas Gonec
Josef Stranik
Matus Pesko
Jiri Kos
Michal Oravec
Katarina Kralova
Josef Jampilek
Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates
Molecules
alkylcarbamates
hydroxynaphthalene-carboxamides
PET inhibition
spinach chloroplasts
structure-activity relationships
title Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates
title_full Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates
title_fullStr Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates
title_full_unstemmed Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates
title_short Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates
title_sort photosynthesis inhibiting activity of 1 2 chlorophenyl carbamoyl and 1 2 nitrophenyl carbamoyl naphthalen 2 yl alkylcarbamates
topic alkylcarbamates
hydroxynaphthalene-carboxamides
PET inhibition
spinach chloroplasts
structure-activity relationships
url https://www.mdpi.com/1420-3049/22/7/1199
work_keys_str_mv AT tomasgonec photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates
AT josefstranik photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates
AT matuspesko photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates
AT jirikos photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates
AT michaloravec photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates
AT katarinakralova photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates
AT josefjampilek photosynthesisinhibitingactivityof12chlorophenylcarbamoyland12nitrophenylcarbamoylnaphthalen2ylalkylcarbamates