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

被引:0
|
作者
Gonec, Tomas [1 ]
Stranik, Josef [1 ]
Pesko, Matus [2 ]
Kos, Jiri [1 ]
Oravec, Michal [3 ]
Kralova, Katarina [4 ]
Jampilek, Josef [5 ]
机构
[1] Univ Vet & Pharmaceut Sci, Fac Pharm, Dept Chem Drugs, Palackeho 1, Brno 61242, Czech Republic
[2] Comenius Univ, Fac Nat Sci, Dept Environm Ecol, Mlynska Dolina Ch 2, Bratislava 84215, Slovakia
[3] Global Change Res Inst CAS, Belidla 986-4a, Brno 60300, Czech Republic
[4] Comenius Univ, Fac Nat Sci, Inst Chem, Mlynska Dolina Ch 2, Bratislava 84215, Slovakia
[5] Comenius Univ, Fac Pharm, Dept Pharmaceut Chem, Odbojarov 10, Bratislava 83232, Slovakia
来源
20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC) | 2016年
关键词
Alkylcarbamates; Hydroxynaphthalene-carboxamides; PET inhibition; Spinach chloroplasts; Structure-activity relationships; BIOLOGICAL-ACTIVITY SPECTRUM; HERBICIDAL ACTIVITY; ELECTRON-TRANSPORT; SUBSTITUTED BENZANILIDES; ANTIBACTERIAL; SALICYLANILIDES; CHLOROPLASTS; UNCOUPLERS; ACIDS;
D O I
10.3390/ecsoc-20-b004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, a series of eight 1-[(2-nitrophenyl) carbamoyl] naphthalen-2-yl alkylcarbamates was prepared and characterized. The discussed compounds were prepared by microwave-assisted and conventional synthesis. The compounds were tested for their activity related to 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 0.233 to 0.487 mmol/L and the highest activity within the series of compounds was observed for 1-[(2-nitrophenyl) carbamoyl] naphthalen-2-yl pentylcarbamate. The compounds were found to inhibit PET in photosystem II.
引用
收藏
页数:10
相关论文
共 50 条
  • [21] 1-[(3-Methylpiperidin-1-yl)(3-nitrophenyl)methyl]naphthalen-2-ol
    Chen, Jin Mei
    Zhao, Hong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O3118 - U154
  • [22] (E)-1-(2,4-Dinitrophenyl)-2-[1-(2-nitrophenyl)ethylidene]hydrazine
    Nilwanna, Boonlerd
    Chantrapromma, Suchada
    Jansrisewangwong, Patcharaporn
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3084 - U1845
  • [23] 1-{2-[(E)-2-(2-Nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethanone
    Karthikeyan, S.
    Sethusankar, K.
    Saravanan, Velu
    Mohanakrishnan, Arasambattu K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1422 - +
  • [24] CHARACTERIZATION OF NEW PHOTOSYNTHESIS-INHIBITING IMIDAZOLIDINE DERIVATIVES .2. INTERPRETATION OF PREEMERGENCE HERBICIDAL PERFORMANCE FROM PHOTOSYNTHESIS-INHIBITING ACTIVITY AND SOIL ADSORPTION COEFFICIENT
    CHIBA, M
    YANASE, D
    ANDOH, A
    GOTOH, T
    PESTICIDE SCIENCE, 1995, 43 (04): : 287 - &
  • [25] N-[3-(2-nitrophenyl)allylidene]naphthalen-1-amine
    Yang, Xiao-Yan
    He, Xiao-Lian
    Li, Ying
    Bi, Sai
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O2919 - U2608
  • [26] Preparation and Photosynthesis-Inhibiting Activity of N-(n-Alkoxy)phenylamides of 2-Hydroxynaphthalene-1-carboxylic acid
    Gonec, Tomas
    Kos, Jiri
    Soral, Michal
    Pesko, Matus
    Oravec, Michal
    Liptaj, Tibor
    Kralova, Katarina
    Jampilek, Josef
    18TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY, 2014,
  • [27] (1-(4-(Naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine: A Wingless β-Catenin Agonist That Increases Bone Formation Rate
    Pelletier, Jeffrey C.
    Lundquist, Joseph T., IV
    Gilbert, Adam M.
    Alon, Nipa
    Bex, Frederick J.
    Bhat, Bheem M.
    Bursavich, Mattew G.
    Coleburn, Valerie E.
    Felix, Luciana A.
    Green, Daniel M.
    Green, Paula
    Hauze, Diane B.
    Kharode, Yogendra P.
    Lam, Ho-Sun
    Lockhead, Susan R.
    Magolda, Ronald L.
    Matteo, Jeanne J.
    Mehlmann, John F.
    Milligan, Colleen
    Murrills, Richard J.
    Pirrello, Jennifer
    Selim, Sally
    Sharp, Michael C.
    Unwalla, Ray J.
    Vera, Matthew D.
    Wrobel, Jay E.
    Yaworsky, Paul
    Bodine, Peter V. N.
    JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (22) : 6962 - 6965
  • [28] Investigating biological activity spectrum for novel quinoline analogues 2: Hydroxyquinolinecarboxamides with photosynthesis-inhibiting activity
    Musiol, Robert
    Tabak, Dominik
    Niedbala, Halina
    Podeszwa, Barbara
    Jampilek, Josef
    Kralova, Katarina
    Dohnal, Jiri
    Finster, Jacek
    Mencel, Agnieszka
    Polanski, Jaroslaw
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (08) : 4490 - 4499
  • [29] Crystal structure of 3-[4-(1-methylethyl)phenyl]-1-(naphthalen-2-yl)prop-2-en-1-one
    Assia, Sid
    Amel, Messai
    Nouara, Ziani
    Mahieddine, Mokhtari
    Kaddour, Lamara
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O1009 - +
  • [30] 1-(4-Chlorobutanoyl)-3-(2-nitrophenyl)-thiourea
    Ngah, Nurziana
    Kadir, Maisara
    Yamin, Bohari M.
    Yusof, M. Sukeri M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1801 - +