Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: IX. N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl) Ureas and Thioureas

被引:2
|
作者
Kuznetsov, Ya P. [1 ]
Degtyarenko, E. K. [1 ]
Burmistrov, V. V. [1 ]
Saeef, M. H. Abbas [1 ]
Pitushkin, D. A. [2 ]
Vernigora, A. A. [1 ]
Butov, G. M. [2 ]
机构
[1] Volgograd State Tech Univ, Volgograd 400005, Russia
[2] Volgograd State Tech Univ, Volzhsky Polytech Inst Branch, Volzhsky 404121, Russia
基金
俄罗斯基础研究基金会;
关键词
natural compounds; bicyclo[2; 2; 1]heptane; isocyanate; isothiocyanate; urea; halogen-containing aromatic isocyanates; soluble epoxide hydrolase; optical isomerism; racemate; DERIVATIVES; INHIBITOR;
D O I
10.1134/S1070428021040035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N '-Disubstituted ureas and thioureas containing a lipophilic optically active natural bicyclic moiety have been synthesized by reactions of (R)-, (S)-, and (RS)-1,1,7-trimethylbicyclo[2.2.1]heptan-2-amines with aromatic isocyanates and isothiocyanates in up to 85% and 88% yield, respectively, with the goal of estimating enantiomeric stereospecificity of human soluble epoxide hydrolase (hsEH). The synthesized com-pounds are promising as inhibitors of RNA viruses and hsEH.
引用
收藏
页码:515 / 523
页数:9
相关论文
共 50 条
  • [1] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: IX. N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl) Ureas and Thioureas
    Ya. P. Kuznetsov
    E. K. Degtyarenko
    V. V. Burmistrov
    M. H. Abbas Saeef
    D. A. Pitushkin
    A. A. Vernigora
    G. M. Butov
    [J]. Russian Journal of Organic Chemistry, 2021, 57 : 515 - 523
  • [2] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XIX. exo-Isomers of N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl)-N′-R-ureas and -thioureas
    Burmistrov, V. V.
    Kuznetsov, Ya. P.
    Novikov, V. V.
    Abbas, M. H. Saeef
    Davidenko, A. V.
    Vernigora, A. A.
    Butov, G. M.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (03) : 403 - 409
  • [3] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XII. N-(1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl)-N′-R-ureas and -thioureas
    Ya. P. Kuznetsov
    A. A. Vernigora
    E. K. Degtyarenko
    M. H. Abbas Saeef
    D. A. Pitushkin
    V. V. Burmistrov
    G. M. Butov
    [J]. Russian Journal of Organic Chemistry, 2021, 57 : 1891 - 1900
  • [4] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XII. N-(1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl)-N′-R-ureas and -thioureas
    Kuznetsov, Ya P.
    Vernigora, A. A.
    Degtyarenko, E. K.
    Saeef, M. H. Abbas
    Pitushkin, D. A.
    Burmistrov, V. V.
    Butov, G. M.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (12) : 1891 - 1900
  • [5] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XVIII. N-[2-(Adamantan-2-yl)ethyl]-N′-R-ureas and -Thioureas
    Burmistrov, V. V.
    Zapravdina, D. M.
    Savelyev, E. N.
    Orlinson, B. S.
    Butov, G. M.
    Novakov, I. A.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (01) : 12 - 17
  • [6] Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: V. 1-(Bicyclo[2.2.1]heptan-2-yl)-3-R- and 1-(1,7,7-Tricyclo[2.2.1]heptan-2-yl)-3-R-ureas
    D. A. Pitushkin
    V. V. Burmistrov
    M. H. Abbas Saeef
    A. A. Vernigora
    G. M. Butov
    [J]. Russian Journal of Organic Chemistry, 2020, 56 : 1893 - 1904
  • [7] Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: V. 1-(Bicyclo[2.2.1]heptan-2-yl)-3-R- and 1-(1,7,7-Tricyclo[2.2.1]heptan-2-yl)-3-R-ureas
    Pitushkin, D. A.
    Burmistrov, V. V.
    Saeef, M. H. Abbas
    Vernigora, A. A.
    Butov, G. M.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (11) : 1893 - 1904
  • [8] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VI. N-[Fluoro(chloro)phenyl]-N′-(4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptan-1-yl)ureas
    Pitushkin, D. A.
    Burmistrov, V. V.
    Kuznetsov, Ya. P.
    Ivankina, O. M.
    Butov, G. M.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (12) : 2057 - 2066
  • [9] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VI. N-[Fluoro(chloro)phenyl]-N′-(4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptan-1-yl)ureas
    D. A. Pitushkin
    V. V. Burmistrov
    Ya. P. Kuznetsov
    O. M. Ivankina
    G. M. Butov
    [J]. Russian Journal of Organic Chemistry, 2020, 56 : 2057 - 2066
  • [10] Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: II. N-(4-Oxoadamantan-1-yl)-N′-[fluoro(chloro)phenyl]ureas
    D. V. Danilov
    V. V. Burmistrov
    E. V. Rasskazova
    G. M. Butov
    [J]. Russian Journal of Organic Chemistry, 2020, 56 : 983 - 989