Synthesis of 5-Arylisoxazole and 4,5-Dichloroisothiazole Amino-Substituted Derivatives and Their Biological Activity

被引:1
|
作者
Kolesnik, I. A. [1 ]
Petkevich, S. K. [1 ]
Mertsalov, D. F. [2 ]
Chervyakova, L., V [2 ]
Nadirova, M. A. [2 ]
Tyurin, A. P. [3 ]
Guan, A. Y. [4 ]
Liu, C. L. [4 ]
Potkin, V., I [1 ]
机构
[1] Natl Acad Sci Belarus, Inst Phys & Organ Chem, Minsk 220072, BELARUS
[2] Peoples Friendship Univ Russia, Moscow 117198, Russia
[3] Gause Inst New Antibiot, Moscow 119021, Russia
[4] Shenyang Sinochem Agrochem R&D Co Ltd, State Key Lab Discovery & Dev Novel Pesticide, Shenyang 110021, Peoples R China
基金
俄罗斯基础研究基金会;
关键词
isoxazole; isothiazole; amine; alkylation; acylation; phthalimide; ISOXAZOLE; AMIDES;
D O I
10.1134/S1070363222010066
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of amino derivatives of 5-arylisoxazoles and 4,5-dichloroisothiazole with primary and secondary amino groups was synthesized. 3-Aminomethyl-5-arylisoxazol-3-ylmethanamines were obtained on the basis of 5-aryl-3-(chloromethyl)isoxazoles using the Gabriel phthalimide method. 5-Arylisoxazol-3-yl- and 4,5-dichloroisothiazol-3-ylallylamines were synthesized in two ways: reduction of azomethines obtained by condensation of 5-arylisoxazolyl- and 4,5-dichloroisothiazolyl-3-carbaldehydes with allylamine, and by nucleophilic substitution of the chlorine atom in 3-chloromethyl derivatives of the corresponding azoles by reaction with allylamine. Amides and sulfonamides of azolylallylamines were synthesized. Some of the compounds obtained showed antibacterial and fungicidal activity.
引用
收藏
页码:29 / 39
页数:11
相关论文
共 50 条
  • [11] Esters of benzoic, 5-arylisoxazole-3-carboxylic and 4,5-dichloroisothiazole-3-carboxylic acids
    E. A. Dikusar
    V. I. Potkin
    N. A. Zhukovskaya
    M. Yu. Murashova
    S. K. Petkevich
    A. V. Kletskov
    R. M. Zolotar’
    O. P. Chepik
    Russian Journal of General Chemistry, 2014, 84 : 1179 - 1185
  • [12] 5-Amino-Substituted Derivatives of 4-Nitrofurazane: Synthesis, Structure, and Biological Activity
    I. V. Galkina
    G. L. Takhautdinova
    K. A. Ivshin
    Kh. R. Khayarov
    D. R. Islamov
    Yu. V. Bakhtiyarova
    L. N. Yamalieva
    O. N. Kataeva
    V. I. Galkin
    Russian Journal of General Chemistry, 2018, 88 : 898 - 902
  • [13] 5-Amino-Substituted Derivatives of 4-Nitrofurazane: Synthesis, Structure, and Biological Activity
    Galkina, I. V.
    Takhautdinova, G. L.
    Ivshin, K. A.
    Khayarov, Kh. R.
    Islamov, D. R.
    Bakhtiyarova, Yu. V.
    Yamalieva, L. N.
    Kataeva, O. N.
    Galkin, V. I.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (05) : 898 - 902
  • [14] Esters of benzoic, 5-arylisoxazole-3-carboxylic and 4,5-dichloroisothiazole-3-carboxylic acids
    Dikusar, E. A.
    Potkin, V. I.
    Zhukovskaya, N. A.
    Murashova, M. Yu
    Petkevich, S. K.
    Kletskov, A. V.
    Zolotar', R. M.
    Chepik, O. P.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (06) : 1179 - 1185
  • [15] Synthesis of 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carboxylates derived from natural alcohols, thymol, and its synthetic analogs
    S. K. Petkevich
    A. S. Kishkentaeva
    O. G. Ryazantsev
    E. A. Dikusar
    N. A. Zhukovskaya
    A. V. Kletskov
    N. G. Kozlov
    G. A. Atazhanova
    S. M. Adekenov
    V. I. Potkin
    S. G. Pashkevich
    A. A. Denisov
    V. A. Kul’chitskii
    Russian Journal of Organic Chemistry, 2014, 50 : 1351 - 1356
  • [16] Synthesis of 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carboxylates derived from natural alcohols, thymol, and its synthetic analogs
    Petkevich, S. K.
    Kishkentaeva, A. S.
    Ryazantsev, O. G.
    Dikusar, E. A.
    Zhukovskaya, N. A.
    Kletskov, A. V.
    Kozlov, N. G.
    Atazhanova, G. A.
    Adekenov, S. M.
    Potkin, V. I.
    Pashkevich, S. G.
    Denisov, A. A.
    Kul'chitskii, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (09) : 1351 - 1356
  • [17] Synthesis and Photovoltaic Performance of β-Amino-Substituted Porphyrin Derivatives
    Cerqueira, Ana F. R.
    Pinto, Ana Lucia
    Malta, Gabriela
    Neves, Maria G. P. M. S.
    Parola, A. Jorge
    Tome, Augusto C.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (11)
  • [18] Synthesis of new fungicidal biphenyl derivatives of 4,5-dichloroisothiazole-3-carboxylic acid
    D. A. Vasilevskii
    N. A. Galinovskii
    L. A. Golovchenko
    V. I. Potkin
    A. V. Kletskov
    V. K. Ol’khovik
    Russian Journal of Organic Chemistry, 2014, 50 : 1033 - 1038
  • [19] Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives
    Nematollahi, D
    Hesari, M
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2005, 577 (02) : 197 - 203
  • [20] Synthesis of 2-Chloro-4,6-Diamino-5-Cyanopyrimidine and Its Amino-substituted Derivatives
    Yu, HongMei
    Li, HaiFeng
    Jia, HongMin
    Zhu, XiuHui
    FUNDAMENTAL OF CHEMICAL ENGINEERING, PTS 1-3, 2011, 233-235 : 321 - 324