Synthesis, Antihelminthic and Insecticidal Activity of 2-[3-Methyl-6-Methoxy-7-(n-Propoxy)-3,4-Dihydroisoquinolin-1]Ethanoic Acid Amides

被引:0
|
作者
O. V. Surikova
A. G. Mikhailovskii
B. Ya. Syropyatov
A. S. Yusov
Yu. D. Khudyakova
机构
[1] Perm State Pharmaceutical Academy,
来源
关键词
cyclocondensation of O-; -propylated eugenol with cyanoacetamides; 2-[3-methyl-6-methoxy-7-(; -propoxy)-3,4-dihydroisoquinolin-1]ethanoic acid amide hydrochlorides; antihelminthic activity greater than that of Pyrantel; insecticidal activity comparable with that of diazinon and pirimiphos;
D O I
暂无
中图分类号
学科分类号
摘要
Cyclocondensation of O-n-propylated eugenol with cyanoacetamides was used to synthesize 2-[3-methyl-6-methoxy-7-(n-propoxy)-3,4-dihydroisoquinolin-1]ethanoic acid amides. The hydrochlorides of these compounds were tested for antihelminthic and insecticidal activity. The most active compounds were amides containing a cyclic amine fragment (pyrrolidine, piperidine, morpholine), which had greater activity than Pyrantel. Compounds without substituents at the amide nitrogen and the N-ethylamide had insecticidal activity at the levels of diazinon and pirimiphos.
引用
收藏
页码:22 / 25
页数:3
相关论文
共 50 条
  • [21] Synthesis of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)acetohydrazides via the Ritter reaction
    Alexander G. Mikhailovskii
    Evgeniya S. Pogorelova
    Nataliya N. Pershina
    Chemistry of Heterocyclic Compounds, 2020, 56 : 562 - 565
  • [22] Synthesis and Analgesic Activity of 2-(3,3-Dimethyl-3,4-Dihydroisoquinolin-1-yl)-2-(2-Arylhydrazono)-N-(2,4-Xylyl)-Acetamides
    Mikhailovskii, A. G.
    Yusov, A. S.
    Chashchina, S. V.
    Pershina, N. N.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2024, 58 (07) : 1050 - 1053
  • [23] Synthesis and biological activity of methyl N-methoxy-N-[2-(1,6-dihydro-1-substituent-6-oxo-pyridazin-3-yloxymethyl)phenl]carbamates
    Liu, WD
    Li, ZW
    Li, ZY
    Wang, XG
    Gao, BD
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (04) : 445 - 448
  • [24] Versatile synthesis of 3,4-dihydroisoquinolin-1(2H)-one derivatives via intra-molecular Friedel-Crafts reaction with trifluoromethanesulfonic acid
    Murashige, Ryo
    Ohtsuka, Yoko
    Sagisawa, Kazuki
    Shiraishi, Mitsuru
    TETRAHEDRON LETTERS, 2015, 56 (23) : 3410 - 3412
  • [25] Metal-free visible-light-catalyzed synthesis of 3-methyl-3,4-dihydroisoquinolin-1(2H)-one: mechanism, DFT calculation and optical properties
    Shuai Zou
    Li Pan
    Tian Xue
    Huang Huang
    Shu Geng
    Jun-Jie Ding
    Fei-Yan Fu
    Feng Huang
    Chemical Papers, 2021, 75 : 4069 - 4074
  • [26] SYNTHESIS AND INSECTICIDAL ACTIVITY OF LIGNAN ANALOGS .7. INSECTICIDAL ACTIVITY OF SESQUILIGNANS WITH A 3-ARYL-6-METHOXY-2-METHOXYMETHYL-1,4-BENZODIOXANYL GROUP
    YAMAUCHI, S
    ISHIBASHI, F
    TANIGUCHI, E
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (11) : 1760 - 1768
  • [27] Metal-free visible-light-catalyzed synthesis of 3-methyl-3,4-dihydroisoquinolin-1(2H)-one: mechanism, DFT calculation and optical properties
    Zou, Shuai
    Pan, Li
    Xue, Tian
    Huang, Huang
    Geng, Shu
    Ding, Jun-Jie
    Fu, Fei-Yan
    Huang, Feng
    CHEMICAL PAPERS, 2021, 75 (08): : 4069 - 4074
  • [28] Synthesis and Antiarrhythmic, Hemostatic, Anthelmintic, and Larvicidal Activity of (3,3-Dialkyl-6,7-Diethoxy-3,4-Dihydroisoquinolin-1(2H)-Ylidene)Acetamide Hydrochlorides
    A. G. Mikhailovskii
    E. S. Likhtenshtein
    I. P. Rudakova
    A. V. Starkova
    N. N. Pershina
    Pharmaceutical Chemistry Journal, 2021, 55 : 638 - 643
  • [29] Synthesis and Analgesic, Antihypoxic, and Antimicrobial Activity of (Z)-2-(2-Arylhydrazono)-2-(3,3-Dimethyl-3,4-Dihydroisoquinolin-1-Yl)Acetamides
    A. G. Mikhailovskii
    E. S. Pogorelova
    N. N. Pershina
    R. R. Makhmudov
    V. V. Novikova
    Pharmaceutical Chemistry Journal, 2020, 53 : 1013 - 1017
  • [30] Synthesis and Analgesic, Antihypoxic, and Antimicrobial Activity of (Z)-2-(2-Arylhydrazono)-2-(3,3-Dimethyl-3,4-Dihydroisoquinolin-1-Yl)Acetamides
    Mikhailovskii, A. G.
    Pogorelova, E. S.
    Pershina, N. N.
    Makhmudov, R. R.
    Novikova, V. V.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2020, 53 (11) : 1013 - 1017