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：
Pharmaceutical Chemistry Journal | 2017年 / 51卷
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
  • [31] Synthesis and Antiarrhythmic, Hemostatic, Anthelmintic, and Larvicidal Activity of (3,3-Dialkyl-6,7-Diethoxy-3,4-Dihydroisoquinolin-1(2H)-Ylidene)Acetamide Hydrochlorides
    Mikhailovskii, A. G.
    Likhtenshtein, E. S.
    Rudakova, I. P.
    Starkova, A., V
    Pershina, N. N.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2021, 55 (07) : 638 - 643
  • [32] Optimization of Orally Bioavailable Enhancer of Zeste Homolog 2 (EZH2) Inhibitors Using Ligand and Property-Based Design Strategies: Identification of Development Candidate (R)-5,8-Dichloro-7-(methoxy(oxetan-3-yl)methyl)-2-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one (PF-06821497)
    Kung, Pei-Pei
    Bingham, Patrick
    Brooun, Alexei
    Collins, Michael
    Deng, Ya-Li
    Dinh, Dac
    Fan, Connie
    Gajiwala, Ketan S.
    Grantner, Rita
    Gukasyan, Hovhannes J.
    Hu, Wenyue
    Huang, Buwen
    Kania, Robert
    Kephart, Susan E.
    Krivacic, Cody
    Kumpf, Robert A.
    Khamphavong, Penney
    Kraus, Manfred
    Liu, Wei
    Maegley, Karen A.
    Nguyen, Lisa
    Ren, Shijian
    Richter, Dan
    Rollins, Robert A.
    Sach, Neal
    Sharma, Shikhar
    Sherrill, John
    Spangler, Jillian
    Stewart, Albert E.
    Sutton, Scott
    Uryu, Sean
    Verhelle, Dominique
    Wang, Hui
    Wang, Shuiwang
    Wythes, Martin
    Xin, Shuibo
    Yamazaki, Shinji
    Zhu, Huichun
    Zhu, JinJiang
    Zehnder, Luke
    Edwards, Martin
    JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (03) : 650 - 665
  • [33] THE CHEMISTRY OF PHTHALIDE-3-CARBOXYLIC ACID .6. THE STEREOCHEMISTRY OF SOME 3-AMINO(ARYL)METHYLPHTHALIDES AND THE DERIVED 3-ARYL-4-HYDROXY-3,4-DIHYDROISOQUINOLIN-1(2H)-ONES
    COLLINS, PR
    JANOWSKI, WK
    PRAGER, RH
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (04) : 549 - 559
  • [34] Synthesis, Anti-Arrhythmic, Hemostatic, Anthelmintic, and Larvicidal Activity of 2-(3-spiro-cycloalkyl-3,4-dihydroisoquinolin-1-yl)-Carboxylic Acid Amide Hydrochlorides
    Peretyagin, D. A.
    Mikhailovskii, A. G.
    Rudakova, I. P.
    Starkova, A., V
    Gashkova, O., V
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2022, 55 (12) : 1299 - 1303
  • [35] Synthesis, Anti-Arrhythmic, Hemostatic, Anthelmintic, and Larvicidal Activity of 2-(3-spiro-cycloalkyl-3,4-dihydroisoquinolin-1-yl)-Carboxylic Acid Amide Hydrochlorides
    D. A. Peretyagin
    A. G. Mikhailovskii
    I. P. Rudakova
    A. V. Starkova
    O. V. Gashkova
    Pharmaceutical Chemistry Journal, 2022, 55 : 1299 - 1303
  • [36] Synthesis and Biological Activity of 2-(3,3-Dimethyl-6,7-Diethoxy-3,4-Dihydroisoquinolin-1-yl)Carboxylic Acid Hydrochlorides and Their Benzo[f]-Analogs
    Peretyagin, D. A.
    Mikhailovskii, A. G.
    Rudakova, I. P.
    Starkova, A., V
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2022, 56 (08) : 1054 - 1059
  • [37] Synthesis and Biological Activity of 2-(3,3-Dimethyl-6,7-Diethoxy-3,4-Dihydroisoquinolin-1-yl)Carboxylic Acid Hydrochlorides and Their Benzo[f]-Analogs
    D. A. Peretyagin
    A. G. Mikhailovskii
    I. P. Rudakova
    A. V. Starkova
    Pharmaceutical Chemistry Journal, 2022, 56 : 1054 - 1059
  • [38] Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
    Bansode, Ajay H.
    Suryavanshi, Gurunath
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) : 1390 - 1400
  • [39] Enantioselective total synthesis of (2R,3R,6R)-N-methyl-6-(deca-1′,3′,5′-trienyl)-3-methoxy-2-methylpiperidine, an insecticidal alkaloid
    Nakatani, Y
    Oshita, J
    Ishigami, K
    Watanabe, H
    Kitahara, T
    TETRAHEDRON, 2006, 62 (01) : 160 - 165
  • [40] SYNTHESIS OF SOME 1-CHLOROPYRIDINOYL-2-METHYL-5-METHOXY-3-INDOLYLACETIC ACIDS AND PYRIDYLMETHYLAMIDES OF 1-(6-CHLORONICOTINOYL)-2-METHYL-5-METHOXY-3-INDOLYLACETIC ACID
    BINIECKI, S
    LEMPKE, T
    ROCZNIKI CHEMII, 1976, 50 (02): : 315 - 321
12345