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Synthesis of 3,3-Dimethyl- and 3,3-Diethyl-Substituted 2-(3,4-Dihydroisoquinolin-1-yl)Carboxylic Acid Amide Hydrochlorides and Their Anti-Arrhythmic, Hemostatic, Anthelmintic, and Larvicidal Activity

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Pharmaceutical Chemistry Journal Aims and scope

Series of 3,3-dimethyl- and 3,3-diethyl-substituted 2-R-(3,4-dihydroisoquinolin-1-yl)acetamides were synthesized via Ritter reactions of 1-(3,4-dimethoxyphenyl)-2-methylpropanol-2 and 1-phenyl-2-ethylbutanol-2 with 2-R-cyanoacetamides (R = Et, n-Pr, i-Pr, n-Bu, n-Am, and i-Am). The hydrochlorides of the obtained compounds were tested for anti-arrhythmic activity using the CaCl2 model. Three of ten compounds showed anti-arrhythmic activity with a maximum anti-arrhythmic index (AI) of 3.9.With respect to blood clotting, all compounds proved to be hemostatics. The most active compound increased the blood coagulation index up to 37.9%. Eight compounds exceeded pyrantel and two compounds exceeded levamisole with respect to anthelmintic activity. Larvicidal (insecticidal) effects were observed for nine compounds, two of which reduced the larvae life span to 10.6 and 10.4 min, thus exceeding the effect of diazinon (17.0 min).

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, 2 Polevaya St., Perm, 614990, Russia

    D. A. Peretyagin, A. G. Mikhailovskii, I. P. Rudakova & A. V. Starkova

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  1. D. A. Peretyagin
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  2. A. G. Mikhailovskii
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  3. I. P. Rudakova
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  4. A. V. Starkova
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Correspondence to A. G. Mikhailovskii.

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 56, No. 6, pp. 23 – 28, June, 2022.

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Peretyagin, D.A., Mikhailovskii, A.G., Rudakova, I.P. et al. Synthesis of 3,3-Dimethyl- and 3,3-Diethyl-Substituted 2-(3,4-Dihydroisoquinolin-1-yl)Carboxylic Acid Amide Hydrochlorides and Their Anti-Arrhythmic, Hemostatic, Anthelmintic, and Larvicidal Activity. Pharm Chem J 56, 748–753 (2022). https://doi.org/10.1007/s11094-022-02705-z

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  • DOI: https://doi.org/10.1007/s11094-022-02705-z

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