2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Anticonvulsant Activity
3. Materials and Methods
3.1. General Information
3.2. Synthesis of 2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide (3)
- White crystals (80%). 1H-NMR (300 MHz, DMSO-d6) δ: 0.65 (s, 3H, CH3), 0.82 (s, 6H, 2CH3), 0.86 (s, 3H, CH3), 0.90 (s, 3H, CH3), 1.21 (m, 8H, 2CH2-CH2), 1.46‒1.51 (m, 2H, CH2), 1.65 (t, 1H, CH), 1.77 (m, 1H, CH), 1.89 (m, 2H, CH2), 2.30 (m, 1H, CH), 9.51 (s, 1H, NH). 13C-NMR (100 MHz, DMSO-d6) δ: 177.4 (C=O), 171.3 (C-2), 52.3 (C-1), 47.8 (C-7), 47.6 (C-4), 43.9 (CH), 35.1 (C-3), 34.5 (CH2), 32.7 (C-6), 27.3 (C-5), 20.5 (CH2), 18.8 (C-8,9), 14.2 (C-10), 11.5 (CH3). FT-IR (νmax, CM−1): 3179 (N-H), 2970‒2834 (C-H), 1697 (C=O). Raman (νmax, CM−1): 2943‒2872 (C-H), 1646 (C=N). MS (FAB) m/z: 293 [M + H]+. HPLC: tr = 23.43 min. M.p. (DSC) onset: 154.26 °C, peak max: 155.46 °C (Supplementary Materials).
3.3. Anticonvulsant Screening
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Compound | Control | Camphor | VPA | Compound 3 |
---|---|---|---|---|
3 h after single oral administration | ||||
% Mortality protection | 0 | 60 | 80 | 80 |
24 h after single oral administration | ||||
% Mortality protection | 0 | 20 | 60 | 100 |
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Nesterkina, M.; Barbalat, D.; Rakipov, I.; Kravchenko, I. 2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide. Molbank 2020, 2020, M1164. https://doi.org/10.3390/M1164
Nesterkina M, Barbalat D, Rakipov I, Kravchenko I. 2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide. Molbank. 2020; 2020(4):M1164. https://doi.org/10.3390/M1164
Chicago/Turabian StyleNesterkina, Mariia, Dmytro Barbalat, Ildar Rakipov, and Iryna Kravchenko. 2020. "2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide" Molbank 2020, no. 4: M1164. https://doi.org/10.3390/M1164