The new compound (2-chloroethoxy-4′-dimethylaminophenyl)phosphorylacetic acid N-acetylhydrazide (II) was synthesized. Compound II was proposed as a metabolite of (2-chloroethoxy-4′-dimethylaminophenyl)phosphorylacetic acid hydrazide (CAPAH, I), a drug possessing nootropic activity. The psychotropic and antiarrhythmic properties of II were compared with those of I. It was established that II did not possess nootropic and antidepressant activities although its antiarrhythmic properties were more pronounced. It was suggested that the C(O)CH3 fragment, being a substituent on the hydrazide in II, decreased penetration of the compound through the blood―brain barrier, which could explain the absence of psychotropic activity.
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References
I. I. Semina, N. A. Tikhonova, A. Z. Baichurina, et al., Vestn. Ross. Akad. Med. Nauk, No. 3, 32-36 (1999).
I. I. Semina, E. V. Shilovskaya, R. I. Tarasova, et al., Khim.-farm. Zh., 36, No. 4, 3-6 (2002).
R. I. Tarasova, O. V. Voskresenskaya, I. I. Semina, et al., Khim.-farm. Zh., 36, No. 6, 17-20 (2002).
G. G. Nikolaeva, Author's Abstract of a Candidate Dissertation in Medical Sciences, Kazan (1998).
R. I. Tarasova, N. A. Blyukherova, O. M. Kalina, G. F. Rzhevskaya, RF Pat. No. 2,062,099 (1992); Byull. Izobret., No. 17 (1996).
R. I. Tarasova, I. I. Semina, V. A. Pavlov, V. V. Moskva, RF Pat. No. 2,141,961 (1999); Byull. Izobret., No. 33 (2000).
D. Yu. Rusakov, A. V. Valʹdman, Farmakol. Toksikol., 46, No. 5, 107–111 (1983).
N. V. Kaverina, Z. P. Senova, Methodical Recommendations for Experimental (Preclinical) Study of Drugs Proposed for Clinical Trials as Agents for Prevention and Treatment of Cardiac Rhythm Disruptions [in Russian], Meditsina, Moscow (1981), pp. 3–12.
V. V. Gorbunova, N. P. Gorbunov, Farmakol. Toksikol., No. 3, 48-50 (1983).
E. I. Gendenshtein, Ya. V. Kostin, N. N. Markelova, et al., Farmakol. Toksikol., 53, No. 4, 28-30 (1990).
E. I. Gendenshtein, S. M. Lemkina, L. N. Sernov, Farmakol. Toksikol., No. 6, 83-86 (1985).
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The work was sponsored by NIOKR-RFFI [R&D RFBR] (Grant 03-04-96272).
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Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 47, No. 1, pp. 29-31, January, 2013.
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Semina, I.I., Balashov, V.P., Kurmysheva, T.V. et al. Synthesis and pharmacological activity of (2-chloroethoxy-4′-dimethylaminophenyl)phosphorylacetic acid hydrazide (CAPAH) and its metabolite (N-acetyl derivative). Pharm Chem J 47, 28–30 (2013). https://doi.org/10.1007/s11094-013-0889-2
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DOI: https://doi.org/10.1007/s11094-013-0889-2