Synthesis and Evaluation of the Antidepressant Activity of 5-Amine-Substituted 3-Bromo-1-(Thietan-3-yl)-4-Nitro-1H-Pyrazoles

5-Amino-substituted 3-bromo-1-(thietan-3-yl)-4-nitro-1 H -pyrazoles were synthesized by reacting 3,5-dibromo-1-(thietan-3-yl)-4-nitro-1 H -pyrazole with aliphatic, aromatic, and heterocyclic amines. The structures of the synthesized compounds were confirmed by IR, PMR, and 13 C NMR spectroscopy and...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2024-12, Vol.58 (8), p.1247-1253
Main Authors: Klen, E. E., Nikitina, I. L., Khaliullin, F. A., Shepilova, S. O., Nikitina, E. A., Gaisina, G. G., Samorodov, A. V., Pavlov, V. N.
Format: Article
Language:English
Subjects:
Medicine
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
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Summary:5-Amino-substituted 3-bromo-1-(thietan-3-yl)-4-nitro-1 H -pyrazoles were synthesized by reacting 3,5-dibromo-1-(thietan-3-yl)-4-nitro-1 H -pyrazole with aliphatic, aromatic, and heterocyclic amines. The structures of the synthesized compounds were confirmed by IR, PMR, and 13 C NMR spectroscopy and GC-MS data. According to in silico calculations, they were predicted to have no toxic risks (mutagenicity, tumorigenicity, reproductive effects, irritating effects), low toxicity (class IV-V), and acceptable oral bioavailability. The compounds exhibited varying degrees of antidepressant activity after a single intraperitoneal administration to male mice. The most significant effects were typical of 5-piperazinopyrazoles IIh and IIg , while IIh exhibited psychosedative properties and IIg had a psychoactivating effect.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-024-03265-0