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Molecules 2014, 19(4), 4745-4759; doi:10.3390/molecules19044745
Article

Pharmacological and Structure-Activity Relationship Evaluation of 4-aryl-1-Diphenylacetyl(thio)semicarbazides

1,* , 2
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1
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1
,
3
,
1,4
,
2
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1 Department of Organic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland 2 Department of Pharmacology and Pharmacodynamics, Medical University, Chodźki 4a, 20-093 Lublin, Poland 3 History of Medical Sciences Department, Medical University, Szkolna 18, 20-124 Lublin, Poland 4 Institute of Applied Radiation Chemistry, Technical University of Lodz, Zeromskiego 116, 90-924 Lodz, Poland
* Author to whom correspondence should be addressed.
Received: 7 February 2014 / Revised: 27 March 2014 / Accepted: 3 April 2014 / Published: 16 April 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

This article describes the synthesis of six 4-aryl-(thio)semicarbazides (series a and b) linked with diphenylacetyl moiety along with their pharmacological evaluation on the central nervous system in mice and computational studies, including conformational analysis and electrostatic properties. All thiosemicarbazides (series b) were found to exhibit strong antinociceptive activity in the behavioural model. Among them, compound 1-diphenylacetyl-4-(4-methylphenyl)thiosemicarbazide 1b was found to be the most potent analgesic agent, whose activity is connected with the opioid system. For compounds from series a significant anti-serotonergic effect, especially for compound 1-diphenylacetyl-4-(4-methoxyphenyl)semicarbazide 2b was observed. The computational studies strongly support the obtained results.
Keywords: (thio)semicarbazides; conformational analysis; electrostatic properties; CNS activity; analgesic activity; serotonergic activity (thio)semicarbazides; conformational analysis; electrostatic properties; CNS activity; analgesic activity; serotonergic activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Wujec, M.; Kędzierska, E.; Kuśmierz, E.; Plech, T.; Wróbel, A.; Paneth, A.; Orzelska, J.; Fidecka, S.; Paneth, P. Pharmacological and Structure-Activity Relationship Evaluation of 4-aryl-1-Diphenylacetyl(thio)semicarbazides. Molecules 2014, 19, 4745-4759.

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