Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide.
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFCG |
Texto Completo: | http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260 |
Resumo: | The synthesis of a monoterpene-based para-toluenesulfonamide is reported starting from naturally occurring (R)- (−)-carvone (1), by 1,2-addition of HCN followed by reduction with lithium aluminum hydride to afford the amino alcohols 3a and 3b. Tosylation of thismixture with p-toluenesulfonyl chloride furnished sulfonamide 4 in 55% overall yield. Compound 4 was evaluated in behavior animal models to investigate its effects on the central nervous system. It showed low toxicity and sedative action in mice, indicating it to be psychoactive. It also caused a decrease in the spontaneous motor activity of mice. This depressant effect was confirmed in the acetic acid-induced writhing test, which demonstrated a significant antinociceptive response more potent than 1. The present results provide evidence that sulfonamide 4 has analgesic-like psychopharmacological activity. |
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Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide.Síntese e efeito analgésico de (6R, 4S)-p-Mentha-1,8-dien-6-il-metileno-p-toluenossulfonamida.P-ToluenesulfonamideCarvoneMonoterpeneAnalgesic activityAtividade analgésicaAntinoceptive activityAtividade antinoceptivaP-toluenosulfonamidaCarvonamonoterpenoActividade analgésicaAtividade AntinoceptivaAtividades antinoceptivasFarmácia.Química.The synthesis of a monoterpene-based para-toluenesulfonamide is reported starting from naturally occurring (R)- (−)-carvone (1), by 1,2-addition of HCN followed by reduction with lithium aluminum hydride to afford the amino alcohols 3a and 3b. Tosylation of thismixture with p-toluenesulfonyl chloride furnished sulfonamide 4 in 55% overall yield. Compound 4 was evaluated in behavior animal models to investigate its effects on the central nervous system. It showed low toxicity and sedative action in mice, indicating it to be psychoactive. It also caused a decrease in the spontaneous motor activity of mice. This depressant effect was confirmed in the acetic acid-induced writhing test, which demonstrated a significant antinociceptive response more potent than 1. The present results provide evidence that sulfonamide 4 has analgesic-like psychopharmacological activity.Universidade Federal de Campina GrandeBrasilUFCG20092024-08-12T18:18:27Z2024-08-122024-08-12T18:18:27Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260SOUSA, Damião Pergentino de; NÓBREGA, Franklin Ferreira de Farias; ALMEIDA, Reinaldo Nóbrega de; BROCKSOM, Timothy John. Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. Zeitschrift für Naturforschung. B, A journal of Chemical Sciences, v. 64, p. 351-355, 2009. Disponível em: http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260engSOUSA, Damião Pergentino de.NÓBREGA, Franklin Ferreira de Farias.ALMEIDA, Reinaldo Nóbrega de.BROCKSOM, Timothy John.info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFCGinstname:Universidade Federal de Campina Grande (UFCG)instacron:UFCG2024-08-12T18:19:17Zoai:localhost:riufcg/37260Biblioteca Digital de Teses e Dissertaçõeshttp://bdtd.ufcg.edu.br/PUBhttp://dspace.sti.ufcg.edu.br:8080/oai/requestbdtd@setor.ufcg.edu.br || bdtd@setor.ufcg.edu.bropendoar:48512024-08-12T18:19:17Biblioteca Digital de Teses e Dissertações da UFCG - Universidade Federal de Campina Grande (UFCG)false |
dc.title.none.fl_str_mv |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. Síntese e efeito analgésico de (6R, 4S)-p-Mentha-1,8-dien-6-il-metileno-p-toluenossulfonamida. |
title |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. |
spellingShingle |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. SOUSA, Damião Pergentino de. P-Toluenesulfonamide Carvone Monoterpene Analgesic activity Atividade analgésica Antinoceptive activity Atividade antinoceptiva P-toluenosulfonamida Carvona monoterpeno Actividade analgésica Atividade Antinoceptiva Atividades antinoceptivas Farmácia. Química. |
title_short |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. |
title_full |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. |
title_fullStr |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. |
title_full_unstemmed |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. |
title_sort |
Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. |
author |
SOUSA, Damião Pergentino de. |
author_facet |
SOUSA, Damião Pergentino de. NÓBREGA, Franklin Ferreira de Farias. ALMEIDA, Reinaldo Nóbrega de. BROCKSOM, Timothy John. |
author_role |
author |
author2 |
NÓBREGA, Franklin Ferreira de Farias. ALMEIDA, Reinaldo Nóbrega de. BROCKSOM, Timothy John. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
SOUSA, Damião Pergentino de. NÓBREGA, Franklin Ferreira de Farias. ALMEIDA, Reinaldo Nóbrega de. BROCKSOM, Timothy John. |
dc.subject.por.fl_str_mv |
P-Toluenesulfonamide Carvone Monoterpene Analgesic activity Atividade analgésica Antinoceptive activity Atividade antinoceptiva P-toluenosulfonamida Carvona monoterpeno Actividade analgésica Atividade Antinoceptiva Atividades antinoceptivas Farmácia. Química. |
topic |
P-Toluenesulfonamide Carvone Monoterpene Analgesic activity Atividade analgésica Antinoceptive activity Atividade antinoceptiva P-toluenosulfonamida Carvona monoterpeno Actividade analgésica Atividade Antinoceptiva Atividades antinoceptivas Farmácia. Química. |
description |
The synthesis of a monoterpene-based para-toluenesulfonamide is reported starting from naturally occurring (R)- (−)-carvone (1), by 1,2-addition of HCN followed by reduction with lithium aluminum hydride to afford the amino alcohols 3a and 3b. Tosylation of thismixture with p-toluenesulfonyl chloride furnished sulfonamide 4 in 55% overall yield. Compound 4 was evaluated in behavior animal models to investigate its effects on the central nervous system. It showed low toxicity and sedative action in mice, indicating it to be psychoactive. It also caused a decrease in the spontaneous motor activity of mice. This depressant effect was confirmed in the acetic acid-induced writhing test, which demonstrated a significant antinociceptive response more potent than 1. The present results provide evidence that sulfonamide 4 has analgesic-like psychopharmacological activity. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009 2024-08-12T18:18:27Z 2024-08-12 2024-08-12T18:18:27Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260 SOUSA, Damião Pergentino de; NÓBREGA, Franklin Ferreira de Farias; ALMEIDA, Reinaldo Nóbrega de; BROCKSOM, Timothy John. Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. Zeitschrift für Naturforschung. B, A journal of Chemical Sciences, v. 64, p. 351-355, 2009. Disponível em: http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260 |
url |
http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260 |
identifier_str_mv |
SOUSA, Damião Pergentino de; NÓBREGA, Franklin Ferreira de Farias; ALMEIDA, Reinaldo Nóbrega de; BROCKSOM, Timothy John. Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide. Zeitschrift für Naturforschung. B, A journal of Chemical Sciences, v. 64, p. 351-355, 2009. Disponível em: http://dspace.sti.ufcg.edu.br:8080/jspui/handle/riufcg/37260 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Campina Grande Brasil UFCG |
publisher.none.fl_str_mv |
Universidade Federal de Campina Grande Brasil UFCG |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFCG instname:Universidade Federal de Campina Grande (UFCG) instacron:UFCG |
instname_str |
Universidade Federal de Campina Grande (UFCG) |
instacron_str |
UFCG |
institution |
UFCG |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFCG |
collection |
Biblioteca Digital de Teses e Dissertações da UFCG |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UFCG - Universidade Federal de Campina Grande (UFCG) |
repository.mail.fl_str_mv |
bdtd@setor.ufcg.edu.br || bdtd@setor.ufcg.edu.br |
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1809744632886591488 |