Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6-yl-methylene-p-toluenesulfonamide.

Detalhes bibliográficos
Autor(a) principal: SOUSA, Damião Pergentino de.
Data de Publicação: 2009
Outros Autores: NÓBREGA, Franklin Ferreira de Farias., ALMEIDA, Reinaldo Nóbrega de., BROCKSOM, Timothy John.
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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spelling 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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