Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry

Autores
GURGONE, LUCIA; la Venia, Agustina; Caprioglio, Diego; Riveira, Martín Jorge
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The chemistry of phytocannabinoids has witnessed renewed interest these last decades as a consequence of reduced restrictions, research on the endocannabinoid system and the development of approved therapeutic treatments based on cannabinoids. The medicinal cannabinoid market constitutes a prolific scenario in current medicine. Most studies, however, have focused on only two major components of Cannabis sativa L., namely, cannabidiol (CBD, 2) and (−)-Δ9-trans-tetrahydrocannabinol (Δ9-trans-THC, 6a), the latter being the main psychoactive compound of this plant. The cis-diastereoisomer of Δ9-trans-THC, Δ9-cis-THC, although also present in the same plant, has been less investigated in terms of biological, medicinal and synthetic perspectives. Interestingly, the cis-fused tetrahydrobenzo [c]chromene motif present in Δ9-cis-THC is embedded in many other natural products which also exhibit interesting biological activities such as anticancer, antifungal, and antiparasitic. This review discloses synthetic approaches that have been established towards the cis-fused tetrahydroisochromene system of Δ9-cis-THC.
Fil: GURGONE, LUCIA. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Caprioglio, Diego. Universita  del Piemonte Orientale; Italia
Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
STEREOSELECTIVE SYNTHESIS
CANNABINOIDS
THC
ISOCHROMENES
HETERO-DIELS-ALDER
BIOACTIVE NATURAL PRODUCTS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/254842
Acceder
id CONICETDig_ff9fc74eec400db2bbad4e0642698d02
oai_identifier_str oai:ri.conicet.gov.ar:11336/254842
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistryGURGONE, LUCIAla Venia, AgustinaCaprioglio, DiegoRiveira, Martín JorgeSTEREOSELECTIVE SYNTHESISCANNABINOIDSTHCISOCHROMENESHETERO-DIELS-ALDERBIOACTIVE NATURAL PRODUCTShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The chemistry of phytocannabinoids has witnessed renewed interest these last decades as a consequence of reduced restrictions, research on the endocannabinoid system and the development of approved therapeutic treatments based on cannabinoids. The medicinal cannabinoid market constitutes a prolific scenario in current medicine. Most studies, however, have focused on only two major components of Cannabis sativa L., namely, cannabidiol (CBD, 2) and (−)-Δ9-trans-tetrahydrocannabinol (Δ9-trans-THC, 6a), the latter being the main psychoactive compound of this plant. The cis-diastereoisomer of Δ9-trans-THC, Δ9-cis-THC, although also present in the same plant, has been less investigated in terms of biological, medicinal and synthetic perspectives. Interestingly, the cis-fused tetrahydrobenzo [c]chromene motif present in Δ9-cis-THC is embedded in many other natural products which also exhibit interesting biological activities such as anticancer, antifungal, and antiparasitic. This review discloses synthetic approaches that have been established towards the cis-fused tetrahydroisochromene system of Δ9-cis-THC.Fil: GURGONE, LUCIA. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Caprioglio, Diego. Universita  del Piemonte Orientale; ItaliaFil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFrontiers Media2023-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/254842GURGONE, LUCIA; la Venia, Agustina; Caprioglio, Diego; Riveira, Martín Jorge; Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry; Frontiers Media; Frontiers in Natural Products; 2; 8-2023; 1-112813-2602CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.frontiersin.org/articles/10.3389/fntpr.2023.1225627/fullinfo:eu-repo/semantics/altIdentifier/doi/10.3389/fntpr.2023.1225627info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:47:18Zoai:ri.conicet.gov.ar:11336/254842instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:47:18.745CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
title Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
spellingShingle Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
GURGONE, LUCIA
STEREOSELECTIVE SYNTHESIS
CANNABINOIDS
THC
ISOCHROMENES
HETERO-DIELS-ALDER
BIOACTIVE NATURAL PRODUCTS
title_short Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
title_full Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
title_fullStr Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
title_full_unstemmed Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
title_sort Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry
dc.creator.none.fl_str_mv GURGONE, LUCIA
la Venia, Agustina
Caprioglio, Diego
Riveira, Martín Jorge
author GURGONE, LUCIA
author_facet GURGONE, LUCIA
la Venia, Agustina
Caprioglio, Diego
Riveira, Martín Jorge
author_role author
author2 la Venia, Agustina
Caprioglio, Diego
Riveira, Martín Jorge
author2_role author
author
author
dc.subject.none.fl_str_mv STEREOSELECTIVE SYNTHESIS
CANNABINOIDS
THC
ISOCHROMENES
HETERO-DIELS-ALDER
BIOACTIVE NATURAL PRODUCTS
topic STEREOSELECTIVE SYNTHESIS
CANNABINOIDS
THC
ISOCHROMENES
HETERO-DIELS-ALDER
BIOACTIVE NATURAL PRODUCTS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The chemistry of phytocannabinoids has witnessed renewed interest these last decades as a consequence of reduced restrictions, research on the endocannabinoid system and the development of approved therapeutic treatments based on cannabinoids. The medicinal cannabinoid market constitutes a prolific scenario in current medicine. Most studies, however, have focused on only two major components of Cannabis sativa L., namely, cannabidiol (CBD, 2) and (−)-Δ9-trans-tetrahydrocannabinol (Δ9-trans-THC, 6a), the latter being the main psychoactive compound of this plant. The cis-diastereoisomer of Δ9-trans-THC, Δ9-cis-THC, although also present in the same plant, has been less investigated in terms of biological, medicinal and synthetic perspectives. Interestingly, the cis-fused tetrahydrobenzo [c]chromene motif present in Δ9-cis-THC is embedded in many other natural products which also exhibit interesting biological activities such as anticancer, antifungal, and antiparasitic. This review discloses synthetic approaches that have been established towards the cis-fused tetrahydroisochromene system of Δ9-cis-THC.
Fil: GURGONE, LUCIA. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Caprioglio, Diego. Universita  del Piemonte Orientale; Italia
Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description The chemistry of phytocannabinoids has witnessed renewed interest these last decades as a consequence of reduced restrictions, research on the endocannabinoid system and the development of approved therapeutic treatments based on cannabinoids. The medicinal cannabinoid market constitutes a prolific scenario in current medicine. Most studies, however, have focused on only two major components of Cannabis sativa L., namely, cannabidiol (CBD, 2) and (−)-Δ9-trans-tetrahydrocannabinol (Δ9-trans-THC, 6a), the latter being the main psychoactive compound of this plant. The cis-diastereoisomer of Δ9-trans-THC, Δ9-cis-THC, although also present in the same plant, has been less investigated in terms of biological, medicinal and synthetic perspectives. Interestingly, the cis-fused tetrahydrobenzo [c]chromene motif present in Δ9-cis-THC is embedded in many other natural products which also exhibit interesting biological activities such as anticancer, antifungal, and antiparasitic. This review discloses synthetic approaches that have been established towards the cis-fused tetrahydroisochromene system of Δ9-cis-THC.
publishDate 2023
dc.date.none.fl_str_mv 2023-08
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/254842
GURGONE, LUCIA; la Venia, Agustina; Caprioglio, Diego; Riveira, Martín Jorge; Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry; Frontiers Media; Frontiers in Natural Products; 2; 8-2023; 1-11
2813-2602
CONICET Digital
CONICET
url http://hdl.handle.net/11336/254842
identifier_str_mv GURGONE, LUCIA; la Venia, Agustina; Caprioglio, Diego; Riveira, Martín Jorge; Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry; Frontiers Media; Frontiers in Natural Products; 2; 8-2023; 1-11
2813-2602
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.frontiersin.org/articles/10.3389/fntpr.2023.1225627/full
info:eu-repo/semantics/altIdentifier/doi/10.3389/fntpr.2023.1225627
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Frontiers Media
publisher.none.fl_str_mv Frontiers Media
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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