Cargando…
Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines
[Image: see text] A Diels–Alder reaction leading to 4-nitrophenylcyclohexanones followed by a newly developed base-mediated reductive cyclization of the resulting ketone tethered to the nitrobenzene moiety gives access to the hexahydro-2,6-methano-1-benzazocine ring system present in several biologi...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680033/ https://www.ncbi.nlm.nih.gov/pubmed/36329560 http://dx.doi.org/10.1021/acs.joc.2c02205 |
_version_ | 1784834321187602432 |
---|---|
author | Rodríguez, Laura G. Delgado, Ana Ciudad, Carlos J. Noé, Véronique Bonjoch, Josep Bradshaw, Ben |
author_facet | Rodríguez, Laura G. Delgado, Ana Ciudad, Carlos J. Noé, Véronique Bonjoch, Josep Bradshaw, Ben |
author_sort | Rodríguez, Laura G. |
collection | PubMed |
description | [Image: see text] A Diels–Alder reaction leading to 4-nitrophenylcyclohexanones followed by a newly developed base-mediated reductive cyclization of the resulting ketone tethered to the nitrobenzene moiety gives access to the hexahydro-2,6-methano-1-benzazocine ring system present in several biologically interesting natural products such as aspernomine. The scope of the reaction was explored with eight substituted nitrobenzenes, obtaining yields of up to 87%. The highest cytotoxicity was observed in benzazocine 4h, bearing an enone moiety, which was active against eight cancer cell lines. |
format | Online Article Text |
id | pubmed-9680033 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-96800332022-11-23 Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines Rodríguez, Laura G. Delgado, Ana Ciudad, Carlos J. Noé, Véronique Bonjoch, Josep Bradshaw, Ben J Org Chem [Image: see text] A Diels–Alder reaction leading to 4-nitrophenylcyclohexanones followed by a newly developed base-mediated reductive cyclization of the resulting ketone tethered to the nitrobenzene moiety gives access to the hexahydro-2,6-methano-1-benzazocine ring system present in several biologically interesting natural products such as aspernomine. The scope of the reaction was explored with eight substituted nitrobenzenes, obtaining yields of up to 87%. The highest cytotoxicity was observed in benzazocine 4h, bearing an enone moiety, which was active against eight cancer cell lines. American Chemical Society 2022-11-04 2022-11-18 /pmc/articles/PMC9680033/ /pubmed/36329560 http://dx.doi.org/10.1021/acs.joc.2c02205 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Rodríguez, Laura G. Delgado, Ana Ciudad, Carlos J. Noé, Véronique Bonjoch, Josep Bradshaw, Ben Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
title | Base-Mediated Nitrophenyl
Reductive Cyclization for
the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
title_full | Base-Mediated Nitrophenyl
Reductive Cyclization for
the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
title_fullStr | Base-Mediated Nitrophenyl
Reductive Cyclization for
the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
title_full_unstemmed | Base-Mediated Nitrophenyl
Reductive Cyclization for
the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
title_short | Base-Mediated Nitrophenyl
Reductive Cyclization for
the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
title_sort | base-mediated nitrophenyl
reductive cyclization for
the synthesis of hexahydro-2,6-methano-1-benzazocines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680033/ https://www.ncbi.nlm.nih.gov/pubmed/36329560 http://dx.doi.org/10.1021/acs.joc.2c02205 |
work_keys_str_mv | AT rodriguezlaurag basemediatednitrophenylreductivecyclizationforthesynthesisofhexahydro26methano1benzazocines AT delgadoana basemediatednitrophenylreductivecyclizationforthesynthesisofhexahydro26methano1benzazocines AT ciudadcarlosj basemediatednitrophenylreductivecyclizationforthesynthesisofhexahydro26methano1benzazocines AT noeveronique basemediatednitrophenylreductivecyclizationforthesynthesisofhexahydro26methano1benzazocines AT bonjochjosep basemediatednitrophenylreductivecyclizationforthesynthesisofhexahydro26methano1benzazocines AT bradshawben basemediatednitrophenylreductivecyclizationforthesynthesisofhexahydro26methano1benzazocines |