Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents

Electrophilic fluorine-mediated dearomative spirocyclization has been developed to synthesize a range of fluoro-substituted spiro-isoxazoline ethers and lactones. The in vitro biological assays of synthesized compounds were probed for anti-viral activity against human cytomegalovirus (HCMV) and cyto...

Descripción completa

Detalles Bibliográficos
Autores principales: Das, Prasanta, Boone, Sarah, Mitra, Dipanwita, Turner, Lindsay, Tandon, Ritesh, Raucher, Drazen, Hamme, Ashton T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9056317/
https://www.ncbi.nlm.nih.gov/pubmed/35518245
http://dx.doi.org/10.1039/d0ra06148d
_version_ 1784697610422976512
author Das, Prasanta
Boone, Sarah
Mitra, Dipanwita
Turner, Lindsay
Tandon, Ritesh
Raucher, Drazen
Hamme, Ashton T.
author_facet Das, Prasanta
Boone, Sarah
Mitra, Dipanwita
Turner, Lindsay
Tandon, Ritesh
Raucher, Drazen
Hamme, Ashton T.
author_sort Das, Prasanta
collection PubMed
description Electrophilic fluorine-mediated dearomative spirocyclization has been developed to synthesize a range of fluoro-substituted spiro-isoxazoline ethers and lactones. The in vitro biological assays of synthesized compounds were probed for anti-viral activity against human cytomegalovirus (HCMV) and cytotoxicity against glioblastomas (GBM6) and triple negative breast cancer (MDA MB 231). Interestingly, compounds 4d and 4n showed significant activity against HCMV (IC(50) ∼ 10 μM), while 4l and 5f revealed the highest cytotoxicity with IC(50) = 36 to 80 μM. The synthetic efficacy and biological relevance offer an opportunity to further drug-discovery development of fluoro-spiro-isoxazolines as novel anti-viral and anti-cancer agents.
format Online
Article
Text
id pubmed-9056317
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90563172022-05-04 Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents Das, Prasanta Boone, Sarah Mitra, Dipanwita Turner, Lindsay Tandon, Ritesh Raucher, Drazen Hamme, Ashton T. RSC Adv Chemistry Electrophilic fluorine-mediated dearomative spirocyclization has been developed to synthesize a range of fluoro-substituted spiro-isoxazoline ethers and lactones. The in vitro biological assays of synthesized compounds were probed for anti-viral activity against human cytomegalovirus (HCMV) and cytotoxicity against glioblastomas (GBM6) and triple negative breast cancer (MDA MB 231). Interestingly, compounds 4d and 4n showed significant activity against HCMV (IC(50) ∼ 10 μM), while 4l and 5f revealed the highest cytotoxicity with IC(50) = 36 to 80 μM. The synthetic efficacy and biological relevance offer an opportunity to further drug-discovery development of fluoro-spiro-isoxazolines as novel anti-viral and anti-cancer agents. The Royal Society of Chemistry 2020-08-17 /pmc/articles/PMC9056317/ /pubmed/35518245 http://dx.doi.org/10.1039/d0ra06148d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Das, Prasanta
Boone, Sarah
Mitra, Dipanwita
Turner, Lindsay
Tandon, Ritesh
Raucher, Drazen
Hamme, Ashton T.
Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
title Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
title_full Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
title_fullStr Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
title_full_unstemmed Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
title_short Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
title_sort synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9056317/
https://www.ncbi.nlm.nih.gov/pubmed/35518245
http://dx.doi.org/10.1039/d0ra06148d
work_keys_str_mv AT dasprasanta synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents
AT boonesarah synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents
AT mitradipanwita synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents
AT turnerlindsay synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents
AT tandonritesh synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents
AT raucherdrazen synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents
AT hammeashtont synthesisandbiologicalevaluationoffluorosubstitutedspiroisoxazolinesaspotentialantiviralandanticanceragents

Ejemplares similares