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Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()

A reaction of 2-acetyl-3-acylaminobenzo[b]furans (9d–o) with Vilsmeier (VM) reagent afforded a mixture of (E)- and (Z)-{(E)-2-aralkenylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylidene}acetaldehydes (5) with a characteristic exo-formylmethylene group on the oxazine ring. The Z-isomer was more stable than the...

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Autores principales: Tabuchi, Yukako, Ando, Yuko, Kanemura, Hidemi, Kawasaki, Ikuo, Ohishi, Takahiro, Koida, Masao, Fukuyama, Ryo, Nakamuta, Hiromichi, Ohta, Shunsaku, Nishide, Kiyoharu, Ohishi, Yoshitaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127799/
https://www.ncbi.nlm.nih.gov/pubmed/19406645
http://dx.doi.org/10.1016/j.bmc.2009.04.017
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author Tabuchi, Yukako
Ando, Yuko
Kanemura, Hidemi
Kawasaki, Ikuo
Ohishi, Takahiro
Koida, Masao
Fukuyama, Ryo
Nakamuta, Hiromichi
Ohta, Shunsaku
Nishide, Kiyoharu
Ohishi, Yoshitaka
author_facet Tabuchi, Yukako
Ando, Yuko
Kanemura, Hidemi
Kawasaki, Ikuo
Ohishi, Takahiro
Koida, Masao
Fukuyama, Ryo
Nakamuta, Hiromichi
Ohta, Shunsaku
Nishide, Kiyoharu
Ohishi, Yoshitaka
author_sort Tabuchi, Yukako
collection PubMed
description A reaction of 2-acetyl-3-acylaminobenzo[b]furans (9d–o) with Vilsmeier (VM) reagent afforded a mixture of (E)- and (Z)-{(E)-2-aralkenylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylidene}acetaldehydes (5) with a characteristic exo-formylmethylene group on the oxazine ring. The Z-isomer was more stable than the E-isomer. The Z-isomers ((Z)-5) were reacted with phosphonate reagents under two different conditions to obtain various butadiene derivatives (12) containing benzo[b]furo[3,2-d][1,3]oxazine skeleton. Typical compounds (5 and 12) were evaluated for their anti-osteoclastic bone resorption activity, antagonistic activity for the cysLT1 receptor and growth inhibitory activity for MIA PaCa-2 and MCF-7. Compounds 12f and 12j showed potent anti-osteoclastic bone resorption activity comparable to E(2) (17β-estradiol).
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spelling pubmed-71277992020-04-08 Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity() Tabuchi, Yukako Ando, Yuko Kanemura, Hidemi Kawasaki, Ikuo Ohishi, Takahiro Koida, Masao Fukuyama, Ryo Nakamuta, Hiromichi Ohta, Shunsaku Nishide, Kiyoharu Ohishi, Yoshitaka Bioorg Med Chem Article A reaction of 2-acetyl-3-acylaminobenzo[b]furans (9d–o) with Vilsmeier (VM) reagent afforded a mixture of (E)- and (Z)-{(E)-2-aralkenylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylidene}acetaldehydes (5) with a characteristic exo-formylmethylene group on the oxazine ring. The Z-isomer was more stable than the E-isomer. The Z-isomers ((Z)-5) were reacted with phosphonate reagents under two different conditions to obtain various butadiene derivatives (12) containing benzo[b]furo[3,2-d][1,3]oxazine skeleton. Typical compounds (5 and 12) were evaluated for their anti-osteoclastic bone resorption activity, antagonistic activity for the cysLT1 receptor and growth inhibitory activity for MIA PaCa-2 and MCF-7. Compounds 12f and 12j showed potent anti-osteoclastic bone resorption activity comparable to E(2) (17β-estradiol). Elsevier Ltd. 2009-06-01 2009-04-12 /pmc/articles/PMC7127799/ /pubmed/19406645 http://dx.doi.org/10.1016/j.bmc.2009.04.017 Text en Copyright © 2009 Elsevier Ltd. All rights reserved. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Tabuchi, Yukako
Ando, Yuko
Kanemura, Hidemi
Kawasaki, Ikuo
Ohishi, Takahiro
Koida, Masao
Fukuyama, Ryo
Nakamuta, Hiromichi
Ohta, Shunsaku
Nishide, Kiyoharu
Ohishi, Yoshitaka
Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
title Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
title_full Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
title_fullStr Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
title_full_unstemmed Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
title_short Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
title_sort preparation of novel (z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity()
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127799/
https://www.ncbi.nlm.nih.gov/pubmed/19406645
http://dx.doi.org/10.1016/j.bmc.2009.04.017
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