Cargando…

Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells

A novel formal (4 + 1) annulation between N-(o-chloromethyl)aryl amides and 3-chlorooxindoles through in situ generated aza-ortho-QMs with 3-chlorooxindoles is reported for the synthesis of a series of 2,3′-spirobi (indolin)-2′-ones in high yields. Under structured illumination microscopy, compound...

Descripción completa

Detalles Bibliográficos
Autores principales: Li, Huajie, Yu, Zhenjie, Sun, Haoyi, Liu, Bo, Wang, Xin, Shao, Zhe, Wang, Meiling, Xie, Weilin, Yao, Xingang, Yao, Qingqiang, Zhi, Ying
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8904893/
https://www.ncbi.nlm.nih.gov/pubmed/35280257
http://dx.doi.org/10.3389/fphar.2021.821518
_version_ 1784665047760371712
author Li, Huajie
Yu, Zhenjie
Sun, Haoyi
Liu, Bo
Wang, Xin
Shao, Zhe
Wang, Meiling
Xie, Weilin
Yao, Xingang
Yao, Qingqiang
Zhi, Ying
author_facet Li, Huajie
Yu, Zhenjie
Sun, Haoyi
Liu, Bo
Wang, Xin
Shao, Zhe
Wang, Meiling
Xie, Weilin
Yao, Xingang
Yao, Qingqiang
Zhi, Ying
author_sort Li, Huajie
collection PubMed
description A novel formal (4 + 1) annulation between N-(o-chloromethyl)aryl amides and 3-chlorooxindoles through in situ generated aza-ortho-QMs with 3-chlorooxindoles is reported for the synthesis of a series of 2,3′-spirobi (indolin)-2′-ones in high yields. Under structured illumination microscopy, compound 3a is found to change the mitochondrial morphology and induce mitophagy pathway, which might then trigger mitophagy in cancer cells.
format Online
Article
Text
id pubmed-8904893
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Frontiers Media S.A.
record_format MEDLINE/PubMed
spelling pubmed-89048932022-03-10 Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells Li, Huajie Yu, Zhenjie Sun, Haoyi Liu, Bo Wang, Xin Shao, Zhe Wang, Meiling Xie, Weilin Yao, Xingang Yao, Qingqiang Zhi, Ying Front Pharmacol Pharmacology A novel formal (4 + 1) annulation between N-(o-chloromethyl)aryl amides and 3-chlorooxindoles through in situ generated aza-ortho-QMs with 3-chlorooxindoles is reported for the synthesis of a series of 2,3′-spirobi (indolin)-2′-ones in high yields. Under structured illumination microscopy, compound 3a is found to change the mitochondrial morphology and induce mitophagy pathway, which might then trigger mitophagy in cancer cells. Frontiers Media S.A. 2022-02-23 /pmc/articles/PMC8904893/ /pubmed/35280257 http://dx.doi.org/10.3389/fphar.2021.821518 Text en Copyright © 2022 Li, Yu, Sun, Liu, Wang, Shao, Wang, Xie, Yao, Yao and Zhi. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Pharmacology
Li, Huajie
Yu, Zhenjie
Sun, Haoyi
Liu, Bo
Wang, Xin
Shao, Zhe
Wang, Meiling
Xie, Weilin
Yao, Xingang
Yao, Qingqiang
Zhi, Ying
Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells
title Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells
title_full Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells
title_fullStr Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells
title_full_unstemmed Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells
title_short Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells
title_sort efficient synthesis of 2,3′-spirobi (indolin)-2′-ones and preliminary evaluation of their damage to mitochondria in hela cells
topic Pharmacology
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8904893/
https://www.ncbi.nlm.nih.gov/pubmed/35280257
http://dx.doi.org/10.3389/fphar.2021.821518
work_keys_str_mv AT lihuajie efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT yuzhenjie efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT sunhaoyi efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT liubo efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT wangxin efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT shaozhe efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT wangmeiling efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT xieweilin efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT yaoxingang efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT yaoqingqiang efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells
AT zhiying efficientsynthesisof23spirobiindolin2onesandpreliminaryevaluationoftheirdamagetomitochondriainhelacells