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, Zhang; Wang, Meiling; Xie, Weilin; Yao, Xingang; Yao, Qingqiang; Zhi, Yuee

doi:10.3389/fphar.2021.821518

Front. Pharmacol.

2022

DOI: 10.3389/fphar.2021.821518

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

Huajie Li

Zhenjie Yu

Haoyi Sun

et al.

Abstract: 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.

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Cited by 4 publications

References 45 publications

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The effects of sodium–glucose cotransporter 2 inhibitors on the ‘forgotten’ right ventricle

Qu,

Duan,

Chen

2024

ESC Heart Failure

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With the progress in diagnosis, treatment and imaging techniques, there is a growing recognition that impaired right ventricular (RV) function profoundly affects the prognosis of patients with heart failure (HF), irrespective of their left ventricular ejection fraction (LVEF). In addition, right HF (RHF) is a common complication associated with various diseases, including congenital heart disease, myocardial infarction (MI), pulmonary arterial hypertension (PAH) and dilated cardiomyopathy (DCM), and it can manifest at any time after left ventricular assist devices (LVADs). The sodium–glucose cotransporter 2 (SGLT2) inhibition by gliflozins has emerged as a cornerstone medicine for managing type 2 diabetes mellitus (T2DM) and HF, with an increasing focus on its potential to enhance RV function. In this review, we aim to present an updated perspective on the pleiotropic effects of gliflozins on the right ventricle and offer insights into the underlying mechanisms. We can ascertain their advantageous impact on the right ventricle by discussing the evidence obtained in animal models and monumental clinical trials. In light of the pathophysiological changes in RHF, we attempt to elucidate crucial mechanisms regarding their beneficial effects, including alleviation of RV overload, reduction of hyperinsulinaemia and inflammatory responses, regulation of nutrient signalling pathways and cellular energy metabolism, inhibition of oxidative stress and myocardial fibrosis, and maintenance of ion balance. Finally, this drug class's potential application and benefits in various clinical settings are described, along with a prospective outlook on future clinical practice and research directions.

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The effects of sodium–glucose cotransporter 2 inhibitors on the ‘forgotten’ right ventricle

Qu,

Duan,

Chen

2024

ESC Heart Failure

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Probing the dynamic crosstalk of lysosomes and mitochondria with structured illumination microscopy

Xu,

Qiu,

Tian

et al. 2023

TrAC Trends in Analytical Chemistry

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Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-ortho-quinone Methide Precursor

et al. 2023

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The chemoselective annulation of aza-ortho-quinone methide generated by in situ o-chloromethyl sulfonamide has been achieved with bifunctional acyclic olefin. This efficient approach provides access to the diastereoselective synthesis of functionalized tetrahydroquinoline derivatives containing indole scaffolds through the inverse-electron-demand aza-Diels–Alder reaction under mild reaction conditions with excellent results (up to 93% yield, > 20:1 dr). Moreover, this article realized the cyclization of α-halogeno hydrazone with electron-deficient alkene affording the tetrahydropyridazine derivatives, which had never been reported.

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

Cited by 4 publications

References 45 publications

The effects of sodium–glucose cotransporter 2 inhibitors on the ‘forgotten’ right ventricle

The effects of sodium–glucose cotransporter 2 inhibitors on the ‘forgotten’ right ventricle

Probing the dynamic crosstalk of lysosomes and mitochondria with structured illumination microscopy

Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-ortho-quinone Methide Precursor

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