Sn(OTf)2-Catalyzed (3 + 2) Cycloaddition/Sulfur Rearrangement Reaction of Donor-Acceptor Cyclopropanes with Indoline-2-thiones.

The (3 + 2) cycloaddition/sulfur rearrangement reaction of donor-acceptor cyclopropanes bearing a single keto acceptor with indoline-2-thiones has been realized. Under the catalysis of Sn(OTf)2, a series of functionalized 3-indolyl-4,5-dihydrothiophenes were synthesized with moderate to excellent yields.

Yb(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor-Acceptor Cyclopropanes.

A Yb(OTf)3-catalyzed formal (4 + 3) cycloaddition reaction of donor-acceptor cyclopropanes with 3-benzylideneindoline-2-thiones as sulfur-containing 4π components has been successfully achieved. A series of functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. The reaction described herein represented the inaugural (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.

AlCl3-mediated ring-opening reactions of indoline-2-thiones with acyl cyclopropanes, bi-cyclopropanes and spirocyclic cyclopropanes.

AlCl3-mediated nucleophilic ring-opening reactions of indoline-2-thiones with various acyl cyclopropanes, bi-cyclopropanes and spirocyclic cyclopropanes were investigated. A series of ketones functionalized with indolylthio groups were synthesized in yields ranging from moderate to good. Moreover, chemical transformations of 4-indolylthio butan-1-ones to dihydro-2H-thiepino[2,3-b]indoles and sulfone were carried out to further expand both synthetic utility and structural complexity.

MgI2-Catalyzed Nucleophilic Ring-Opening Reactions of Donor-Acceptor Cyclopropanes with Indoline-2-thiones.

MgI2-catalyzed nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with indoline-2-thiones as easy-to-handle sulfur nucleophiles were investigated. A series of functionalized γ-indolylthio butyric acid derivatives were synthesized in good to excellent yields under mild reaction conditions. Furthermore, the thioether functionalized ring-opening products could be transformed to sulfone and methionine analogues.

Synthesis of acyloxy-2H-azirine and sulfonyloxy-2H-azirine derivatives via a one-pot reaction of ß-enamino esters, PIDA and carboxylic acid or sulfonic acid.

PIDA mediated oxidative acyloxylation/azirination and sulfonyloxylation/azirination of ß-enamino esters were investigated. A series of functionalized acyloxy-2H-azirine and sulfonyloxy-2H-azirine derivatives was synthesized in moderate to good yields. This represents the first oxidative sulfonyloxylation/azirination of ß-enamino esters with PIDA and sulfonic acid for access to sulfonyloxy-2H-azirine. Hypervalent iodine reagents enable cascade C-O/C-N bond formation. Furthermore, a possible reaction pathway was proposed based on the experimental results.

Bu-Yin-Qian-Zheng Formula Ameliorates MPP+-Induced Mitochondrial Dysfunction in Parkinson's Disease via Parkin.

As a typical traditional Chinese medicine, Bu-Yin-Qian-Zheng Formula (BYQZF) has been shown to have neuroprotective effects in patients with Parkinson's disease (PD), particularly by ameliorating mitochondrial dysfunction and regulating expression of the parkin protein. However, the underlying mechanisms by which BYQZF affects mitochondrial function through parkin are unclear. Accordingly, in this study, we evaluated the mechanisms by which BYQZF ameliorates mitochondrial dysfunction through parkin in PD. We constructed a parkin-knockdown cell model and performed fluorescence microscopy to observe transfected SH-SY5Y cells. Quantitative real-time reverse transcription polymerase chain reaction and western blotting were conducted to detect the mRNA and protein expression levels of parkin. Additionally, we evaluated the cell survival rates, ATP levels, mitochondrial membrane potential (ΔΨm), mitochondrial morphology, parkin protein expression, PINK1 protein expression, and mitochondrial fusion and fission protein expression after treatment with MPP+ and BYQZF. Our results showed that cell survival rates, ATP levels, ΔΨm, mitochondrial morphology, parkin protein levels, PINK1 protein levels, and mitochondrial fusion protein levels were reduced after MPP+ treatment. In contrast, mitochondrial fission protein levels were increased after MPP+ treatment. Moreover, after transient transfection with a negative control plasmid, the above indices were significantly increased by BYQZF. However, there were no obvious differences in these indices after transient transfection with a parkin-knockdown plasmid. Our findings suggest that BYQZF has protective effects on mitochondrial function in MPP+-induced SH-SY5Y cells via parkin-dependent regulation of mitochondrial dynamics.

Da-Bu-Yin-Wan and Qian-Zheng-San Ameliorate Mitochondrial Dynamics in the Parkinson's Disease Cell Model Induced by MPP.

To investigate the effect of Da-Bu-Yin-Wan and Qian-Zheng-San (DBYW and QZS) on mitochondrial mass in Parkinson's disease (PD) cell model induced by 1-Methyl-4-phenylpyridinium Ion (MPP+). The SH-SY5Y cell was selected and treated with MPP+. The PD model was intervened with DBYW and QZS. CCK-8 method was used to detect the survival rate of cells in each group. Mitochondria was labeled by mitoTracker®Red CMXRos probe and observed by laser scanning confocal microscope, and ImageJ software was used to process images and measure mitochondrial form factors; Tetramethylrhodamine methyl ester was used to detect mitochondrial membrane potential (ΔΨm); Luciferase method was used to detect cellular ATP levels; Western-Blot technique was applied to detect the expression levels of Parkin protein, and the expression levels of Mfn1, Mfn2, OPA1, Drp1, and Fis1. We found that DBYW and QZS treatment significantly increased the cell survival rate, form factor (F-factor), mitochondrial activity and ΔΨm after MPP+ treatment, while the increase of ATP levels was not significant. In addition, the results of western blot analysis showed that the MPP+ induced increase in the expression of Drp1 and Fis1, as well as decrease in Parkin, Mfn1, Mfn2, and OPA1 were all partially revised by DBYW and QZS. In summary, our data strongly suggested that DBYW and QZS treatment can exert protective effects against PD related neuronal injury through regulation the homeostasis between mitochondrial fission and fusion.

Ruthenium-catalyzed synthesis of indole derivatives from N-aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides.

Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.