DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

Gao, Bao; Liu, Xiaojun; Zhang, Xiuli; Yan, Qian; Yang, Ruiting; Jiang, Tao

doi:10.1055/s-0041-1737341

Cited by 4 publications

(2 citation statements)

References 56 publications

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“…We cannot also overlook in our discussion a potential biological action of the solvent/vehicle used in our experiments, 2.5% DMSO diluted in PBS and given in a dose of 0.125 µl of DMSO per gram of body weight. We chose DMSO as a vehicle for SAL based on a large amount of previous data in the literature [ 42 , 43 , 70 ]. DMSO is routinely used in biological research as a solvent and a cryopreservative in bone marrow and organ transplants.…”

Section: Discussionmentioning

confidence: 99%

Modulation of the endoplasmic reticulum stress and unfolded protein response mitigates the behavioral effects of early-life stress

et al. 2023

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Background Early-life stress (ELS) affects brain development and increases the risk of mental disorders associated with the dysfunction of the medial prefrontal cortex (mPFC). The mechanisms of ELS action are not well understood. Endoplasmic reticulum (ER) stress and the unfolded protein response (UPR) are cellular processes involved in brain maturation through the regulation of pro-survival or proapoptotic processes. We hypothesized that ER stress and the UPR in the mPFC are involved in the neurobiology of ELS. Methods We performed a maternal separation (MS) procedure from postnatal days 1 to 14 in rats. Before each MS, pups were injected with an inhibitor of ER stress, salubrinal or a vehicle. The mRNA and protein expression of UPR and apoptotic markers were evaluated in the mPFC using RT-qPCR and Western blot methods, respectively. We also estimated the numbers of neurons and glial cells using stereological methods. Additionally, we assessed behavioral phenotypes related to fear, anhedonia and response to psychostimulants. Results MS slightly enhanced the activation of the UPR in juveniles and modulated the expression of apoptotic markers in juveniles and preadolescents but not in adults. Additionally, MS did not affect the numbers of neurons and glial cells at any age. Both salubrinal and vehicle blunted the expression of UPR markers in juvenile and preadolescent MS rats, often in a treatment-specific manner. Moreover, salubrinal and vehicle generally alleviated the behavioral effects of MS in preadolescent and adult rats. Conclusions Modulation of ER stress and UPR processes may potentially underlie susceptibility or resilience to ELS.

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Section: Discussionmentioning

confidence: 99%

Modulation of the endoplasmic reticulum stress and unfolded protein response mitigates the behavioral effects of early-life stress

et al. 2023

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“…To the best of our knowledge, a straightforward addition reaction of C–S bonds to alkynes to realize stereoselective bisthiolation of terminal alkynes has not been documented. In connection with our interests in the synthesis of sulfur-containing organic compounds, herein, we report a novel method for the bisthiolation of terminal alkynes with allyl phenyl sulfides as the sulfur source, in which the sulfur-containing moiety was incorporated into the desired ( Z )-1,2-diarylthio-1-akenes via two sequential C–S bond cleavage. Compared with the method reported by Sonoda, our method shows high functional group tolerance and exhibits high reactivity for various substituted alkynes and allyl phenyl sulfides.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Highly Chemo- and Stereoselective Bisthiolation of Terminal Alkynes with Allyl Phenyl Sulfides via C–S Bond Cleavage

et al. 2022

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A facile and general method for palladium-catalyzed stereoselective bisthiolation of terminal alkynes with allyl phenyl sulfides has been developed. The scope and versatility of the reaction have been demonstrated, and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction, providing the desired (Z)-1,2-dithio-1-alkenes in moderate to good yields. Preliminary mechanistic studies demonstrated that the sulfur source of the desired products may be successively incorporated into alkynes via C−S bond cleavage of two molecules of allyl phenyl sulfides and ruled out the possibility of vinyl sulfides, alkynyl sulfides, and disulfide intermediates being involved in this reaction.

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Palladium-Catalyzed Thiocarbonylation of Aryl Iodides with S-Aryl Thioformates via Thioester Transfer

et al. 2022

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Herein we reported a novel approach to synthesize thioesters with S-aryl thioformates as thioester sources. The reaction proceeded at ambient temperature using widely available starting ingredients, wherein the thioester moiety was smoothly transferred to aryl iodides from S-aryl thioformates. A variety of substrates with various electronic natures were all tolerated under the reaction conditions to furnish desirable thioesters in ranges from moderate to excellent yields. The gram-scale reaction was also conducted, and there was virtually little change in chemical yield, indicating that large-scale synthesis of thioesters may be viable using this method.

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DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

Cited by 4 publications

References 56 publications

Modulation of the endoplasmic reticulum stress and unfolded protein response mitigates the behavioral effects of early-life stress

Modulation of the endoplasmic reticulum stress and unfolded protein response mitigates the behavioral effects of early-life stress

Palladium-Catalyzed Highly Chemo- and Stereoselective Bisthiolation of Terminal Alkynes with Allyl Phenyl Sulfides via C–S Bond Cleavage

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides with S-Aryl Thioformates via Thioester Transfer

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