21713-53-1Relevant academic research and scientific papers
Alleviating Cellular Oxidative Stress through Treatment with Superoxide-Triggered Persulfide Prodrugs
Dillon, Kearsley M.,Li, Zhao,Matson, John B.,Wang, Yin,Winckler, Ethan W.
, p. 16698 - 16704 (2020)
Overproduction of superoxide anion (O2.?), the primary cellular reactive oxygen species (ROS), is implicated in various human diseases. To reduce cellular oxidative stress caused by overproduction of superoxide, we developed a compound that reacts with O2.? to release a persulfide (RSSH), a type of reactive sulfur species related to the gasotransmitter hydrogen sulfide (H2S). Termed SOPD-NAC, this persulfide donor reacts specifically with O2.?, decomposing to generate N-acetyl cysteine (NAC) persulfide. To enhance persulfide delivery to cells, we conjugated the SOPD motif to a short, self-assembling peptide (Bz-CFFE-NH2) to make a superoxide-responsive, persulfide-donating peptide (SOPD-Pep). Both SOPD-NAC and SOPD-Pep delivered persulfides/H2S to H9C2 cardiomyocytes and lowered ROS levels as confirmed by quantitative in vitro fluorescence imaging studies. Additional in vitro studies on RAW 264.7 macrophages showed that SOPD-Pep mitigated toxicity induced by phorbol 12-myristate 13-acetate (PMA) more effectively than SOPD-NAC and several control compounds, including common H2S donors.
Electrochemical Enabled Cascade Phosphorylation of N?H/O?H/S?H Bonds with P?H Compounds: An Efficient Access to P(O)-X Bonds
Abdukader, Ablimit,Dong, Xiaojuan,Jin, Weiwei,Liu, Chenjiang,Wang, Bin,Wang, Ruige,Xia, Yu,Xue, Fei,Zhang, Yonghong
supporting information, p. 14931 - 14935 (2021/10/06)
An electrochemical three component cascade phosphorylation reaction of various heteroatoms-containing nucleophiles including carbazoles, indoles, phenols, alcohols, and thiols with Ph2PH has been established. Electricity is used as the “traceless” oxidant and water and air are utilized as the “green” oxygen source. All kinds of structurally diverse organophosphorus compounds with P(O)-N/P(O)-O/P(O)-S bonds are assembled in moderate to excellent yields (three categories of phosphorylation products, 50 examples, up to 97 % yield). A tentative free radical course is put forward to rationalize the reaction procedure.
Tf2O/DMSO-Promoted P-O and P-S Bond Formation: A Scalable Synthesis of Multifarious Organophosphinates and Thiophosphates
Shen, Jian,Li, Qi-Wei,Zhang, Xin-Yue,Wang, Xue,Li, Gui-Zhi,Li, Wen-Zuo,Yang, Shang-Dong,Yang, Bin
supporting information, p. 1541 - 1547 (2021/04/05)
A Tf2O/DMSO-based system for the dehydrogenative coupling of a wide range of alcohols, phenols, thiols, and thiophenols with diverse phosphorus reagents has been developed. This metal- and strong-oxidant-free strategy provides a facile approach to a great variety of organophosphinates and thiophosphates. The simple reaction system, good functional-group tolerance, and broad substrate scope enable the application of this method to the modification of natural products and the direct synthesis of bioactive molecules and flame retardants.
Base-promoted selective O-phosphorylation of aryl triflates with P(O)-H compounds
Wang, Mingyue,Yang, Jia,Wang, Shuai,Zhong, Hong
, (2020/05/05)
Compared to previous transition metal-catalyzed C-phosphorylation reactions for constructing C–P bonds, in the absence of transition metal catalysts and ligands, a direct O-phosphorylation of aryl triflates selectively occurred with P(O)-H compounds in the presence of a base via the construction of O–P bonds. This transformation proceeds under simple and mild conditions, and provides a new method for the preparation of valuable organophosphoryl compounds from readily available P(O)-H compounds and triflates.
Highly Efficient and Convenient Access to Phosphinates via CHCl3-Assisted Direct Phosphorylation between R2P(O)H and ROH by Phosphonium Salt Catalysis
Jiang, Zhiyu,Wang, Tianli,Yu, Xiaojun,Zhang, Hong-Su,Zhang, Song
supporting information, (2020/05/25)
A mild, efficient, convenient and scalable method to synthesize phosphinates via direct phosphorylation between R2P(O)H and ROH was developed. All aromatic substrates completed this transformation with excellent yields (up to 98 %), and preliminary mechanistic studies suggest that a carbene-involving process from CHCl3 to CH2Cl2 facilitates the phosphorylation.
Preparation method of compound containing P-O bond or P-S bond
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Paragraph 0292-0296, (2020/09/12)
The invention discloses a preparation method of a compound containing a P-O bond or a P-S bond. The method comprises the following steps: a compound containing hydroxyl or sulfydryl and a phosphorus reagent are taken as initial raw materials; then, the initial raw materials are put into an inert gas atmosphere; and under the action of trifluoromethanesulfonic anhydride (Tf2O) and dimethyl sulfoxide (DMSO), the compound containing hydroxyl or sulfydryl, the phosphorus reagent, the trifluoromethanesulfonic anhydride and the dimethyl sulfoxide in a molar ratio of (1-5): (1-2.5): (2-3): 2 react inan organic solvent at the reaction temperature of 25-100 DEG C for 6-20 hours to obtain the compound with the structural general formula (I). The reagents used in the method are low in toxicity and environmentally friendly, and use of precious metal catalysts high in price and toxicity is avoided. The reagents trifluoromethanesulfonic anhydride (Tf2O) and dimethyl sulfoxide (DMSO) used in the method are low in toxicity and very low in cost, so that the method is green, environment-friendly, high in economy and suitable for large-scale production.
Phosphonate compound, preparation method and application thereof
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Paragraph 0062-0064, (2020/04/02)
The invention provides a phosphonate compound, a preparation method and application thereof. The method includes the steps of: in a nitrogen atmosphere, mixing a P(O)-H compound, an aryl trifluoromethanesulfonate compound, an alkali reagent and an organic solvent, carrying out stirring reaction at 80-130DEG C for 15-24h, and conducting cooling, washing and extraction at the end of reaction to obtain an organic phase; drying and distilling the obtained organic phase to obtain the phosphonate compound; wherein the molar ratio of the P(O)-H compound, the aryl trifluoromethanesulfonate compound and the alkali reagent is 1-3:1:2-3. The method has the advantages of simple and easily available raw materials, simple reaction conditions, wide functional group compatibility, high yield and wide applicability, the structural formula of the obtained phosphonate compound is shown as formula (I) in the specification, and the extraction rate of the phosphonate compound applied to the field of lithiumion extraction is 53% or above.
A mitochondria-targeted nitric oxide donor triggered by superoxide radical to alleviate myocardial ischemia/reperfusion injury
Hou, Jingli,He, Haiyan,Huang, Saipeng,Qian, Meng,Wang, Jie,Tan, Xiaoli,Han, Guifang,Song, Yuguang,Xu, Zhelong,Liu, Yangping
supporting information, p. 1205 - 1208 (2019/02/01)
A novel mitochondria-targeted superoxide-responsive nitric oxide donor was developed by incorporation of diphenylphosphinyl and triphenylphosphonium groups into diazeniumdiolate, enabling remarkable protection against ischemia/reperfusion injury in H9c2 c
A scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with RSH/ROH
Li, Yujun,Yang, Qi,Yang, Liquan,Lei, Ning,Zheng, Ke
supporting information, p. 4981 - 4984 (2019/05/21)
A practical, scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with thiols, phenols and alcohols in both an undivided cell and a continuous-flow setup is disclosed. Its broad substrate scope (>50 examples), good functional-group tolerance and scalability (>10 g) show potential for practical synthesis. A preliminary mechanistic study suggests that the phosphorus radicals are involved in the catalytic cycle.
METAL-FREE DIRECT ARYLATION OF DIALKYL PHOSPHONATES FOR THE SYNTHESIS OF MIXED ALKYL ARYL PHOSPHONATES
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Paragraph 00424; 00444, (2019/02/15)
Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This
