Organic Chemistry Frontiers
·
2015
·Vol. 2
·期 5
·470-475
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IF 0
Jinqiang Kuang,Xinjun Tang,Shengming Ma
Zinc diiodide has been identified as an effective reagent for the efficient synthesis of trisubstituted allenes from propargylic amines. Compared to CdI2 this protocol offers a green approach. Due to the easy preparation of propargylic amines through the method developed by this group, this method provides a two-step synthesis of trisubstituted allenes from 1-alkynes, ketones, and pyrrolidine. Finally, an efficient synthesis of such trisubstituted allenes from 1-alkynes, ketones, and pyrrolidine via simple filtration has been developed. Compared with the CdI2-mediated protocol, the current protocol enjoys a much wider scope for ketones and affords functionalized allenes without further cyclization in some substrates.
研究领域:
有机化学
·
合成化学
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产品关联
DOI
COLLOID AND POLYMER SCIENCE
·
2016
·Vol. 295
·期 2
·307-315
·
IF 1.89
Jong Kwanghyok,Ju Benzhi
Thermo-responsive polymers present great advantages in the targeted delivery and release of drugs. In this study, a novel type of thermo-responsive polymer called 2-hydroxy-3-(2-propynyloxy) propyl hydroxyethyl starch (PyHES) was synthesized via hydrophobic modification of hydroxyl groups in hydroxyethyl starch (HES) with 2- propynylglycidyl ether (PGE). Aqueous PyHES solutions with an appropriate degree of substitution (DS) of hydrophobic propynyl groups exhibited strong thermo-responsive properties as well as a cloud point temperature (Tcp) that could be tuned within a range of 31 to 48 °C by changing the DS or PyHES concentrations. Moreover, the Tcp decreased with increases in the DS or the concentration of PyHES. The Tcp of PyHES had a linear relationship with DS, and DLS characterizations indicated that PyHES can form thermo-responsive micellar nanoparticles in aqueous solutions. In addition, PyHES can be further functionalized via click reaction of the propynyl group.
研究领域:
材料科学
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生物医学工程
·
药物递送系统
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产品关联
DOI
高影响因子
Nature Communications
·
2013
·Vol. 4
·期 1
·1-7
·
IF 10.015
Tang Xinjun,Zhu Can,Cao Tao,Kuang Jingqiang,Lin Weilong,Ni Shengjun,Zhang Jiasheng,Ma Shengming
Allenes are important building blocks in organic synthesis and have attracted much attention from researchers worldwide. So far, mono- and 1,3-disubstituted allenes can be prepared easily by applying the allenylation of terminal alkynes reaction of aldehydes. However, trisubstituted allenes have never been reported using this reaction due to the extremely low reactivity of ketones. Here, we report the one-pot synthesis of trisubstituted allenes from terminal alkynes and ketones utilizing cadmium iodide as the mediator. With this protocol, a series of different allenes, including 1,5-bisallenes and optically active allenols, which are especially important in synthetic chemistry, have been successfully prepared.
研究领域:
有机化学
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合成化学
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产品关联
DOI
PubMed
高影响因子
Frontiers in Plant Science
·
2022
·
IF 6.627
Lei Wenli,Song Yuyang,Long Ai,Que Yanyan,He Shuzhong,Zhong Hang,Chen Yang
The medicinal plants were wildly library of natural products in drug discovery. The most active molecules with seven-membered rings skeleton represent a challenge for construction. A stereoselectivity (4 + 3) cycloadditions between allenyl ethers and substituted furans induced by chiral auxiliaries has been investigated. And the results showed significant stereoselectivities and regioselectivities. The optical cycloadducts with an oxygen-substituted seven-membered ring framework were generated by removing chiral auxiliaries under acidic conditions. The antiproliferative activity of the novel compounds displayed moderate antiproliferative effects toward T47D cells.
研究领域:
有机化学
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药物化学
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癌症研究
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DOI
PubMed
高影响因子
ACTA PHARMACOLOGICA SINICA
·
2024
·
IF 6.9
Hu You-tian,Liu Zhi-wei,Zhang Tong-hui,Ma Yu-e,He Lei,Zhang Jie,Zhou Yue-yang,Vidal-Puig Antonio,Pan De-jing,Wu Fang
Thymic egress is a crucial process for thymocyte maturation, strictly regulated by sphingosine-1-phosphate lyase (S1PL). Recently, cystathionine γ-lyase (CSE), one of the enzymes producing hydrogen sulfide (H 2 S), has emerged as a vital immune process regulator. However, the molecular connection between CSE, H 2 S and thymic egress remains largely unexplored. In this study, we investigated the regulatory function of CSE in the thymic egress of immune cells. We showed that genetic knockout of CSE or pharmacological inhibition by CSE enzyme inhibitor NSC4056 or D , L -propargylglycine (PAG) significantly enhanced the migration of mature lymphocytes and monocytes from the thymus to the peripheral blood, and this redistribution effect could be reversed by treatment with NaHS, an exogenous donor of H 2 S. In addition, the CSE-generated H 2 S significantly increased the levels of S1P in the peripheral blood, thymus and spleen of mice, suppressed the production of proinflammatory cytokines and rescued pathogen-induced sepsis in cells and in vivo. Notably, H 2 S or polysulfide inhibited S1PL activity in cells and an in vitro purified enzyme assay. We found that this inhibition relied on a newly identified C 203 XC 205 redox motif adjacent to the enzyme’s active site, shedding light on the biochemical mechanism of S1PL regulation. In conclusion, this study uncovers a new function and mechanism for CSE-derived H 2 S in thymic egress and provides a potential drug target for treating S1P-related immune diseases.
研究领域:
免疫学
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生物化学
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药理学
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DOI
PubMed
高影响因子
CHINESE JOURNAL OF POLYMER SCIENCE
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2019
·Vol. 38
·期 1
·72-83
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IF 2.804
Han Yue,Tang Dong-Hao,Wang Guang-Xing,Sun Ya-Nan,Guo Ying,Zhou Heng,Qiu Wen-Feng,Zhao Tong
Vanillin was used as sustainable source for phthalonitrile monomer synthesis, and allyl/propargyl ether moieties were introduced to improve the processability at the minimal cost of thermal properties. The synthesis route was optimized to minimize side-reactions and simplify post-processing, and the monomers were obtained in high purity and good yields. The curing behavior, mechanism, and processability of the monomers were studied, and the thermal properties of cured polymers were evaluated. Of the two monomers, the allyl ether-containing one exhibited a wide processing window of 185 °C, and was mainly cured into phthalocyanine and linear aliphatic structures through self-catalytic curing process. Also, the glass transition temperature was higher than 500 °C. In contrast, the propargyl ether-containing monomer could only be partially cured, and heat resistance was found to be compromised. Compared with traditional petroleum-based phthalonitrile resins, the bio-based monomers could be cured without the addition of catalysts, and improvement in processability was achieved at no cost of thermal performances.
研究领域:
材料科学
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高分子化学
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可持续材料
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有机化学
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产品关联
DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
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2019
·
IF 4.745
Shou-Jie Shen,Xiao-Li Du,Xiao-Li Xu,Ming-Gang Zhao,Jin-Yan Liang
The regioselective N-addition/substitution reaction between α-alkylidene pyrazolinones and propargyl sulfonium salts has been developed to construct functionalized allylthio-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones act as N-nucleophilic agents which are distinguished from reported C-nucleophilic reactions. Excellent regioselectivity, readily available starting materials, the broad range of substrates, gram-scale synthesis, and simple operation illustrate the synthetic advantages of this new reaction pathway.
研究领域:
有机化学
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合成化学
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杂环化学
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产品关联
DOI
PubMed
高影响因子
RSC Advances
·
2019
·Vol. 9
·期 60
·34912-34925
·
IF 3.049
Shou-Jie Shen,Xiao-Li Du,Xiao-Li Xu,Yue-Hua Wu,Ming-gang Zhao,Jin-Yan Liang
The first sequentially combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones function as N-nucleophilic agents distinguished from the reported C-addition reactions. Propargyl sulfonium salts were first involved in the [2,3]-sigmatropic rearrangement protocol differentiated from the well-established annulation reactions. The excellent regioselectivity, the broad scope of substrates, gram-scale synthesis and convenient transformation embody the synthetic superiority of this cascade process.
研究领域:
有机化学
·
合成化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2017
·
IF 3.671
Ling Yi,Yisi Wang,Guanliang Lin,Danling Lin,Wenliang Chen,Yugang Huang,Guodong Ye
Ring-opening polymerization of S -propargyl-cysteine -N -carboxyanhydride has been used to synthesize conformation switchable poly( S -propargyl-cysteine) starting with l -cysteine, d l - and d -cysteine. Then cationic polypeptides with different backbone chirality are obtained by nearly 100% side-chain grafting of cysteamine via thiol-yne click chemistry. The cationic polypeptides containing mixed conformations of β-sheets, β-turns and random coils are stable against pH, salt and temperature variations. The cationic polypeptides can condense siRNA at a low polypeptide/siRNA weight ratio to form nanoparticles with size depending on the backbone chirality. The cationic polypeptides derived from poly( S -propargyl- l or d -cysteine) are non-cytotoxic to HeLa and HepG2 cells, but interrupting the backbone chirality enhances the cytotoxicity sharply. The cationic polypeptides used for siRNA delivery show good transfection efficiency, but cell internalization process depends on the backbone chirality. The cationic polypeptide derived from the poly( S -propargyl- l -cysteine) is an appropriate siRNA vector with advantages of non-cytotoxicity and high transfection efficiency.
研究领域:
高分子化学
·
纳米技术
·
生物医学工程
·
分子生物学
·
药学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）