功能糖化合物的合成及活性研究；硅氧烷体系还原缩醛及羰基衍生物
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摘要
第一部分：通过“点击化学”合成手段,高效制备了系列糖功能化合物,其中大部分具有良好的生物活性或光电活性。
◆苯二酰胺或苯二酸酯基团桥联的三氮唑芳香糖衍生物通过Cu+催化的叠氮-炔环加成反应(点击化学)制备,发现8个化合物对蛋白酪氨酸磷酸酯酶1B (PTP-1B)具备微摩尔级别的抑制活性,并对同族PTP酶有多倍选择性。半乳糖、葡萄糖、甘露糖衍生物表现出不同的的生物活性,推测是由单糖的差向异构效应引起。
◆通过点击化学合成芳香糖水杨酸类似物,同时靶向PTP-1B的催化位点和周边位点,设计用不同长度的脂肪碳链桥联羟基苯甲酸衍生物与芳香糖。2个化合物对PTP-1B有微摩尔级的抑制活性,并对同源酶TCPTP、SHP-1、SHP-2和LAR有选择性。计算机模拟了PTP-1B酶与抑制剂结合的模式。
◆通过点击化学高效地制备三氮唑乙酰糖基蒽醌化合物59。在微量Cu2+的存在下,59在紫外-可见光检测中发生明显蓝移,吸收度大大增强；同时59的荧光淬灭。这种现象推测由分子内电荷转移引起。比起其它金属离子,Cu2+表现出很强的选择性。根据荧光离子滴定和核磁共振滴定推测,配体-离子络合物以2：1的模式结合。Cu2+的存在还显著改变了59的电化学信号,说明59是光电两性分子探针。
第二部分：在有机还原反应中,常使用硼、铝氢化物还原有机官能团,但这些还原剂较危险,反应条件剧烈,并产生过量无机盐。根据“绿色化学”原则,发展安全、廉价的硅工业副产物硅氧烷1,1,3,3-四甲基二硅氧烷(TMDS)高效、选择性地还原了多类有机官能团。TMDS在反应结束后生成的硅化合物可回收用作疏水材料。
◆本研究工作发展了还原脂肪、芳香缩醛成醚的方法。反应由三氟甲磺酸铋Bi(OTf)3或Cu(OTf)2催化,在室温条件下高效制备目标化合物。在还原缩醛底物时不影响羟基、硝基、芳香环、酯和腈基。这种方法仅用少量的还原试剂TMDS和催化剂,原子经济性优势明显,同时避免使用Pd-C等昂贵的金属还原剂。
TMDS和Cu(OTf)2或AICl3-一起使用,可选择性地将吡喃糖4,6-0-缩醛开环,得到4位醚或6位醚。此方法兼容葡萄糖苷、半乳糖苷、甘露糖苷,苄基、酰基等保护基团,还可直接有效还原存在裸露羟基的糖缩醛。长碳链糖醚可通过这种方法被简便地制备,该类化合物具有表面活性和抗菌活性。
TMDS和催化量的Cu(OTf)2可高产率、高选择性地一步将脂肪、芳香羧酸还原成伯醇,解决了其它方法使用过量、危险还原剂,需两步反应或无法有效还原芳香羧酸的局限。TMDS/Cu(OTf)2体系同时可在温和反应条件下将醛、酮转化成对称醚,成为Williamson醚化的一种替代方法。
Part1:We take advantage of the merits of sugar to develop products with good properties via efficient synthetic methods including "Click Chemistry".
Dimeric and monomeric benzylated glycosyl benzenes were prepared through copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). These products were identified as inhibitors of protein tyrosine phosphatase1B (PTP-1B), which showed at least several fold selectivity over other homologous PTPases. The galactosyl, glucosyl and mannosyl inhibitors displayed different biological properties, so the monosaccharides may be used as chiral scaffolds to probe the spatial preference of PTP-1B.
To develop new PTP-1B inhibitors based on sugar structures, a library of benzyl6-triazolo(hydroxy)benzoic glucosides was constructed through copper(Ⅰ)-catalyzed azide-alkyne cycloaddition. Between the (hydroxy)-benzoic moieties and carbohydrate, these glycoconjugates bear aliphatic chain length-varied bridges. They were identified as PTP-1B inhibitors with selectivity over TCPTP, SHP-1, SHP-2and LAR. The plausible binding modes of these sugar-based inhibitors with PTP-1B were then elaborated by molecular docking study.
A new triazole-linked acetyl-glucosyl anthraquinone59was synthesized via straightforward click chemistry. The glycoconjugate59displayed an obvious quenching fluorescence and blue shift absorption in the presence of trace amounts of Cu2+. It is presumably due to intramolecular charge transfer (ICT), which also exhibited high selectivity over a panel of other cations tested in MeCN. It is suggested by the result of fluorescence spectroscopy titration that a2:1ligand-to-cation complex was formed, which was also reflected via NMR spectroscopy titration. Furthermore, the addition of Cu2+to59remarkably changed its electrochemical behavior, which was demonstrated by differential pulse voltammetry (DPV) measurements.
Part2:In compliance with the principles of Green Chemistry, we developed several methodologies to reduce various organic functional groups efficiently and selectively. A safe and cheap siloxane1,1,3,3-tetramethyldisiloxane (TMDS) was employed.
A protocol is shown for the reduction of aliphatic and aromatic acetals to ethers, which was catalyzed by Bi(OTf)3or Cu(OTf)2in excellent yields at room temperature, without affecting hydroxyl groups, nitrile, aromatic rings, ester and nitro groups. This system makes an improvement concerning atom economy in comparison with the previous methods, by remarkably decreasing the quantity of the reducing reagent TMDS, and using a relatively small amount of catalyst.
TMDS was developed as an excellent dual-purpose reducing reagent for the regioselective ring opening of a series of hexopyranosyl4,6-O-acetals in the presence of Cu(OTf)2or AICl3, leading to the corresponding primary or secondary ethers. Its application to the convenient preparation of carbohydrate-based long alkyl chain ethers is highlighted.
A reagent system is described for the reduction of carboxylic acids to the corresponding primary alcohols using TMDS and a catalytic quantity of Cu(OTf)2. Alkyl and aromatic carboxylic acids are reduced in good yields and high selectivity. TMDS/Cu(OTf)2protocol has also been demonstrated to be very efficient in the synthesis of symmetrical ethers from aldehydes and ketones under mild conditions.
◆苯二酰胺或苯二酸酯基团桥联的三氮唑芳香糖衍生物通过Cu+催化的叠氮-炔环加成反应(点击化学)制备,发现8个化合物对蛋白酪氨酸磷酸酯酶1B (PTP-1B)具备微摩尔级别的抑制活性,并对同族PTP酶有多倍选择性。半乳糖、葡萄糖、甘露糖衍生物表现出不同的的生物活性,推测是由单糖的差向异构效应引起。
◆通过点击化学合成芳香糖水杨酸类似物,同时靶向PTP-1B的催化位点和周边位点,设计用不同长度的脂肪碳链桥联羟基苯甲酸衍生物与芳香糖。2个化合物对PTP-1B有微摩尔级的抑制活性,并对同源酶TCPTP、SHP-1、SHP-2和LAR有选择性。计算机模拟了PTP-1B酶与抑制剂结合的模式。
◆通过点击化学高效地制备三氮唑乙酰糖基蒽醌化合物59。在微量Cu2+的存在下,59在紫外-可见光检测中发生明显蓝移,吸收度大大增强；同时59的荧光淬灭。这种现象推测由分子内电荷转移引起。比起其它金属离子,Cu2+表现出很强的选择性。根据荧光离子滴定和核磁共振滴定推测,配体-离子络合物以2：1的模式结合。Cu2+的存在还显著改变了59的电化学信号,说明59是光电两性分子探针。
第二部分：在有机还原反应中,常使用硼、铝氢化物还原有机官能团,但这些还原剂较危险,反应条件剧烈,并产生过量无机盐。根据“绿色化学”原则,发展安全、廉价的硅工业副产物硅氧烷1,1,3,3-四甲基二硅氧烷(TMDS)高效、选择性地还原了多类有机官能团。TMDS在反应结束后生成的硅化合物可回收用作疏水材料。
◆本研究工作发展了还原脂肪、芳香缩醛成醚的方法。反应由三氟甲磺酸铋Bi(OTf)3或Cu(OTf)2催化,在室温条件下高效制备目标化合物。在还原缩醛底物时不影响羟基、硝基、芳香环、酯和腈基。这种方法仅用少量的还原试剂TMDS和催化剂,原子经济性优势明显,同时避免使用Pd-C等昂贵的金属还原剂。
TMDS和Cu(OTf)2或AICl3-一起使用,可选择性地将吡喃糖4,6-0-缩醛开环,得到4位醚或6位醚。此方法兼容葡萄糖苷、半乳糖苷、甘露糖苷,苄基、酰基等保护基团,还可直接有效还原存在裸露羟基的糖缩醛。长碳链糖醚可通过这种方法被简便地制备,该类化合物具有表面活性和抗菌活性。
TMDS和催化量的Cu(OTf)2可高产率、高选择性地一步将脂肪、芳香羧酸还原成伯醇,解决了其它方法使用过量、危险还原剂,需两步反应或无法有效还原芳香羧酸的局限。TMDS/Cu(OTf)2体系同时可在温和反应条件下将醛、酮转化成对称醚,成为Williamson醚化的一种替代方法。
Part1:We take advantage of the merits of sugar to develop products with good properties via efficient synthetic methods including "Click Chemistry".
Dimeric and monomeric benzylated glycosyl benzenes were prepared through copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). These products were identified as inhibitors of protein tyrosine phosphatase1B (PTP-1B), which showed at least several fold selectivity over other homologous PTPases. The galactosyl, glucosyl and mannosyl inhibitors displayed different biological properties, so the monosaccharides may be used as chiral scaffolds to probe the spatial preference of PTP-1B.
To develop new PTP-1B inhibitors based on sugar structures, a library of benzyl6-triazolo(hydroxy)benzoic glucosides was constructed through copper(Ⅰ)-catalyzed azide-alkyne cycloaddition. Between the (hydroxy)-benzoic moieties and carbohydrate, these glycoconjugates bear aliphatic chain length-varied bridges. They were identified as PTP-1B inhibitors with selectivity over TCPTP, SHP-1, SHP-2and LAR. The plausible binding modes of these sugar-based inhibitors with PTP-1B were then elaborated by molecular docking study.
A new triazole-linked acetyl-glucosyl anthraquinone59was synthesized via straightforward click chemistry. The glycoconjugate59displayed an obvious quenching fluorescence and blue shift absorption in the presence of trace amounts of Cu2+. It is presumably due to intramolecular charge transfer (ICT), which also exhibited high selectivity over a panel of other cations tested in MeCN. It is suggested by the result of fluorescence spectroscopy titration that a2:1ligand-to-cation complex was formed, which was also reflected via NMR spectroscopy titration. Furthermore, the addition of Cu2+to59remarkably changed its electrochemical behavior, which was demonstrated by differential pulse voltammetry (DPV) measurements.
Part2:In compliance with the principles of Green Chemistry, we developed several methodologies to reduce various organic functional groups efficiently and selectively. A safe and cheap siloxane1,1,3,3-tetramethyldisiloxane (TMDS) was employed.
A protocol is shown for the reduction of aliphatic and aromatic acetals to ethers, which was catalyzed by Bi(OTf)3or Cu(OTf)2in excellent yields at room temperature, without affecting hydroxyl groups, nitrile, aromatic rings, ester and nitro groups. This system makes an improvement concerning atom economy in comparison with the previous methods, by remarkably decreasing the quantity of the reducing reagent TMDS, and using a relatively small amount of catalyst.
TMDS was developed as an excellent dual-purpose reducing reagent for the regioselective ring opening of a series of hexopyranosyl4,6-O-acetals in the presence of Cu(OTf)2or AICl3, leading to the corresponding primary or secondary ethers. Its application to the convenient preparation of carbohydrate-based long alkyl chain ethers is highlighted.
A reagent system is described for the reduction of carboxylic acids to the corresponding primary alcohols using TMDS and a catalytic quantity of Cu(OTf)2. Alkyl and aromatic carboxylic acids are reduced in good yields and high selectivity. TMDS/Cu(OTf)2protocol has also been demonstrated to be very efficient in the synthesis of symmetrical ethers from aldehydes and ketones under mild conditions.
引文
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