7362-93-8Relevant articles and documents
Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides
Ma?a, Patrycja,Pedersen, Christian Marcus
supporting information, p. 5685 - 5689 (2021/08/30)
N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.
Multifunctional polymeric micelle for jointly conveying photosensitizer and gene editing system, preparation method of micelle and application of micelle
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Paragraph 0069; 0078-0079, (2020/03/09)
The invention discloses a multifunctional polymeric micelle for jointly conveying a photosensitizer and a gene editing system, a preparation method of the micelle and an application of the micelle. The multifunctional polymeric micelle is of a three-layer structure, a core is hydrophobic polycaprolactone for loading the photosensitizer, a middle layer is ligand NTA (nitrilotriacetic acid) which can be coupled with the gene editing system, and an outer layer is an iRGD-polyethylene glycol-polyaspartyl (butanediamine) positive polymer and can be combined with the middle layer through electrostatic interaction. The multifunctional polymer serves as a carrier, and can efficiently enter a tumor cell owing to targeting ability after loading the photosensitizer and the gene editing system, the micelle and the gene editing system are dissociated in a lysosome acid environment, the photosensitizer realizes photodynamic therapy after laser irradiation, the gene editing system knocks out expressed genes of Nrf2 and blocks expression of the Nrf2, and apoptosis of the tumor cell is promoted. The photosensitizer and the gene editing system jointly play a role, photodynamic therapy and gene therapy are simultaneously performed, and antitumor effects are greatly enhanced.
Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates
Zhao, Ming,Bi, Lanrong,Wang, Wei,Wang, Chao,Baudy-Floc'h, Michele,Ju, Jingfang,Peng, Shiqi
, p. 6998 - 7010 (2007/10/03)
β-Carboline represents a class of compounds with potent anti-tumor activity by intercalating with DNA. To further enhance the cytotoxic potency and bioavailability of β-carboline, a series of novel β-carboline amino acid ester conjugates were designed and synthesized, and the cytotoxic activities of these compounds were tested using a panel of human tumor cell lines. In addition, the membrane permeability of these compounds was evaluated in vitro using a Caco-2 cell monolayer model. The β-carboline amino acid ester conjugates demonstrated improved cytotoxic activity compared to the parental β-carbolines. In particular, the Lys/Arg conjugates were the most potent analogs with an IC50 value of 4 and 1 μM against human cervical carcinoma cells. The low interaction energy of Arg conjugate based on molecular modeling may contribute to its enhanced cytotoxicity. Taken together, this study provided new insights into structure-activity relationships in the β-carboline amino acid ester conjugates and identified the β-carboline Lys/Arg conjugates as promising lead compounds for further in vivo biological and molecular evaluation.
Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers
Li, Bryan,Berliner, Martin,Buzon, Richard,Chiu, Charles K.-F.,Colgan, Stephen T.,Kaneko, Takushi,Keene, Nandell,Kissel, William,Le, Tung,Leeman, Kyle R.,Marquez, Brian,Morris, Ronald,Newell, Lisa,Wunderwald, Silke,Witt, Michael,Weaver, John,Zhang, Zhijun,Zhang, Zhongli
, p. 9045 - 9050 (2007/10/03)
(Chemical Equation Presented) Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative 4, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.
Aqueous phosphoric acid as a mild reagent for deprotection of the t-butoxycarbonyl group
Li, Bryan,Bemish, Raymond,Buzon, Richard A.,Chiu, Charles K.-F.,Colgan, Stephen T.,Kissel, William,Le, Tung,Leeman, Kyle R.,Newell, Lisa,Roth, Joshua
, p. 8113 - 8115 (2007/10/03)
Aqueous phosphoric acid (85 wt%) is an efficient and mild reagent for the deprotection of N-BOC groups. Acid sensitive functionalities including benzyl and methyl esters, TBDMS ether, CBZ and isopropylidene groups are compatible with the reaction conditions. The reactions are high yielding, and the workup is convenient.
