51699-45-7Relevant academic research and scientific papers
Phosphoryl N - fatty acyl nucleoside analogues for treatment of viral hepatitis and liver cancer
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Paragraph 0033-0036; 0041-0042, (2020/07/13)
The invention discloses a phosphoryl N-fatty acyl nucleoside analogue for treating viral hepatitis and liver cancer. The phosphoryl N-fatty acyl nucleoside analogue is characterized in that a nucleoside analogue is modified by a cyclophosphoryl group and
Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent
Gieuw, Matthew H.,Ke, Zhihai,Yeung, Ying-Yeung
supporting information, p. 3782 - 3786 (2018/03/13)
A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.
Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2α and cytotoxicity properties
Borowiecki, Pawe?,Wawro, Adam M.,Wińska, Patrycja,Wielechowska, Monika,Bretner, Maria
supporting information, p. 364 - 374 (2014/08/05)
The efficient method for the synthesis of novel 4,5,6,7-tetrabromo-1H- benzotriazole (TBBt) derivatives bearing a single stereogenic center has been developed. New compounds with a variety of substituents at the meta- and para-position of the phenyl ring are reported. All of the presented compounds were obtained using classical synthetic methods, such as bromination of benzotriazole, and its subsequent alkylation by monotosylated arylpropane-1,3-diols, which in turn have been synthesized through reduction of the corresponding prochiral β-keto esters, and the selective monotosylation of the primary hydroxyl group. The influence of the new and previously reported N-hydroxyalkyl TBBt derivatives on the activity of human protein kinase CK2α catalytic subunit was examined. The most active were derivatives with N-hydroxyalkyl substituents (IC50 in 0.80-7.35 μM range). A binding mode of (R)-1-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)butan-3-ol 7b to hCK2α has been proposed based on in silico docking studies. Additionally, MTT-based cytotoxicity tests demonstrated high activities of novel 1-aryl-3-TBBt-propan-1-ol and 3-TBBt-propan-1,2-diol derivatives against human peripheral blood T lymphoblast (CCRF-CEM), and moderate anti-tumor activities against human breast adenocarcinoma (MCF7) cell lines.
Design, synthesis, and evaluation of novel cyclic phosphates of 5-aminosalicylic acid as cytochrome P450-activated prodrugs
Huttunen, Kristiina M.,Tani, Niina,Juvonen, Risto O.,Raunio, Hannu,Rautio, Jarkko
, p. 532 - 537 (2013/08/24)
Four novel cyclic phosphates of the anti-inflammatory agent 5-aminosalicylic acid (5-ASA) were designed and synthesized as cytochrome P450 (CYP)-activated prodrugs. These prodrugs can be used for targeting into gut wall, since these types of cyclic phosph
Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: The influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications
Borowiecki, Pawel,Bretner, Maria
, p. 925 - 936 (2013/09/23)
Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.
Design, Synthesis, and Sustained-Release Property of 1,3-Cyclic Propanyl Phosphate Ester of 18β-Glycyrrhetinic Acid
Sun, Weizhi,Peng, Weibing,Li, Guoqiang,Jiang, Tao
experimental part, p. 206 - 211 (2012/02/01)
A new class of potential prodrugs, 1,3-cyclic propanyl phosphate esters of 18β-glycyrrhetic acid, was designed and synthesized through the key reaction of 18β-glycyrrhetic acid with 1,3-cyclic propanyl phosphate ester catalysed by lithium diisopropylamide
Tandem catalysis by lipase in a vinyl acetate-mediated cross-aldol reaction
Kumar, Manjeet,Shah, Bhahwal A.,Taneja, Subhash C.
experimental part, p. 1207 - 1212 (2011/06/25)
The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate-mediated aldol reaction. The reaction was facilitated through the lipase-catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal side product formation.
Pradefovir: A prodrug that targets adefovir to the liver for the treatment of hepatitis B
Reddy, K. Raja,Matelich, Michael C.,Ugarkar, Bheemarao G.,Gómez-Galeno, Jorge E.,DaRe, Jay,Ollis, Kristin,Sun, Zhili,Craigo, William,Colby, Timothy J.,Fujitaki, James M.,Boyer, Serge H.,Van Poelje, Paul D.,Erion, Mark D.
, p. 666 - 676 (2008/09/19)
Adefovir dipivoxil, a marketed drug for the treatment of hepatitis B, is dosed at submaximally efficacious doses because of renal toxicity. In an effort to improve the therapeutic index of adefovir, 1-aryl-1,3-propanyl prodrugs were synthesized with the r
Phosphoramidate and phosphate prodrugs of (-)-β-D-(2R,4R)-dioxolane- thymine: Synthesis, anti-HIV activity and stability studies
Liang, Yuzeng,Narayanasamy, Janarthanan,Schinazi, Raymond F.,Chu, Chung K.
, p. 2178 - 2189 (2007/10/03)
A series of phosphoramidate and phosphate prodrugs of DOT were synthesized via dichlorophosphate or H-phosphonate chemistry and evaluated for their anti-HIV activity against LAI M184V mutants in PBM cells as well as for their cytotoxicity. The antiviral and cytotoxic profiles of the prodrugs were compared with that of the parent compound (DOT), and it was found that four aryl phosphoramidates 5, 18, 20, and 26 showed a significant enhancement (8- to 12-fold) in anti-HIV activity without cytotoxicity. Chemical stability of these prodrugs was evaluated in phosphate buffer at pH values of biological relevance (i.e., pH 2.0 and 7.4). Enzymatic hydrolysis was also studied in esterase or lipase in buffer solution. Chemical stability studies indicate that the phosphoramidates have good chemical stability at pH 2.0 and at pH 7.4 phosphate buffer. Phosphoramidate prodrugs were hydrolyzed in vitro by esterase or lipase and found to be better substrates for lipases than for esterases. 1,3-Diol cyclic phosphates showed potent anti-HIV activity without increasing the cytotoxicity compared with that of DOT and have good chemical and enzymatic stability. Long-chain lipid phosphates, although showed potent anti-HIV activity, exhibited increased cytotoxicity.
Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-β-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma
Boyer, Serge H.,Sun, Zhili,Jiang, Hongjian,Esterbrook, Julie,Gómez-Galeno, Jorge E.,Craigo, William,Reddy, K. Raja,Ugarkar, Bheemarao G.,MacKenna, Deidre A.,Erion, Mark D.
, p. 7711 - 7720 (2007/10/03)
Cytotoxic nucleosides have proven to be ineffective for the treatment of hepatocellular carcinoma (HCC) due, in part, to their inadequate conversion to their active nucleoside triphosphates (NTP) in the liver tumor and high conversion in other tissues. Th
