13964-23-3Relevant academic research and scientific papers
Design And Synthesis Of An Azabicyclic Nucleoside Phosphoramidite For Oligonucleotide Antisense Constructs
Salinas, Juan C.,Seth, Punit P.,Hanessian, Stephen
, p. 384 - 406 (2020)
We report the synthesis and biophysical evaluation of an azabicycle dinucleotide with restricted γ, β, and ε torsion angles, featuring the introduction of a piperidine ring that locks the conformation of the nucleoside into an RNA-type nucleic acid. The c
3-Azidoazetidines as the first scaffolds for β-amino azetidine carboxylic acid peptidomimetics: azetidine iminosugars containing an acetamido group do not inhibit β-N-acetylhexosaminidases
Liu, Zilei,Jenkinson, Sarah F.,Kato, Atsushi,Nakagawa, Shinpei,Wormald, Mark R.,Yu, Chu-Yi,Fleet, George W.J.
, p. 872 - 881 (2016)
Stable amides and oligopeptides derived from methyl trans,trans-3-azido-4-hydroxymethyl-L-azetidine carboxylate, prepared in 19% yield from diacetone allose, is the first example of a β-amino-azetidine carboxylic acid incorporated into peptidomimetics and provides a scaffold for investigating secondary structure induced by a novel β-amino acid. A number of azetidine iminosugars containing a NHAc substituent were prepared but none of them were β-N-acetylhexosaminidase inhibitors.
An efficient method to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides
Wang, A-Peng,Liu, Chao,Yang, Shuang,Zhao, Zhehui,Lei, Pingsheng
, p. 285 - 297 (2016)
A new and facile procedure was developed to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Seven trichloroacetimidate donors which had different types of substituent groups at C-6 position were synthesized to couple with the erythronolide. Nine novel 5-O-(6′-modified)-mycaminose 14-membered ketolides were obtained to verify the utility of the method.
Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation
Sert, Mustafa,I??lar, ?zer,Yaglioglu, Ayse Sahin,Bulut, Adnan
, (2021/09/07)
N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NM
Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone
Arat, Esra,Bulut, Adnan,Demirta?, ?brahim,I??lar, ?zer,Sahin Yaglioglu, Ayse,Türk, Mustafa
, (2020/04/08)
A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.
Multicomponent Approach to Homo-and Hetero-Multivalent Glycomimetics Bearing Rare Monosaccharides
Jakas, Andreja,Jeri?, Ivanka,Vi?njevac, Aleksandar
, p. 3766 - 3787 (2020/03/30)
We applied a multicomponent approach to access a library of densely functionalized homo-and hetero-multivalent glycomimetics comprising aldehyde, amine, and isocyanide components related to isopropylidene-protected d-fructose, l-sorbose, d-galactose, and d-Allose. Passerini products were obtained in very good yields (up to 78%) and high diastereoselectivities (up to 98:2). Three types of products were obtained by the Ugi reaction; along with the "classical" four-component product, α-Acylaminoamides, a three-component α-Aminoamides, and a four-component α-Aminoacylamides were isolated. The presence of multiple pathways is rationalized by the structure of the imidate intermediate, mainly influenced by the amine component.
A method for preparing N-alkylated kanosamines from diacetone D-glucose
Cannone, Zachary P.,Peczuh, Mark W.
, p. 1830 - 1833 (2019/06/19)
The aminoglycoside (AG) antibiotics have seen a resurgence in their clinical use given the increase in multi drug resistant bacterial infections. Campaigns to generate novel analogs show promise that structural modification can lead to compounds with improved pharmacological properties. The results described herein include a new method to synthesize mono-, di-, and mixed N-alkylated kanosamine sugars and their elaboration into novel glycosides that inhibit bacterial protein synthesis in vitro.
Cluster glycosides and heteroglycoclusters presented in alternative arrangements
Figueredo, Andreza S.,Zamoner, Luis O.B.,Rejzek, Martin,Field, Robert A.,Carvalho, Ivone
, p. 4405 - 4409 (2018/11/10)
Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose
Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity
Halay, Erkan,Ay, Emriye,?alva, Emine,Ay, Kadir,Karay?ld?r?m, Tamer
, p. 158 - 166 (2018/04/02)
[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.
C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies
Nagy, Adrienn,Csordás, Barbara,Zsoldos-Mády, Virág,Pintér, István,Farkas, Viktor,Perczel, András
, p. 223 - 240 (2017/02/05)
To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.
