14631-20-0Relevant articles and documents
Synthesis, physicochemical characteristics, and biocompatibility of self-assemble polymers bearing guanine, cytosine, uracil, and thymine moieties
Kim, Jin Chul,Kim, Mihee,Jung, Jungwoon,Lee, Jinseok,Ree, Brian J.,Kim, Heesoo,Kim, Ik Jung,Kim, Jung Ran,Ree, Moonhor
, p. 1151 - 1160 (2015)
We synthesized chemically well-defined brush (i.e., comb-like) polymers bearing guanine, cytosine, uracil, or thymine moieties at the bristle ends. The polymers were stable up to 220 °C and were readily solution-processable, yielding high-quality films. Interestingly, the brush polymers favorably self-assembled to form molecular multibilayer structures stabilized by hydrogen bonding interactions among the nucleobase moieties at the bristle ends, which provided nucleobase-rich surfaces. The multibilayer-structured polymer films showed high water affinity. They also displayed selective protein adsorption, suppressed bacterial adherence, facilitated cell adhesion, and exhibited good biocompatibility in mice. The brush polymer DNA-mimicking comb-like polymers are suitable as biomaterials and in protein separation applications.
Synthesis of N4-β-D-glycoside cytosines and sugar N 4-acetylcytosin-1-ylmethylhydrazones as antiviral agents
Ali, Omar M.,Amer, Hamada H.,Abdel-Rahman, Adel A.-H.
, p. 281 - 283 (2007)
Reaction of monosaccharide aldoses with cytosine (1) gave stereoselectively β-N-glycosides 2a-d, which were treated with acetic anhydride in pyridine to afford the corresponding acetylated derivatives 3a-d. N4- Acetylcytosine (4) was synthesised and treated with ethyl chloroacetatete give 1-(ethoxycarbonylmethy)-N4-acetylcytosine (5). Hydrolysis of the latter ester with hydrazine hydrate afforded the hydrazide derivative 6. Condensation of the hydrazide with monosaccharide aldoses gave the corresponding sugar hydrazones 7a-f. Acetylation of the hydrazones afforded the per-O-acetyl derivatives 8a-f. The prepared compounds were tested for antiviral activity against hepatitis B virus (HBV) which showed moderate activities.
N -Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides
Beau, Jean-Marie,Beretta, Margaux,Dr?ge, Thomas,Es-Sayed, Mazen,Nicolas, Lionel,Norsikian, Stéphanie,Rouchaud, Emilie,Vors, Jean-Pierre
supporting information, p. 4285 - 4291 (2021/05/31)
The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields.
Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine
Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei
, p. 1203 - 1213 (2019/01/29)
Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.
