4594-52-9Relevant articles and documents
X-ray structure of 1,3,4-tri-O-acetyl-2-deoxy-β-d-erythro-pentopyranose
Chen, Ji-Jun,Gao, Jian-Rong,Han, Liang,Jia, Jian-Hong,Sheng, Wei-Jian,Li, Yu-Jing
, p. 2056 - 2059 (2009)
Peracetylated 2-deoxy-d-erythro-pentose (2-deoxy-d-ribose) was synthesized through the acetylation of 2-deoxy-d-ribose with acetic anhydride in pyridine, and the products (including all four ring forms) exist in form of either a white solid or a syrup. A
SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG
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Page/Page column 6-7; 13, (2021/05/29)
The invention is a drug for anticancer and antiviral therapy, comprising a nucleoside analogue (7) comprising a furan ring irreversibly bound to the RNA/DNA synthesis chain by phosphodiester bonds and having SP3 hybridization, and folic acid (A) bound to the nucleoside analogue (7) comprising furan ring. The synthesis method of the said nucleoside analogue is also contained within the scope of the invention. In this work, a nucleoside-analogue was transformed after converting the furan-ring hybridization from Sp2 to Sp3 to make it more selectivity with different enzymes and linking it via site 5 with the effective folic acid towards entering the substances inside the cells and to become the final compound possessing anti-cancer and anti- virus properties after controlling the replication and reproduction process in DNA.
Method for synthesizing decitabine key intermediate by solid acid catalysis
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Paragraph 0036-0038, (2020/08/06)
The invention belongs to the technical field of medicinal chemistry, and relates to a method for synthesizing a decitabine key intermediate (formula II) by solid acid catalysis. The method is characterized in that silicon dioxide loaded stannic chloride (SnCl4) is used as a catalyst for glycosylation reaction. The method has the advantages that the problem of complicated post treatment of a liquidacid catalyst is solved, and the content of beta-configuration intermediate can be effectively improved.
First characterisation of two important postulated intermediates in the formation of a HydT DNA lesion, a thymidine oxidation product
Psykarakis, Emmanuel E.,Chatzopoulou, Elli,Gimisis, Thanasis
, p. 2289 - 2300 (2018/04/05)
A number of environmental pollutants and endogenous oxidation agents form 1-(2-deoxy-β-d-ribofuranosyl)-5-hydroxy-5-methylhydantoin (HydT), an important DNA lesion resulting from thymidine oxidation. In this paper, two intermediates, postulated in the formation of HydT, have been characterised for the first time. The first, N1-formyl-N3-pyruvoylurea intermediate, was produced by the ozonolysis reaction of 2′,3′,5′-tri-O-acetylribo-, 3′,5′-di-O-TBS- and N3,O3′,O5-tribenzyl-protected thymidines and was shown to produce, upon decomposition and depending on the protecting group and the conditions, HydT alone, or together with protected-β-d-ribofuranosyl-N1-formylurea and formamide products. In addition, the second and long sought, open-chain-pyruvoylurea intermediate, was produced through de novo synthesis in protected β-d-ribofuranosyl-, 2-deoxy-β-d-ribofuranosyl- and 2-deoxy-β-d-ribopyranosyl systems. The conditions that induce the cyclization to the hydantoin ring of HydT have been determined. The chemistry utilised in the de novo synthesis is suitable for generating isotopically labelled HydT, as a reference in isotope-dilution-aided quantification of DNA damage.
Synthesis of 2-deoxy ribose related disaccharide nucleoside and its phosphoramidite
Ding, Yili,Deng, Rilie,Wang, Bingyun
, p. 3848 - 3852 (2017/06/13)
Synthesis of impurity reference compound of anti-tumor drug ISIS 183750 was achieved. In this process, a general method for synthesis of 2-deoxy ribosyl disaccharide nucleosides was established for the first time.
Sono-transition-metal catalysis of one-pot three-step synthesis of glycosyl-1,2,3-triazoles
Driowya, Mohsine,Bougrin, Khalid,Benhida, Rachid
supporting information, p. 1808 - 1817 (2013/05/22)
As a continuation of our studies directed at the development of straightforward and sustainable methodologies, we describe herein an original example of a combined effect of ultrasonic activation and iron-copper dual catalysis that allows an efficient and ecofriendly one-pot, three-step route to a new series of nucleoside-substituted triazoles. The reactions were carried out under both conventional and ultrasonic irradiation conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
PROCESS FOR THE PREPARATION OF (2R.3S)-2-(HYDROXYMETHYL) -5-METHOXYTETRAHYDROFURAN-3-OL AND ACETYLATED DERIVATIVES THEREOF, FREE OF PYRANOSE COMPOUNDS
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, (2012/06/15)
A method of preparing a ribofuranose derivative essentially free of pyranose compounds includes a step of contacting a solution of MDR containing MDRP as an impurity in a solvent including methanol and/or tetrahydrofuran with at least one alkali metal periodate under conditions sufficient to oxidize at least a portion of the MDRP. MDR containing at most 5 wt% of MDRP based on the total weight of MDR and MDRP may be produced.
Synthesis and calcium mobilization activity of cADPR analogues which integrate nucleobase, northern and southern ribose modifications
Zhou, Yue,Yu, Peilin,Jin, Hongwei,Yang, Zhenjun,Yue, Jianbo,Zhang, Liangren,Zhang, Lihe
scheme or table, p. 4343 - 4356 (2012/07/02)
Novel cADPR mimics, which integrate nucleobase, northern and southern ribose modifications were synthesized. The key steps of the synthesis were a Cu(I)-catalyzed Hueisgen [3+2] cycloaddition and a microwave-assisted intramolecular pyrophosphorylation. Preliminary biological investigations showed that these cADPR mimics are membrane-permeating agonists of the calcium signaling pathway. The introduction of chlorine or fluorine at the 2'-position of the southern riboses led to a decrease of activity. The existence of a hydrophobic group on the 3'-OH of the southern riboses does not obviously alter the agonistic activity.
Ultrasound-assisted one-pot synthesis of anti-CML nucleosides featuring 1,2,3-triazole nucleobase under iron-copper catalysis
Driowya, Mohsine,Puissant, Alexandre,Robert, Guillaume,Auberger, Patrick,Benhida, Rachid,Bougrin, Khalid
experimental part, p. 1132 - 1138 (2012/08/29)
A simple and efficient synthesis of modified 1,2,3-triazole nucleosides was developed. The strategy involved sequential one-pot acetylation-azidation- cycloaddition procedure and was found to be highly effective under a cooperative effect of ultrasound activation and iron/copper catalysis. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions. This one-pot procedure provides several advantages such as operational simplicity, high yield, safety and environment friendly protocol. The resulting substituted nucleosides were evaluated for their anticancer activity against K562 chronic myelogenous leukemia (CML) cell line.
An atom-efficient and powerful method for direct esterification of silyl ethers catalyzed by HClO4-SiO2
Du, Ti-Jian,Wu, Qin-Pei,Liu, Hai-Xia,Chen, Xi,Shu, Yi-Nan,Xi, Xiao-Dong,Zhang, Qing-Shan,Li, Yun-Zheng
experimental part, p. 1096 - 1101 (2011/04/16)
An efficient and convenient procedure for direct esterification of alkyl and aryl silyl ethers with Ac2O and a catalyst system of perchloric acid immobilized on a silica gel (HClO4-SiO2) has been developed. The silyl protecting groups are directly replaced by acetyls and the protecting groups themselves are transformed into acetates as the sole byproducts, which can be readily recovered and converted back to silylchlorides, the original protecting agents, thus minimizing wastes.
