75128-73-3Relevant articles and documents
Structure and properties of 7,9-diglycosylguanine - An unstable intermediate in transglycosylation of guanine nucleosides
Boryski, Jerzy,Manikowski, Andrzej
, p. 1057 - 1059 (1999)
7,9-bis[(2-Acetoxyethoxy)methyl]-N2-acetylguanine (1), an unstable intermediate in the 7→9 transglycosylation of acyclovir, has been isolated and characterized by spectroscopy and chemical degradation.
Production method for diacetylacyclovir
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Paragraph 0020-0067, (2020/03/05)
The invention provides a production method for diacetylacyclovir. The production method comprises the following steps: (1) adding anhydrous toluene, diacetyl guanine and p-toluenesulfonic acid into areaction kettle, carrying out heating and refluxing, wherein a mass volume ratio of the diacetyl guanine to the anhydrous toluene is 1: (4-5) kg/L and a mass ratio of the diacetyl guanine to the p-toluenesulfonic acid is 1: (0.02-0.03); (2) keeping a temperature to be 103 to 115 DEG C, and adding 2-oxa-1,4-butanediol diethyl ester within 50 to 75 minutes, wherein a mass-volume ratio of the diacetyl guanine to the 2-oxa-1,4-butanediol diethyl ester is 1: (1.05-1.3) kg/L; (3) carrying out heat-preserved refluxing for 50-75 minutes; (4) maintaining a reflux reaction, and slowly evaporating methylbenzene at normal pressure within 16-18 hours; (5) adding anhydrous methylbenzene in 5-7 hours after methylbenzene is evaporated out; and (6) after a reaction is finished, carrying out cooling to 30 DEG C or below, the performing centrifuging, and carrying out drying to obtain diacetylacyclovir. According to the production method, reaction temperature is reduced, a main reaction is relatively highin safety and stability, reaction time is short, energy consumption is low, and yield can be increased to 93% or above.
Method for synthesizing acyclovir and ganciclovir by carbon-hydrogen bond activation
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Paragraph 0020; 0024; 0025; 0026, (2019/01/07)
The invention discloses a method for synthesizing acyclovir and ganciclovir by carbon-hydrogen bond activation and belongs to the field of organic synthesis. The method comprises that inexpensive guanine as a raw material undergoes methyl protection on 9th NH, a high-valent iodine reagent and monoacetyl-protected ethylene glycol or 1, 2-isopropylidene-protected glycerol are added into the raw material under catalysis of palladium acetate, the mixture undergo a heating reaction to produce acetyl-protected acyclovir or acetyl-protected ganciclovir, and the acetyl group is removed by an inorganicalkali alcohol solution so that acyclovir and ganciclovir are obtained. The method utilizes cheap and easily available raw materials, prevents use risk and corrosive reagents, has the advantages of short reaction route, simple operation, high atomic economy and high total product yield, provides a novel synthesis route of acyclovir and ganciclovir and has a potential application prospect.
One-pot synthesis of antiviral acyclovir and other nucleosides derivatives using doped natural phosphate as Lewis acid catalyst
Lazrek, Hassan B.,Baddi, Laila,Smietana, Michael,Vasseur, Jean-Jacques,Sebti, Said,Zahouily, Mohamed
, p. 1107 - 1112 (2008/12/23)
Natural phosphate doped with iodine or potassium iodide is an active catalyst for the one-pot synthesis of acyclonucleosides. To demonstrate the utility of the new catalyst system, the highly important antiviral drug acyclovir was directly and regioselectively obtained from NAcG with no byproducts. Copyright Taylor & Francis Group, LLC.
Engineering a selective small-molecule substrate binding site into a deoxyribozyme
Hoebartner, Claudia,Silverman, Scott K.
, p. 7420 - 7424 (2008/09/18)
A small goal: An RNA ligase deoxyribozyme is engineered to accept a small-molecule NTP substrate in a multiple-turnover fashion. Selective binding is enforced by hydrogen bonding, and structural preorganization within the NTP itself is important for its efficient utilization as a substrate. This study points the way toward a broader use of small-molecule substrates with nucleic acid enzymes. (Figure Presented)
Microwave-assisted regioselective synthesis of acyclic nucleosides through an alkylating reaction with 2-oxa-1,4-butanediol diacetate
Qu, Guirong,Han, Suhui,Zhang, Zhiguang,Geng, Mingwei,Xue, Feng
, p. 819 - 824 (2007/10/03)
An efficient and green procedure for the synthesis of purine acyclic nucleosides through microwave-assisted, alkylation of various purine nucleobases with 2-oxa-1,4-butanediol diacetate in the absence of solvent and catalyst is described. The advantages of using this method include its environmental friendliness, simple manipulation, short reaction time, high regioselectivity, and good yields.
Synthesis and comparative cytostatic activityof the new N-7 acyclic purine nucleoside analogues with natural N-9 regioisomers
Prekupec, Svjetlana,Kalokira, Blanka,Grdisa, Mira,Pavelic, Kresimir,De Clercq, Erik,Mintas, Mladen,Raid-Malic, Silvana
, p. 787 - 796 (2007/10/03)
The synthesis of the purine derivatives alkylated at N-7 (2a) and N-9 (2b) with 2-acetoxyethoxymethyl side chain, and chemical transformations of keto to chloro (5a), chloro to thio (6a) at C-6, and amino to fluoro (7a) at C-2 position of the purine ring were described. Structures of compounds were elucidated by analysis of their 1H and 13C NMR spectra, MS spectra and elemental analyses. N-7 Regioisomers (2a-7a) were evaluated for their cytostatic activities and their inhibitory effects were compared with those of the corresponding N-9 isomers. The 2-aminopurin-6-thione derivative (6a) showed the highest cytostatic activity, particularly against murine leukemia (L1210).
Regioselective synthesis of acyclovir and its various prodrugs
Gao,Mitra
, p. 1399 - 1419 (2007/10/03)
High-yield regioselective synthesis of 9-[(2-hydroxyethoxy)methyl]guanine (Acyclovir 1, Scheme 1) was achieved from guanine via trisilylated guanine. N2-acylacyclovir 9a-9b were prepared from N2, O-diacylacyclovir (4, 8b-8d) using regioselective deacylation procedure. N2-Acylacyclovir 11 and 13 were prepared via protection of primary hydroxyl groups. Three amino acid esters of acyclovir were synthesized as water-soluble prodrugs, which form protonated cations in pH 7.4 phosphate buffer. Two water-soluble ester prodrugs with free carboxylic acids, which form anionic species in pH 7.4 phosphate buffer, were also synthesized.
Natural phosphate as Lewis acid catalyst: A simple and convenient method for acyclonucleoside synthesis
Alahiane,Rochdi,Taourirte,Redwane,Sebti,Lazrek
, p. 3579 - 3581 (2007/10/03)
A new and efficient method for the synthesis of N-1/N-9-[(2-acetoxyethoxy)methyl]pyrimidine/purine using natural phosphate as Lewis acid catalyst was developed.
A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine
Singh, Dharmendra,Wani, Mukesh J.,Kumar, Ashok
, p. 4665 - 4668 (2007/10/03)
Regioselective alkylation of guanine, a long-lasting challenge, has been overcome by understanding the role of acids as catalyst in the coupling reaction of DAG (10) with OBDDA (11). The acid-catalyzed and noncatalyzed reactions of 10 with OBDDA which mainly give N7 and N9 isomers, respectively, appear to follow different mechanisms. The practical utility of the noncatalyzed reaction, which gives almost quantitative yields of N9 derivatives, is demonstrated by synthesizing acylovir/gancyclovir in high yields.
