- Synthesis of (purin-6-yl)acetates and 6-(2-hydroxyethyl)purines via cross-couplings of 6-chloropurines with the Reformatsky reagent
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A novel approach to the synthesis of 6-(2-hydroxyethyl)purines was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with the Reformatsky reagent followed by reduction by NaBH4 and treatment with MnO2. This methodology was successfully applied to the syntheses of 6-(ethoxycarbonylmethyl)- and 6-(hydroxyethyl)purine bases and nucleosides.
- Hasník, Zbyněk,?ilhár, Peter,Hocek, Michal
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- Reactions of Adenine and Its N-Exo Substituted Analogues with Phenyl Glycidyl Ether
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Abstract: The features of reactions of adenine with phenyl glycidyl ether depending on the solvent nature were studied. In DMF in the presence of K2CO3, an N9-alkyl derivative, an experimental antiviral drug 9-(2-hydroxy-3-phenoxypropyl)adenine, was formed predominantly. During alkylation in acetic acid, besides N9-, N3-, and N7-alkylation products were also isolated. Alkylation of 6-[alkyl(dialkyl)amino]purines with phenyl glycidyl ether in DMF produced N-exo substituted 9-(2-hydroxy-3-phenoxypropyl)adenine analogues.
- Neporozhneva,Studentzsov,Ramsh
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p. 2248 - 2254
(2021/02/12)
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- Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
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The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
- Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
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supporting information
p. 146 - 153
(2020/03/10)
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- Pyrimidinethione-containing purine compound and application thereof
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The invention discloses a pyrimidinethione-containing purine compound having a structure represented by a formula I shown in the specification and an application of the compound as a plant growth regulator. The compound represented by the formula I has excellent cell division activity and plant growth regulating activity of promoting rooting, increasing the yield and improving the quality, and canbe widely used for rooting, seedling strengthening, yield increasing and quality improvement of crops such as grain, cotton, fruits and vegetables or plants through the manners of treating seeds, being sprayed to roots and stem leaves, at the same time, the compound represented by the formula I has a bactericidal effect, and the characteristics of safe use, low costs, and significant effects.
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Paragraph 0018-0021
(2020/01/25)
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- Hetero-aromatic compound and its use in medicine
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The invention provides a hetero-aromatic compound or a stereisomer, geometric isomer, tautomer, despinner, nitrogen oxide, hydrate, solvate, metabolite, metabolism precursor and pharmaceutically acceptable salt or prodrug thereof, which is used for treating proliferative diseases. The invention also discloses a pharmaceutical composition containing the compound and an application of the compound or pharmaceutical composition thereof in preparation of a medicine for treating proliferative diseases.
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Paragraph 1374; 1377-1379
(2019/07/04)
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- Method for synthesizing adenine and derivatives thereof
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The invention discloses a method for synthesizing adenine and derivatives thereof. The method comprises the steps: firstly, subjecting diethyl malonate and dimethyl dioxirane to an oxidation reaction, so as to obtain 2-hydroxyldiethyl malonate; then, carrying out an ammonolysis reaction with ammonia water, so as to obtain 2-hydroxyl malonamide; then, carrying out a cyclization reaction with trimethyl orthoformate, so as to obtain 5-hydroxyl pyrimid-4,6-(1H,5H)-dione; then, carrying out a chlorination reaction with phosgene, so as to obtain 4,5,6-trichloropyrimidine; then, carrying out a cyclization reaction with formamidine hydrochloride, so as to obtain 4-chloro-1H-pyrazol[3, 4-d]pyrimidine; finally, carrying out an ammoniation reaction with ammonia water or an amine compound in the presence of triethylamine, thereby obtaining the adenine and derivatives thereof. According to the method, the raw materials are moderately-priced and readily available, the reaction conditions are mild, the reaction process is safe, the requirements on production equipment are low, particularly, the environmental pollution is light, and the yield is relatively high, so that the method is applicable to industrial large-scale production.
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Paragraph 0032; 0041; 0042
(2017/07/19)
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- A One-Pot Synthesis of Highly Functionalized Purines
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Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.
- Zelli, Renaud,Zeinyeh, Wa?l,Haudecoeur, Romain,Alliot, Julien,Boucherle, Benjamin,Callebaut, Isabelle,Décout, Jean-Luc
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supporting information
p. 6360 - 6363
(2017/12/08)
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- Synthesis of 1′-C-fluoromethyladenosine
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In search for new antiviral agents, we have been interested in 1′-C-fluoromethyl branched ribonucleosides. In this paper, we describe the synthesis of 1′-C-fluoromethyladenosine via electrophilic fluorination of exo-glycal. Copyright Taylor & Francis Group, LLC.
- Damont, Annelaure,Dukhan, David,Gosselin, Gilles,Peyronnet, Jerome,Storer, Richard
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p. 1431 - 1434
(2008/09/18)
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- Synthesis and anti-HIV activity of β-D-3′-azido-2′, 3′-unsaturated nucleosides and β-D-3′-azido-3′- deoxyribofuranosylnucleosides
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□ Since the discovery of 3′-azido-3′-deoxythymidine (AZT) and 2′,3′-didehydro-2prime;,3′-dideoxythymidine (d4T) as potent and selective inhibitors of the replication of human immunodeficiency virus (HIV), there has been a growing interest for the synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides with electron withdrawing groups on the sugar moiety. Here we described an efficient method for the synthesis of such nucleoside analogs bearing structural features of both AZT and d4T. The hey intermediate, 3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3- deoxy-D-ribofuranose, 5 was synthesized from commercially available D-xylose in five steps, from which a series of pyrimidine and purine nucleosides were synthesized in high yields. The resultant protected nucleosides were converted to target nucleosides using appropriate chemical modifications. The final nucleosides were evaluated as potential anti-HIV agents. Copyright Taylor & Francis Group, LLC.
- Gadthula, Srinivas,Chu, Chung K.,Schinazi, Raymond F.
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p. 1707 - 1727
(2007/10/03)
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- Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines
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A simple and efficient synthesis of 6-chloro-2-iodopurine from hypoxanthine has been achieved. This strategy relied on a regiospecific lithiation/quenching sequence of 6-chloro-9-(tetrahydropyran-2-yl)purine using Harpoon's base and tributyltin chloride. HMBC NMR studies on the product and intermediates confirmed the regioselectivity of this methodology. The molecular structures of the final dihalogenopurine and its 9-protected precursor were determined by single crystal X-ray diffraction.
- Taddei, David,Kilian, Petr,Slawin, Alexandra M.Z.,Woollins, J. Derek
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p. 665 - 670
(2007/10/03)
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- Synthesis of purine antiviral agents, hypoxanthine and 6-mercaptopurine
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Some potentially biologically active 6-substituted purine derivatives have been synthesized from simple organic reagents. The reaction of urea with ethyl cyanoacetate gave 6-aminopyrimidine-2,4-dione which was converted in two steps into purine derivative, xanthine. The latter was treated with formamide at 200°C to obtain hypoxanthine. The chlorination of hypoxanthine with POCl3 gave 6-chloropurine which was converted into 6-mercaptopurine via reaction with thiourea in acetonitrile, followed by treatment with boiling ethanol.
- Sariri,Khalili
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p. 1053 - 1055
(2007/10/03)
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- 2'-fluorofuranosyl derivatives and novel method of preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides
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A compound has the formula STR1 wherein R is selected from the group consisting of (C7 -C20)aroyl, (C6 -C20)aryl, aralkyl and alkylaryl, and (C1 -C10)alkyl-di(C6 -C20)aryl Si, R' is selected from the group consisting of (C1 -C10)alkyl, (C7 -C20)aroyl and (C2 -C12)acyl, all of which may be further substituted with O, S, N or alkyl, and R'" is selected from the group consisting of halogen, (C1 -C10)alkoxy, (C1 -C10)acyloxy, O-methane-sulfonyl and O-p-toluenesulfonyl. A composition of matter comprises 0.001 to 99.999 wt % of the above compound.
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- ACIDIC HYDROLYSIS OF 6-SUBSTITUTED 9-(2-DEOXY-β-D-ERYTHRO-PENTOFURANOSYL)PURINES AND THEIR 9-(1-ALKOXYETHYL) COUNTERPARTS: KINETICS AND MECHANISM.
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The rate constants for the hydrolysis of several 6-substituted 9-(2-deoxy-β-D-erythro-pentofuranosyl)purines and 9-(1-alkoxyethyl)purines have been measured at different concentrations of oxonium ion.The effects that varying the polar nature of the alkoxy group exerts on the hydrolysis of unsubstituted 9-(1-alkoxyethyl)purines are interpreted to indicate that the reaction proceeds by a rate-limiting departure of the protonated base moiety with a concomitant formation of an alkoxyethyl oxocarbenium ion.The same mechanism is applied to the hydrolysis of 9-(2-deoxy-β-D-erythro-pentofuranosyl)purines by comparing the influences that 6-substituents have on the reactivity of these compounds and their 9-(1-alkoxyethyl) counterparts.No sign of anomerisation was detected, when the hydrolysis of 2'-deoxyadenosine was followed by 1H NMR spectroscopy.
- Oivanen, Mikko,Loennberg, Harri,Zhou, Xiao-xiong,Chattopadhyaya, Jyoti
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p. 1133 - 1140
(2007/10/02)
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- Method for preparing salts of 6-chloropurine
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There is described a novel method for preparing and isolating novel salts of 6-chloropurine and strong acids. According to the method hypoxanthine is reacted with phosphorus oxychloride in the presence of an organic base to form 6-chloropurine, a solvent is added to the reaction mixture and the latter is reacted with a strong acid to form a 6-chloropurine salt which is then isolated. In a preferred embodiment 6-chloropurine is freed from the salt with water, preferably in the presence of a base. In another preferred embodiment the 6-chloropurine is aminated with various amines.
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- Preparation of 7-Substituted Pyrrolopyrimidines and 9-Substituted Purines as Potential Antiparasitic Agents
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A series of six 7-substituted pyrrolopyrimidines and two 9-substituted purines were prepared and evaluated for potential antiparasitic activity.All were inactive against P. berghei in mice.Six of the target compounds were also evaluated for antitrypanosomal activity against T. rhodensiense in mice.All six compounds were also inactive in this screen.
- LaMontagne, Maurice P.,Smith, David C.,Wu, Geng-Shuen
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p. 295 - 299
(2007/10/02)
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